S2 Ep43. The Human Side of Justice: Conversations with The Hon. Justice Juan Wolffe

In this inspiring episode of ABWilson's Heart of the Matter, host Aderonke Bademosi Wilson sits down with The Hon. Justice Juan P. Wolffe from The Supreme Court of Bermuda. With over three decades in the legal profession and more than 24 years as a judge, Justice Wolffe offers a profound look into his journey from his roots in Bermuda’s Back of Town to becoming a high court judge. 

Devoted, compassionate and deeply self-reflective, Juan Wolffe shares how his upbringing shaped his approach to justice and life. He opens up about the challenges and triumphs in the courtroom, the importance of compassion and relatability in the judiciary, and his pioneering work with Bermuda’s treatment courts addressing drug, mental health and DUI cases.

Listeners will also discover delightful personal insights into his love for collecting model sports cars, his fascination with magic and his passion for food and family. Justice Wolffe provides candid reflections on judicial mental health, the need for diversity and fresh energy in criminal law and advice for aspiring lawyers. A heartfelt advocate for growth and redemption, he encourages perseverance even in the toughest circumstances. 

This episode highlights a distinguished legal career and celebrates resilience, community and the power of positive influence.

https://www.abwilsonconsulting.com

https://abwilsonphotography.com

Transcript

Aderonke Bademosi Wilson (00:01.706)

Welcome to another edition of ABWilson’s Heart of the Matter, a podcast that uses overwhelmingly positive questions to learn about our guests, where every episode uncovers extraordinary stories of triumph, growth, and empowerment. Hi, I’m Aderonke Bademosi Wilson, and my guest on today’s show is Juan Wolffe. Juan is devoted, compassionate, and self-reflective. Juan, welcome to the show.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (00:35.630)

Well, thank you, Aderonke, for having me. It’s an honor. It’s a privilege being on your show, being invited to be on your show. I’ve seen a few of the episodes and the persons you have had on have been of very high esteem. So I don’t know why you asked me to be on your show. I guess you’re trying to be diverse in this type of podcast that you have. But it is definitely a privilege to appear on your podcast.

And of course, you in your own right are an accomplished woman. And so to be in the same space as you is a highlight of my life.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:15.894)

Okay, I see how we’re starting. Well, first of all, thank you for saying yes. I never take for granted when people say yes, and I am truly honored to have you as a guest today. And the words that I use to describe you: devoted, compassionate, self-reflective. Let’s start with devoted.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:21.774)

I…Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:43.230)

Why devoted? What does devotion look like to you?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:48.590)

Well, as I said to you earlier, I struggle to provide the sort of words and how to do it. I find it very difficult to describe who I am. I mean, you have to kind of be on the outside looking in and it’s difficult for me to do that. But it may be that I am that way or maybe it’s aspirational. Maybe I want to be those words, but hopefully I am.

So when I say devoted, I would like to think that I am a devoted father and husband for my wife and my children. Growing up as the product of a single parent and having a mother, who I will name, Gladys Wolffe, who put her heart and soul in me and was devoted to my welfare and my care, I want to emulate what she did for me. And I think that I’ve achieved half of that.

And if I’ve done that, I’m a happy person. So I strive on a fairly regular basis to ensure that I’m there for my family, my wife, my sons, my immediate family, my mother. So in that sense, I’m devoted. And I think I’m also devoted to my craft, my job, in a way which I hope that I am making somewhat of a difference to the persons who come before the courts. And so that requires a level of assertiveness, it requires a level of attention and hard work. So that’s why I hope I am. I hope I sort of live up to that description. But I do strive to be that way on a regular basis.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (03:34.544)

And you mentioned your job. Tell me about your work.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (03:40.320)

Right. So I have been in the legal realm for the past 30 years, the last 24 of which have been on the bench as a magistrate, senior magistrate, and a judge. And so I interact with persons from all walks of life, persons who are facing some of the most devastating circumstances of their lives, persons who are seeking to navigate through the justice system. And so while it can be a very stressful job, it is also a very satisfying and meaningful job to me.

I think, I mean, we often hear people saying that this was my calling or this is what the good Lord called me to do. I’m not sure if that’s the case with me, but certainly it is a profession which fits me and fits my character and fits my view of what I think, or how I think, the world should be.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (04:45.876)

And so how does compassion, one of your descriptors, how does that work with your chosen profession, and you as a family man?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (04:59.054)

Right. So, I mean, sometimes I think persons can be compassionate in a positive way and also in a negative way. I think I’m somewhat of an empath where I take on the feelings of other persons, which can be good and which can be bad. When others are going through strife, sometimes I feel that same strife.

But the compassion side of it leads me, at least in my family life, to ensure that my family are taken care of and that I am attuned to the feelings of my wife and my children. Hopefully in my job, the compassion is exhibited when I deal with persons who come into the courtrooms, persons who are facing some life‑challenging situations. I think people have this view of a judge as being this stoic person on the bench who doesn’t have any feelings at all and should not have any feelings at all. I don’t subscribe to that thought.

I think that a judge sitting on the bench must have some degree of relatability to those who come before them so that they can properly deal with them. So I think that having compassion for people, whether they be defendants or whether they be victims of crime, is an important part of my job.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (06:19.442)

And you said self-reflective. What does that look like?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (06:24.910)

I think that I can, and I do sometimes, much to my chagrin, hold myself accountable for things. I think that I can be introspective in relation to things that I’ve done, whether it be good or bad. And hopefully that would sort of change the trajectory of my behavior by being reflective. I also hold myself accountable sometimes to a fault.

Sometimes I’m overly hard on myself, I think. But for the most part, I think that being self‑reflective is the ability to look at one’s behavior, feelings, emotions, and decide whether they were appropriate in the circumstances, and if they weren’t, to modify that behavior or to improve upon that behavior. I’m still a work in progress. I probably always will be.

I have a lot of faults, I can assure you, but I try to work on a day‑to‑day basis, whether it be in my personal life or in my work life. And I think that for all of us, we often talk about perfection and what exactly is perfection. And I struggle with that sometimes, and I’ve come to learn that perfection is really subjective. It’s how you feel it should be, not what someone else defines as perfection.

And so part of my being self‑reflective is trying to make myself a better Juan Wolffe on a daily basis. There are some times I will go two steps ahead and then fall back three steps. That’s part of the process of growth. One should not expect to make strident, long strides every day in their life. Sometimes it’s the little things, the small steps. And sometimes you will go back. Sometimes you will retreat. And so for me, recognizing that that’s what’s happening to me, I think, aids in my growth.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (08:43.510)

Thank you, Juan. Thank you for sharing your descriptors. Now I’m going to ask you to please share three interesting things about yourself that our listeners may not know and your friends will be surprised to learn.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (09:01.272)

I’m not even sure I want to reveal all that. But I’m not sure if they’re interesting to other people, but they’re interesting to me. Would that be okay?Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (09:02.998)

Yes.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (09:13.430)

That’s absolutely fine.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (09:15.598)

All right, so, and this has nothing to do with law, by the way. So I am, and I’ve always been for quite some time, I would say since I was probably nine or 10 years old. I stopped for a while, and I’m just recently, in the last year or so, getting back into it. But I’m a collector of model cars. Now, the cynics out there will say, “I collect toys.”Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (09:21.120)

No, that’s fine.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (09:44.943)

They’re not toys, okay? They’re not toys. They are model cars, okay? Some of them can be very expensive model cars. And so I collect cars. I love high‑end sports cars: Lamborghinis, Ferraris, Porsches. And so I collect miniature versions of those cars. So that’s one thing.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (09:47.094)

Hahaha!Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (10:11.830)

So what’s your most prized possession? What is the one that you thought, “This is it”?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (10:19.407)

Right, my love of cars, again, from when I was like nine, 10 years old, was a Corvette Stingray, a 1969 Corvette Stingray. So I have a model car of that, and that kind of always takes me back to my childhood when I first started loving cars. If I was to pick a car that I could drive on the roads in Bermuda, it probably would be some version of a Lamborghini.

That’s sort of my prize car. But in Bermuda, you can’t have those cars. And so you just have to dream and collect model cars.

The second thing, which I think is interesting—others may not think so—but I am also a magic enthusiast. Let me explain that, because some people think, “You’re into dark magic.” No.

I, again, ever since I was young, I’ve always had an interest in sleight of hand and illusion, so the David Copperfields of the world. I’ve always been caught up in and mesmerized by those sort of things. I used to, at one time, be quite heavily involved in, not performing, but practicing tricks and all that sort of stuff. I have not done it for many years now, but I still have a great interest in it. And so I do take part, as a helper, in various magic shows and stuff like that. So that’s another childhood thing. Some people may say it’s childish, but it brings me joy when I’m on YouTube and I see a magical performance. It excites me.

And the third thing, okay, being at the weight of 270 pounds, it would not be any surprise to anyone to hear that I’m somewhat of a foodie. I love to eat. I love to eat good food. I like to go to restaurants and have good food. And it doesn’t matter what type of restaurant it is. It could be a food truck. It could be a fine‑dining restaurant. I just love good food. Recently, I have gotten into steaks, and I never really was into eating steaks. But now, for some reason, when I go to restaurants, I order steak. So I really love to eat. And being married to a woman who’s French, who also loves food, it does bring us joy when we go to a restaurant and have a good meal.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (13:09.600)

And do you cook at all?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (13:12.559)

It depends on your definition of “cook.” Do you mean standing at a stove with a pot and a pan with something in it? Is that cooking? I suppose, yes. I make a mean pesto spaghetti. And I think I am the foremost authority on scrambled eggs.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (13:39.710)

OK.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (13:40.975)

So to answer your question, no, I do not cook. But strangely enough, I do watch a lot of cooking shows. All the time. Yeah. So, yeah.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (13:54.100)

Okay, excellent, excellent. And do you have a favorite type of food? I know you said steak, but is there a particular country cuisine that you would default to?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (14:06.723)

Yeah, listen, if I was— and this is not good—but if I was on death row and my last meal had to be ordered, it would have to be anything made by my mother. And so it would have to be her greens and rice, macaroni and cheese, barbecue ribs, and her goulash. So yeah, that would be my favorite meal. I love home‑cooked Bermudian cuisine. There’s nothing better than it, no matter where you go in the world, as far as I’m concerned.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (14:57.000)

Excellent, thank you so much. Thank you. And can you tell us about a recent accomplishment or success that you’re particularly proud of?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (15:11.783)

Over the last, and this will be in my professional capacity, over the past 10 to 15 years, I have been very much a part of the implementation of the treatment courts in Bermuda. And when I say treatment courts, I’m talking about the Drug Treatment Court, the Mental Health Court, the Driving Under the Influence Court. And those have been life‑changing programs for persons who come before the courts. And I have been deeply ensconced in each of those courts.

I, in fact, was the— with the help, of course, of a team of us—we set up the Mental Health Court for those who commit crimes as a result of mental health issues, and to a large degree, to remove a lot of the stigma that’s attached to mental health and also to break the cycle of criminality for those who may be struggling with mental health issues. And the same applies to drug treatment and also DUI. And I tell you, they have been the most successful programs in the entire criminal justice system over the past 15, 20 years.

And to be a part of that is absolutely satisfying for me. And to look back—I’m no longer involved in these programs because I’m now a Supreme Court judge—but to look back and say, “You know, I was a part of that legacy,” does bring me a level of good feelings.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (17:03.830)

Thank you. Thank you for sharing that story and for sharing those successes. Please tell us about a time when you made a difference in another’s life. What were the circumstances? Paint a picture for me.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (17:18.767)

You know, in my line of work, persons don’t sort of write letters or go on the news or go in the newspapers and say, “Mr. Wolffe,” or any judge or magistrate, “has done this for me, it’s great.” And sometimes they’re not articulated and so on and so forth. But every now and again, every now and again, I could be walking on the street and someone will come up to me and say, “I don’t know if you remember me, Mr. Wolffe, but 15 years ago, you did X, Y, and Z for me in court. You could have locked me up, but you didn’t. Or, in some cases, you did lock me up. And I just want to let you know that that was the best thing that happened to me because it allowed me to change my life around. I now have a family, I have a job, I’m a law‑abiding citizen.”

And I tell you, those sort of comments warm my heart. And although they may come 10, 15, five years later, the effect of it is still quite impactful for me. In our line of work, those of us who do this type of work, we don’t do it for money, I can assure you.

People think that judges and lawyers get paid a great deal of money. I can assure you that comparatively speaking, we don’t. But where we do get our satisfaction is in helping others navigate through what can be some really serious life issues. And to be a part of that, and that you actually made a difference, I think, has more value than any paycheck that could be received.

And so, yeah, it’s those personal stories that every now and again come back to remind you that this is why we do what we do.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (19:33.482)

What were the key strengths and qualities you relied on to make a difference?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (19:42.444)

Again, I’m not sure I can put my finger on that, but I think that it’s my relatability to the persons who come before the court. As I said, and you would know, Aderonke—people know your humble beginnings—but we share very similar stories in that regard. So persons who come before me may have, like me, not had a father in their life, or they came from a depressed neighborhood.

I am a product and a proud product, and I wear it proudly on my sleeve, of the Back of Town area. I was born and raised in the Back of Town area: the Victoria Streets, the Curbs, the Middletowns, the Dundon Streets, the Union Streets, the Court Streets.

I acknowledge from whence I came, and persons who come before the courts come from similar circumstances. And so when they come before me and say that they did X, Y and Z because they needed to feed their family or they needed to get Pampers for their child, I understand that struggle because I’ve seen that struggle up close and personal. My mother worked three jobs, and she worked extremely hard to provide for me. I never wanted anything, but that was because she made a great deal of sacrifice. But for the grace of God go I. I could have gone in another direction. I didn’t. Some of my friends did. That doesn’t make them less of an individual. It’s just that their circumstances led them in a different way. And so when persons come in front of me, I can relate to their struggle. They don’t think so at first.

When they come before me, they think I’m just this guy who doesn’t know anything about it. But when I do start telling them where I came from, and when some of them come before me, I know their families. And I’ll tell them where their family stayed, whether it be top or bottom row of Middletown, or “Your family lived on The Curb next to the bakery, the Curb Bakery.” And when you do that, you can see a person’s guard being let down.

And I’m able to better assist them in getting through whatever issues they may be going through. The other thing is that I think we have to understand that not everyone who commits a crime is a bad individual. Persons commit crimes for a plethora of reasons, some of which are beyond their control. And again, coming from the area where I come from, I understand that. I understand that just because you commit a crime, or just because you’re a drug addict, does not make you a bad person. Not at all. You may be an individual who has, because of drugs, done bad things, but it doesn’t make you a bad person. And I didn’t need to have a university degree to tell me that. I learned that from being on the streets, playing on Court Street, being at DeGraff’s Bakery.

My mother used to work on Court Street as a waitress. So I was on Court Street all the time and seeing people all the time who may be involved. And back then, Court Street was the place not to go. But seeing all that, and knowing that, “Wait a minute, these are some good people. People who I would rather, even today, probably deal with more so than some persons from Front Street,” because there’s a realness about them that I think I can relate to.

So, yeah, I think it’s the relatability that allows me to do my job in a way which I think, hopefully, is effective.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (23:42.039)

You’ve talked about your career a lot. Did you have aspirations of being a lawyer or being a judge when you were growing up and looking at your childhood circumstances?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (23:59.185)

I did not want to be a lawyer. I mean, people have these romantic stories about always wanting to be a lawyer since they were five, and “I was always arguing.” That’s not my story. I chose to become a lawyer as a matter of practicality. I was on track to be a forensic psychiatrist.

Working as a police officer, coming across many young men who were involved in criminal behavior, it was fascinating to me why persons were involved in that and that some of them may need assistance. And so I left from being a police officer to go and be a forensic psychiatrist. It was during the time of my first degree that it became clear to me that it was going to take an additional eight years to become a doctor of psychiatry. That was eight years of money, and I did not have any money. And so, at the time, a lot of my friends were going to do law. And so I said, “How long does law take?” And they said, “Oh, about three years.” I said, “Well, I’m not a great mathematician, but three years is far shorter than eight years. Maybe I should do that three‑year thing.” And so I just decided, “Well, let me just go do law.” And I applied to a school, I got in, and I literally left and went to law school.

Now, having said that, once I became involved in my legal studies, I really started to love the law. And that might sound really nerdy. But I really started to love the law and its effect on society and its impact on society. And that’s when I said, “I think I actually quite like this area.” And ever since, I’ve had this sort of passion for everything law.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (26:21.700)

So that which I did not have any clue about, did not have any interest in, I actually gained a great interest and liking for—probably more than I would have had, had I become a forensic psychiatrist. Does that make sense? So here I am, faced with a situation of just practical circumstances, but it ended up being a feature of my life which was going to be very meaningful. And I met my wife at the university that I was not supposed to go to. And, you know, she’s my wife of 30‑something years. And we have two wonderful boys. And so who would have known, right, how your life kind of changes its direction. You never know why it happens, but what happens can actually end up being a better plan than what you originally had.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (27:21.951)

I have two questions. What is a forensic psychiatrist? And second, what guidance would you give to a young person who may be interested in law?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (27:35.505)

So forensic psychology is, in the most basic definition, looking at, for me in particular, criminal behavior and what are the criminogenic needs that a person may have to assist them in avoiding criminal activity. It’s trying to understand the criminal mind: why do people, from a mental perspective, commit the offenses that they commit? What are the mental precepts for that behavior to take place?

It could be a broad range of things. It could be behavioral issues. It could be more acute psychological or psychiatric issues, such as schizophrenia or depression or whatever the case may be, and assisting those individuals with trying to navigate through their mental challenges to ensure that they do not commit crimes again and helping them understand the origins of their criminal behavior.

I, and I don’t know if this is interesting—it’s probably macabre and maybe even kind of depressing—but at one time, and this might have been the reason why I was so interested in becoming a forensic psychiatrist, I had this—“fascination” is the wrong word, so I don’t want to use it—let’s just use the word “interest.” This interest in serial killers and why do serial killers kill the way that they kill. I hope this is not too depressing, but I kind of low‑key studied the behaviors of the Son of Sam, Charles Manson, and people of that ilk, and why do these guys go and do what they do? And now I kind of look at the school shootings in America and I’m trying to figure out why would a person go into a school with a gun and kill innocent kids.

And that kind of, in a strange way, fascinates me—why they would do that sort of stuff. What was in their minds, what was going on in their minds, that would allow them to go and do such a heinous, heinous crime? And so, yeah.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (29:59.307)

Thank you. Thank you. Thank you. Wow. OK. So what guidance would you have for a young person or even an older person who may be considering law as a profession?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (30:13.776)

I can tell you this here now, that I can speak to the law that I do. I can’t speak for corporate law or anything. But I can tell you this without any fear of contradiction: if an individual chooses to engage in law in which they’re dealing with victims of crime or defendants, it is never a dull moment. A day is never dull.

It’s always filled with drama and excitement, but it is the most meaningful and satisfying job that you probably could do, because you are helping people to ensure that their constitutional and legal rights are being looked after. And I’m talking about people who are some of the most heinous criminals that we may have, helping them understand and helping them get through a system which they sometimes, justifiably, but I think most times unjustifiably, feel is against them.

And I think that as an individual, as a lawyer doing that type of work, you won’t get anything more meaningful—maybe except being a doctor. But the other thing about being a lawyer as well, I think it is so marketable that it can translate and be transferred to other areas. So a lot of lawyers work in other fields like insurance or in business, as analysts. Doing law is a great, great, great foundation from which you can do other types of things that may not necessarily be strictly law, but draw on a legal background. Because as a lawyer, it shows any employer that you have the aptitude to analyze things and that you probably have fairly good written and verbal communication skills.

So I would definitely say to anyone who’s choosing to do it, get into it.

And just so your listeners can understand: a law‑school program normally takes about three years, and then you have to do what they call your bar exams, which takes a year, or you do a Solicitors’ Finals, which is about two years, and then you have to do what they call a pupillage. In Bermuda, a pupillage is for a year. So the entire process before you can start calling yourself “I’m a lawyer” can be about five years.

There are some great schools in England and they’re fairly well priced. Of course, if you go to the United States, it can’t be because that’s United States law, but anywhere in Canada or England—Canada’s prices are a bit better than America’s—but most people in Bermuda go to England. There are also some really good schools in the Caribbean. In Jamaica, I think it’s the Norman Manley Law School, and I want to say in Trinidad it’s the Hugh Wooding Law School, but they also have law programs, so they’re very good. The professors in the Caribbean are excellent. And that is even a shorter program. So if anyone, whether you’re 21 or 55, you could, in four to five years, be a fully fledged lawyer, and not at much expense.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (33:34.583)

Thank you.

Okay, that’s a great promotion for your profession. So thank you. Thank you.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (33:44.977)

And—sorry, sorry, everyone—the criminal defense bar is very small. So we need criminal‑defense lawyers. The ones who are working very hard, they’re very good, but they are getting a bit long in the tooth. And I don’t think they would have a problem with me saying that. I mean, they’re working extremely hard. We need to have new blood. We need to have an influx of young persons who want to do criminal law, who want to be criminal‑law lawyers. Most lawyers who go through the system choose to do corporate law. That’s for whatever reason.

So we need to attract persons who want to do criminal law so that we can ensure that persons’ legal and constitutional rights are being observed.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (34:42.081)

Thank you. Thank you for that.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (34:46.639)

Juan, can you recall a situation where you overcame a challenge that led to personal growth? What did you learn from that experience?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (34:57.648)

I don’t think that it was one particular event. I think it’s probably an accumulation of things, I suppose. I think that we all go through periods when we fall short of what we expect of ourselves, or of what people think about us, or small failures here and there. So throughout my career—and I think it has to be said—as a young Black man trying to navigate through a whole plethora of things, being accepted in a profession which ostensibly was seen as a white profession,

being confronted with situations of racism, being confronted with confidence‑devastating blows over a period of time and how you come out at the other end of that is something I think that people should be proud of, if it happens. And so for me, I think it’s just a series of things that happened over time that I had to navigate through, and rather than taking a route which was depressive, I took a route which was like, “I’m going to show them that I can do it.” You know what I mean? Yeah, so for me, it’s just not one particular thing.

And also, as I said to you before, financial issues, having to get through university. Every year I was in school, it was always a challenge as to whether or not I was going to go back the next year. Every year. Every year I ran out of money. Every year I had to get another job. And my mother, again, worked extremely hard, and if it wasn’t for her, I wouldn’t have been able to go, period. But even being in university, having those difficult exams to do, particularly in law school, and just thinking, “Why am I doing all this? I’ll just go back and do something else. It’s just too much of a burden on me. I don’t only have to worry about school. I’ve got to worry about whether or not I can eat next week.” Those sorts of things.

Then coming back and trying to find a job in a profession which did not, at the time, necessarily view persons like me as being equal. You know what I mean? And so, you know, applying for jobs and not getting jobs when I knew I was more qualified, or seeing people being given jobs when I knew that I ran circles around them professionally and intellectually and academically. And kind of being able to get through all that. And even today, even today we have our challenges, right? In different ways. And so I just think that life shows up every day and there are going to be good things and bad things.

Being able to navigate through and surmount those everyday challenges, I think, is success. And again, sometimes it’s the little things. And I learn a lot from the persons who come to the courtroom, persons who have some serious issues, far more serious than mine. And to see how they have taken redemptive efforts to change their lives around is inspirational.

So, yeah, it’s just the little overcomings of challenges that life kind of throws at you which I think lead to growth. What is the saying? “If it doesn’t kill you, it makes you stronger.” And you kind of live by that, right? Life’s going to show up every day.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (39:17.717)

You are listening to ABWilson’s Heart of the Matter podcast.

Welcome back to ABWilson’s Heart of the Matter. My guest today is Juan Wolffe. Juan, we have talked about your legal career. We have talked about your time on the bench. We’ve talked about your model‑car collection, your life as a family man. What self‑care practices or strategies help you to sustain your energy and motivation while navigating your journey?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (39:57.147)

Going home. Going home. Listen, my home is my sanctuary. It’s where my wife is, it’s where my family is, and it’s out of the public spotlight. I don’t have to deal with a lot of issues that I have to deal with. And so I go home and I just vegetate and just rest, and my family allows me to just do that and decompress. And that helps me with my mental health, just being able to disconnect from a world which is chaotic to me.

But I will say this to you, that in the judicial world, judicial wellness is a very hot topic right now because what we’ve found is that judges can suffer from PTSD, particularly those who deal with the most horrendous cases, and over time it takes its toll. And so I think that we need to do a better job, as judges, attending to our mental‑health needs.

And again, the way I deal with it is to go home and be with people who I know support me and people who I know love me unconditionally and who I love to do things with. And so my wife and I love to travel. And so every now and again, I need to get off the rock and kind of change the channel a bit and see different things. Because the work that we do is extremely serious. And sometimes I need to be silly about things because 90% of my day is about being serious. And so I will go and watch a bad movie just to kind of unwind.

You know, my only problem right now though is that I’m obsessed with the American political system. And so I’m watching way too much news about the American political system. Much more than I should be. But yeah, so to answer your question, it’s not really a strategy. I think that obviously it’s specific to you and what works for you. And what works for me is to go home and be with my family.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (42:47.223)

You’ve mentioned judicial mental health. That’s something that I personally have never considered. And you’ve raised it as a topic that is being looked at more and more. What is being done to help judges? Because we look at the victims, we look at the perpetrators of crime, we look at society in general. But I must admit, I’ve never considered the lawyers or the judges in cases, especially really, really tough cases.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (43:23.130)

Well, let’s put this into perspective. Every day that I come into work—and this probably applies to prosecutors and to defense lawyers—on my desk is murder, rape, drugs, serious sexual abuse, sometimes involving children, theft. There’s nothing positive about any of those things. Nothing. And so if that’s all you see every day, for 365 days of the year, for the last 15, 20 years, then it does play on your mind and you need some sort of release from that. One may think that we can just simply deal with these cases. Let me just say this here: we are human. We’re human. We’re not just these sort of cold, callous individuals sitting on the bench. We are human. So when we hear human stories, we react in a human way. And while it may not be an outward view, something kind of percolates within you. And after a while, you feel drained.

And so what has been recognized is that judges need to be able to find a way to deal with that, particularly those involved in the criminal realm, because there is a psychological, maybe even a psychiatric, effect that may be having on an individual. So it’s not unusual, not so much in this jurisdiction, but in other jurisdictions, where judges—there have been judges who have committed suicide. There are judges who have marital issues. There are judges who unfortunately have turned to alcohol or drugs because of the nature of the work that they do.

And so what is being recognized is that, as part of any judicial terms and conditions, there needs to be a mental‑health piece put into it where it is not mandatory, but it is absolutely a requirement that there be mental‑health services available for judges to be able to deal with those sorts of issues.

I can’t speak for lawyers or judges who are in other areas of law. I’m sure that their work is extremely stressful. Our work is stressful, but with the added element of looking at probably some of the lowest forms of depravity that you can see. For example,

every crime or every incident, whether it be murder or whatever, or a fatality in Bermuda—let’s just think of anything that’s happened in the last day, two days, month, two years, whatever—I will see all of that. I will know about every single bit of that murder that took place at some point in time, every little intricate detail of what took place. You may know that the murder took place, but I will be dealing with every minutia of that case at some point in time. You know what I mean? So when you start seeing images of murder or images of persons being shot, photographs, autopsy photographs, all of that,

yeah, it takes its toll. So if I’m doing a difficult case, for example, that involves all of that, plus another deal of all sorts of other legal issues, my weekend is spent pretty much unwinding from all the stuff that took place. And on top of that is ensuring that a defendant has a fair trial. That in and of itself is a stressful endeavor, and also ensuring that any victims also have a fair trial. And so it’s that added element as well, making sure that you make the right decision in some of the most legally sensitive, delicate, and complex issues, which again can take its toll.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (48:06.005)

Juan, thank you for sharing this side of the legal system that I will say I had never considered. So I appreciate you giving us a glimpse into it. Thank you.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (48:25.337)

No problem.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (48:26.721)

How might sharing your experiences of success and growth create a positive ripple effect in your family, community, the world?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (48:39.632)

I mean, again, it gets back to from whence I came. I think that there are many people who come from depressed areas or are faced with these sorts of circumstances and feel that they are less than, or that they’re not good enough. I can tell you that many of my friends who I ran around with when I was young in the Back of Town area, many of them were more intelligent than I was, more academically gifted than I was. But for whatever reason, they found themselves in some serious situations. And so I just want to say that just because you may come from that area, or just because you may have been raised by a single parent, or just because you may have some issues, it doesn’t mean that that defines who you’re going to be.

Who I am, where I came from, is still very much a part of me. It defines part of who I am. And as I said earlier, I wear it on my sleeve, where I came from. But even those who are in the most dire of circumstances—and there were times when I certainly was in some serious financial dire circumstances—you can grow from that.

Even though you may find yourself in the worst of situations, there is a level of redemption that you can enjoy. You can rise like the phoenix from the ashes. And I know that sometimes when you’re deeply mired in the problems that you have, you don’t really see that. And you want things to happen right away. Many times it doesn’t happen right away. It could take days, months, maybe even years. But if you keep striving towards it, then it can happen. But also, surround yourself with positive people who are going to support that growth. Because if you don’t have that, then that could be problematic. So I just hope that people can see that this little Black boy from the Back of Town area can, with some degree of help and with assistance, certainly from my mother and my grandmothers, sit in this seat of justice in Bermuda one day.

And although it may seem bleak when you’re kind of deep into it, do not lose sight that the possibility is always there. But it’s going to take work on your part, obviously. It may take some work on the part of other people, but it’s not an insurmountable task. And there are going to be— I mean, it’s a cliché, but it’s true—there are going to be ups and downs.

There are going to be setbacks. But you’ve got to keep pushing forward with it. I’m still growing. I’m still growing. I’m not the complete version of myself yet. I will be. I’m not going to tell you what my age is going to be when that happens. But I’m still, as I said earlier, a work in progress. And that’s the way I want it to be.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (52:06.261)

What exciting opportunities do you see on the horizon? How do these opportunities align with your passions and aspirations?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (52:17.156)

For me personally?Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (52:18.263)

Mm‑hmm.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (52:22.648)

I see retirement in five years’ time as being an exciting opportunity on the horizon for me personally. I will be 65 in five years’ time. I’ll be at retirement age. And I think so far I’ve had a pretty good innings. But I think that it’ll be time. It’ll be time for me to kind of disconnect from all of this.

Disconnect from being somewhat of a public figure and what that means, and what comes with that. The stress and strain of being a judge. I look forward to that eventuality. I know that some people, when they retire, don’t know what to do with themselves. I know exactly what I’m going to do with myself. I can assure you.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (53:21.781)

What would that be? Can you share?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (53:49.807)

Well, put it this way: it’s going to involve a lot of eating. It’s going to involve traveling. It’s going to involve some reading. It’s going to involve just sitting around the house doing nothing and not having to worry about doing anything. And so I look forward to that. In fact, that’s my motivating force now: work hard now because, guess what, in five years’ time, you’re outie. And I’m looking forward to it. And that’s because I think that I have—so far, I’ve still got work to do—but I’ve put the work in. And it’s now time for me to rest. And also to spend more time with my family, my wife. And so, you know, she will be hitting that age as well. And so that’s kind of our plan:

to enjoy the remaining, the balance, of our lives. You know, when you get to my age, you start having these thoughts of your personal mortality. And so you want to kind of ensure— I don’t want to see myself working, at least not having to work, at 65. I mean, I know that some people do, because of their personal circumstances, and I glory in their spirit.

I don’t see myself wanting to do that. I hope that when I get to 65, I can sever myself away from all of this that I have to deal with on a regular basis.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (55:04.919)

Thank you.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (55:06.352)

I can talk about the courts now—what’s on the horizon for the courts. That’s my personal opportunity.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (55:13.835)

Do you want to talk about the courts?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (55:16.184)

No, not really.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (55:17.673)

Okay, Juan. What brings you—Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (55:19.364)

I mean, real quick, there are things I think which are exciting that are happening in the courts. I mean, we are ensuring that persons understand proper sentencing guidelines. I think that we are moving towards an electronic system for the courts. I look forward to seeing a lot more of the treatment courts. So I think there are a lot of good things that are taking place. Our current Chief Justice, Larry Mussenden, is quite a progressive person and so he’s doing a lot of good things for the court. So I think that the Bermudian public will be really well served in the criminal‑justice system over the course of the next few months but also years.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (56:17.429)

What brings you joy?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (56:18.128)

Yeah, it gets back to my family.

I’m trying not to sound cliché and all that.

My family is really my go‑to when I need to put things into perspective. So, for example, I may be this so‑called “big‑time” judge, but I can tell you right now, Gladys Wolffe ain’t having none of that. My mother grounds me on a regular basis: “Hey, don’t you… where do you think you are?”

My mother, my wife, they let me know that being a judge does not define who I am as a person, nor should it. It’s something that I do. I like doing it. I love doing it. But it’s not who I am, if you understand what I’m saying. And so my family brings me back down. If ever I think I have a big head or I’m getting too uppity, my family brings me back down and I’m grateful for that. I’m really grateful for that. And so when I see the smiles on my mother’s face, my wife’s and my sons’ faces, yeah, it brings me joy. It brings me joy. Especially again, since during my entire day I’m seeing nothing but frowns and negativity. They bring me positivity.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (58:00.863)

So we’re nearing the end of our time together. What book recommendation do you have? It can be a book that you’ve read recently or something that has stayed with you over the years.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (58:14.724)

So I like reading fiction novels. That’s my phone, sorry. I like reading fiction novels, in particular I like reading assassin‑type fiction novels. However, there was a book that I just recently read—I don’t know, when I say “recently,” maybe within the last six months. It’s called Black AF History: The Un‑Whitewashed Story of America, and it is written by an author called Michael Harriot. And what he does is he gives the story of America from the perspectives of former slaves, persons who were involved in the civil‑rights movement, and he fills in the gaps of things which the traditional history books did not tell you. And so, for example, he would tell the stories of various different slave revolts that took place on various plantations in the South that I’ve not even heard about.

But it tells the story of the struggle of the slave: what they had to go through, what they went through. And he has empirical evidence to back up all this, by the way, and it’s an acclaimed book. And so, you know, we often hear that history is often the narrative of someone else who had the veritable and the means to tell that story and to project it out there, right? Well, he gives the other version.

And it intrigued me because, as a judge, I’m always kind of looking for what’s the other side of the story. The history books that we look at tell it from the eyes of a person whose skin is lighter than me. That’s not a criticism, it just is the way it is. But I always wonder about:

Why don’t we hear more stories? I mean, we know about Harriet Tubman, we know about Rosa Parks, but there are many other, some will argue, far more impactful persons than Harriet Tubman and Rosa Parks and, you know, even to some degree I dare say Martin Luther King. There are people who played integral roles during slavery, during the civil‑rights movement, who you never know about, but did phenomenal work. So, for example, Rosa Parks, who is the icon of the civil‑rights movement, but the story goes that there was another woman—I forget her name—who actually refused to give up her seat on the bus before Rosa Parks did. And so those sorts of things intrigue me, like finding out additional information. And so this book did that for me.

It filled in a lot of spaces, but also gave me an even greater appreciation for the struggles and the challenges that slaves had in America. Even stories like during the Civil War in America between the North and the South—we don’t hear that many stories about the soldiers, the Black soldiers, who played an integral role in the North winning that war.

You know, Bob Marley has a song called “Buffalo Soldier,” right? But there was a huge contingent of Black soldiers who made a vital impact on that war, and you hardly hear about them. And this book kind of tells those sorts of stories, and I found it quite intriguing. So anyone wanting to pick it up, I would say it is for all races, it is for all genders. It’s a book that kind of gives—and what I like about the book, it’s not a book that lambastes white individuals. It’s not one of those types of books. It’s not a “complaining” type of book. It’s just a factual book that says, “These are other things that took place that you should know about.”

I also like the style in which he writes it. It’s very relatable in terms of the words that he uses and the turns of phrase that he uses, which I thought were quite humorous as well.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:03:10.025)

Juan, thank you so much for your time. Thank you for your candor. Thank you for your insight. Do you have any final thoughts?Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:03:23.556)

I do not. I just want to thank you for providing a voice for not just persons like myself, but for the persons in the business realm, and providing a channel through which persons can be educated about various different things that they ordinarily would not know about. So kudos to you and your team for doing the great work that you’re doing. And I hope that what I’ve said resonates with at least one person and that I fit within the high standards that you’ve set for this podcast. And I also hope I can be spoken of in the same sentence as all the other persons who are guests on your program. So thank you very much for inviting me.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:04:15.247)

Juan, thank you. And I appreciate your kind words. And I want to just give some appreciation nuggets from our conversation. One of the first things that you said earlier in our talk was, “But for the grace of God go I.” And that’s something that I absolutely can relate to. And you’ve talked about your upbringing in Back of Town and that for people who may not be from Bermuda, it is a geographical location in the center of the island that has historically not necessarily been a wealthy area. I think that’s a way that I could describe it.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:05:04.836)

Well, I suppose it’s the equivalent of the inner city that persons would talk about, where persons who live in that area are, for whatever reason, not as financially secure as they would like to be or even strive to be. Unfortunately, it’s an area where there is criminal activity, probably more concentrated than in other areas, at least when I was younger. But I think, I still think, that it’s the heart of Bermuda—at least, again, when I was growing up, it was the heart of Bermuda. That’s where you had Mr. and Mrs. Bermuda. And so it’s also the area that I think is the most underserved area in Bermuda. I think that we need to do, and those who are in power need to do, more to uplift that area. I know that it’s a complex issue.

But I think that more time and energy needs to be spent in terms of uplifting that north area of Hamilton. And I do think the people who live there deserve it. I truly believe that. And again, I hate to—I know that you’re the interviewer and you don’t like to be brought into these sorts of things, but I’m going to bring you into it. I mean, you know the situation, right?Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:06:34.327)

Well, and I think back to even my childhood where we lived on Dundon Street, immediately beside Place’s Place. And people outside of Bermuda may not know where that is. And I remember when we first came to Bermuda, we actually lived on Court Street. And then as teens, we lived on Elliott Street. And these are all areas immediately in the Back of Town area. So that is part of my DNA. That is part of my heart. And not just mine, myself and my two brothers, having grown up there. And we refer to it. We know that that is part of what makes us who we are today.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:07:28.720)

Listen, I tell people every time, “Listen, don’t let me get Back of Town on you. Don’t be fooled by this robe. We can deal.” And when I say that, I’m not talking about in a violent way. I’m just talking about in a way where I’m not going to back down from you. My DNA, my upbringing, tells me that I’ve got to fight for everything. And not only that, but I’ve been through adversity, financially and otherwise. And so what you say to me doesn’t really… listen, we can deal with it, right? And so you either have me as sort of the nice, genteel judge, or the Back of Town me. Which one do you want? Because either way—and, as I said, I wear that proudly—there’s a certain mentality and personality that a person from the Back of Town has that, look, listen, I’m going to deal with you. I’m going to hold you accountable. I’m not going to sort of beat around the bush. I’m just going to let you know, because that’s where I come from. I’ve had to go through all this sort of stuff. I had to navigate through the streets of Back of Town

to worry about, in some cases, drug dealers or some guy who’s trying to beat me up. You know what I mean? I’ve had to get into physical fights to prove who I am. “Listen, if you want to be a thug, we can do that.” And sometimes I’ve got to kind of step back from it. You know what I mean? We don’t have to go there, but trust me, if we have to go there, we can.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:09:25.044)

If we have to, we will.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:09:27.566)

We can do that. So, yeah. So just for your listeners, the Back of Town area, I suppose, would be equivalent to maybe Harlem in New York, maybe, or an inner‑city area. Back when we were growing up, the Court Street/Back of Town area was the no‑go area for the rest of Bermuda. I mean, I had Black friends who said that their parents told them not to walk through Court Street or not to drive through Court Street. I’m like, “But that’s where I play.”Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:10:06.135)

But Juan, let me just say this: it was also a community, right? And when I look back, especially as a teenager, an older teen moving back to Bermuda, it was a community. And I think about, especially my brothers—because they’re slightly younger than me—and us being of that community and knowing our neighbors and being neighborly, even though it was Back of Town. You still had that community spirit. And I still will periodically drive through the area and see how things are going, see what’s going on. A new building here, a renovation there. And I’m still curious about the neighborhoods and the streets that we wandered.Transcript-Juan-Wolffe-10-25.docx​

Juan Wolffe (01:11:04.740)

That’s what people don’t understand, right? That there was a level of community there that I think surpassed many other communities. So I knew that I could go next door and get some groceries because they understood that my mother, for this week, couldn’t afford to get the milk. So they had the milk, right? And even kind of looking out for you. I have a quick story—I know you’ve got to go.

So I became a police officer, right? And I was always assigned to the Back of Town area to do walking patrols. And the reason being is because I never had any issues walking Back of Town. Not only that, but all the guys who were in Back of Town didn’t have any issues with me walking Back of Town in my police uniform because they knew me

growing up. And so, whatever they were doing, if they saw me, they would stop doing it out of respect for me. And again, that was kind of born out of, I think, a commonality of strife, where we were all struggling, but there was a level of togetherness in that struggle which helped you, I think, move on. So my mother, my friends—some of them were hardened criminals—but good people. You know what I mean?

And so I’ve had situations when I was a police officer where people would not bother with me because they knew who I was and they respected that. And I had a few of them come up to me and say, “You know what we’re into. But look, listen, we respect your decision to become a police officer and we support you. We won’t tell you who’s committing crimes, but we’ll let you know that you’re not going to have any problems.” You know what I mean? And so, as I said, growing up in the Back of Town area is very much a part of my heart and I’m glad that I went through it.Transcript-Juan-Wolffe-10-25.docx​

Aderonke Bademosi Wilson (01:13:27.407)

And I appreciate the sharing. There’s not a lot of people that are able to reflect back on that time in the 70s and 80s and the communities that were built and continue to exist in those areas of Bermuda. So two more quick appreciation nuggets. You spoke very clearly about criminal law

being the most meaningful and satisfying job you can do. And one more is:

Just because—and this speaks to what we’ve just been talking about—just because you may have come from that area doesn’t define who you are. You can grow from dire circumstances. Juan Wolffe, thank you so much for being a part of today’s show. I appreciate you taking the time to join me on ABWilson’s Heart of the Matter, a podcast dedicated to asking overwhelmingly positive questions as we uncover incredible stories and wisdom of people you may know. Juan Wolffe, thank you so much.

Juan Wolffe (01:14:47.460)

Thank you.