Ep. 23 - Amnesty to Enforcement: Unpacking the 1986 Turning Point

Fire, grief, and policy collide when we ask a blunt question: how did U.S. immigration become a perpetual crisis, and who actually has the power to end it? We trace the story from the early quota laws through the 1965 reset and into the 1986 grand bargain, showing how three big inflection points shaped everything that followed. Then we walk through the decades of half-steps, near misses, and political brinkmanship that turned a solvable problem into a rolling emergency.

We break down the mechanics, who writes the rules, how party coalitions formed, and why Congress, not the White House, is the real center of gravity. You’ll hear why the 2013 Gang of Eight bill was the closest we’ve come to a balanced fix, how it won 68 Senate votes, and why it never reached the House floor. Along the way, we connect personal history to public choices, from family roots in Ireland and Mexico to the values that should guide humane, orderly policy. The result is a clear framework: credible border management, smarter legal pathways tied to labor demand, workplace verification that actually works, and an earned path to stability for long-settled neighbors.

We also float a hard political truth: it may take an unlikely champion to force a vote and close the deal. With enforcement dominating headlines, there’s still room for a “Nixon goes to China” moment that marries security with dignity and economic sense. If you care about real solutions over slogans, this deep dive gives you the context, the stakes, and the playbook for meaningful immigration reform. Subscribe, share with a friend who follows policy, and leave a review with the one tradeoff you think both sides should accept.

Transcript

Setting Big Questions On Immigration

SPEAKER_00 0:07

Welcome back, everybody, to the Radical Moderate Podcast. I am your host, Pat O'Brien. And the next two episodes, we're going to do a pretty deep dive into immigration. And this has been a theme of my podcast so far. And let me start with a couple of questions because you hear about ICE and you hear about deportations a lot in the news in 2026. So, first question uh do you think that the Democrats stand for open borders? This is something you hear a lot, and and we're going to be going through the history of that and and from a policy perspective and also from a political perspective. Is that is that true? Second question, kind of coming from the other side of the equation, were you livid when you saw two American citizens be killed, be gunned down in the streets of Minneapolis? Uh and you can argue about exactly how that transpired, but most people, I, me being one of them, were pretty revulsed by that. They thought it was awful. And I think these questions uh go back to the point of like, how did we get here? You know, and I think if you ask another question, do you think that the immigration policy and specifically the legislative policy that the Congress has passed? Do you think that it's broken? Most people, I would say it's gonna pull really high. Most people are gonna say, yes, our immigration system is broken. And what I want to explore in this episode, in the next episode, is how did we get here? You know, has this always been the case? And does it have to always be the case? And my answer to that is gonna be no, we can fix this. It doesn't have to stay the way it is. But I think if we're gonna really do anything about this issue, we're gonna have to understand the history of it a lot better than we currently do. So just for quick review, who is in charge of immigration policy? And it starts with the United States Congress. If you look at uh the Constitution, it says that Congress shall have the power to make all laws necessary for carrying out the execution of this policy. I mean, to paraphrase, that's that's where it starts. And so more in the last probably 20 years, and and probably especially during the Trump years, we have become accustomed to a lot of executive orders, a lot of presidential authority and agency authority. But this all goes back to the Congress. And so I'm not gonna not gonna give you the history of every act that the Congress has passed, but I do think it helps help helps us understand a little bit about how we got here. I'm gonna really focus on 1986 forward, but just real quick, went ahead and polled all basically all of the major pieces of immigration legislation since 1903. So I'm just gonna rattle a few of these off. Uh, Teddy Roosevelt, you got an immigration act in 1903 that, you know, they called it uh the Anarchist Exclusion Act. He has another one in 1907. Uh kind of there was some rising sentiment uh against Southern and Eastern Europeans going on back in 1907. 1917, Woodrow Wilson's president, and uh you had something called the Asiatic Barred Zone effectively banning immigration from Asia. So this is 1917. 1921, you have an emergency quota act of 1921, and it set quotas at 3% of nationalities, the U.S. population based on the 1910 census. In other words, we were just dictating who could come to this country based upon who was already here. So that's several acts. Then in 1924, and I know I'm talking about 100 years ago, this was a big one. During the Coolidge administration, you had the Immigration Act of 1924, and it had quotas uh reduced all the way down to 2% based on the 1890 census, severe restrictions, not just mild, but severe restrictions on southern and eastern Europeans, and effectively a ban on people coming from Asia, probably heavy with the anti-Chinese sentiment. So you you hear about a lot of anti-Chinese sentiment in now, but this is this is something we've been dealing with for a long time. Uh, this is in 1924. It established, this act established the U.S. border control. And this particular act really defined policy for 40 years. So this was a biggie. Now, I I would say in retrospect, a lot of this stuff wasn't probably very good, but this was these were the times, and at least Congress was doing something. They were doing their job, which I think you're going to find out later, they quit doing eventually. 1940, under FDR, there's an act. In 1945, there's some called the War Brides Act. I mean, you can you can see where some of this legislation comes from. 1952, there was an act that was passed, but but it was pretty status quo, if you will, for about 40 years there. And then you get to 1965, Lyndon Johnson, LBJ as president, and as we know, a lot of big legislation passed in the 1960s, and America was changed really forever on all levels. And so this act, the Immigration and Nationality Act of 1965, it abolished the national origins quota system. Remember, going back 40 years, that had been the defining principle is we're going to have quotas based upon basically the way you look, you know, and the culture that you come from. And it started putting the emphasis on family reunification and skilled workers, which really all of that still has remnants of today, 60 years later. And it essentially and dramatically reshaped U.S. immigration demographics for the rest, the rest of time in terms of bringing us up to speed. And it was very transformative. And then you really didn't have for about 20 years, you didn't have that much. In 1980, Jimmy Carter passed uh some stuff related to refugees. But most of this stuff in the intervening years between 1965 and 1986 was pretty small ball. And then we get to 1986, and you've got the immigration reform and control act of 1986. And I want to set the stage here for a second, because I just rattled off a lot of history to you. And it's important because if if we're really going to make good policy choices, we've got to understand our history. We got to quit living just in the here and now, and we've got to understand how did we get here? So immigration is an important issue to me, really for two big reasons. One, my heritage. The name O'Brien, you should be able to figure out I'm half Irish. I did the DNA test, and I'm I'm 50% Irish. We can trace our roots back to the old country in Ireland. My mother, though, was uh was from her family had come from Mexico. My mom was an orphan. She was born in South Dakota, but we didn't, I didn't know a ton about her history except through oral history. And then I went and got this DNA test, and I saw that uh her side had blood from and DNA from Mexico and Spain, even a little southern Europe, which some of that surprised me. But in general, she definitely came directly from Mexico to get here. And so I care because that is the story of so many Americans, and it's very personal to me. But the second reason, and really the more important reason why I care about immigration policy so much is this is something that we could do as a country. We just need a little bit of a nudge. We don't have to live with the situations that, you know, that if you're upset about what ICE has done under the Trump administration, I'm telling you it doesn't have to be like that. And not just the policy that he has, I don't think he, I don't think he has to do that policy, but we can fix this. But Congress is going to have to do it. So in the 1980s, you had a political situation where Ronald Reagan was president. And I want to say real quick that my father grew up a Democrat. He voted for Democrats his whole life. He was so happy that Harry Truman dropped the bomb. He believes that saved his life in World War II. My father voted for Ronald Reagan in 1980, and that was the first Republican he ever voted for. And he had all of those reasons, but the 1980s were so interesting because Reagan brings a lot of transformation, both to the Republican Party, but to the country at uh writ large. But what was so interesting is the Democrats had held the House of Representatives for 40 years. They held it from 1955 to 1995, 40 straight years continuously. And during the 1980s, there was a guy from Boston named Tip O'Neill, an Irishman, who did deals all the time with Ronald Reagan. And one of these was the Immigration Reform and Control Act of 1986. Essentially, folks, what this really was, it was an attempt at a grand bargain. Reagan allowed 2.7 million people who were otherwise undocumented to have amnesty and give a pathway to citizenship because they were already here. This particular act also made it illegal for employers to knowingly hire unauthorized workers. This is 1986. So when you think about it, you're like, sure, of course that has to be the case. But it just happened in 1986. But it was, it was um this grand bargain, as I talked about, between enforcement and amnesty. And I think it worked. It was landmark and it worked. So you're talking about 1924, 1965, and 1986. You have these landmark pieces of legislation, and then it all stops, basically. This is 2026, 40 years after what Ronald Reagan and Tip O'Neill were able to do and compromise and come together. And it was radical. It was radical to say we're going to give ammunities to these people. And it was also unpopular, particularly in the Republican base. They don't like that at all. They thought that, you know, well, they broke the law and you're just, you know, they're criminals and this sort of thing. And Reagan's like, I don't see it like that. He came from California. He was a border state governor. He just thought he was solving a problem. And I think he did a great job. And it's funny because I grew up in the 1980s as a teenager, and I did not think Ronald Reagan was doing a great job. That was kind of what was fed to me. And now in retrospect, I'm saying I wish I had Ronald Reagan back, or, you know, his type of politics. So I'm going to rattle off some other piece of legislation because this is where the thing bogs down. And we got it, it's a log jam and we got to fix it. That's my biggest point today. 1990, uh, Bush won has an immigration act. It did some caps on some things, something called the diversity lottery. 1996, Bill Clinton comes in, actually, more so on deportation. He kind of made the enforcement part of this tougher with border enforcement, some things of that nature. Also in 96, uh there was an act restricting immigrant access to federal public benefits. So this is during the Clinton year. So this is this is Bill Clinton being a centrist, and I think, quite frankly, doing a great job of what made sense at the time. 2001, not surprisingly, you've got the Patriot Act, which had some effect on immigration policy. But all of this stuff that I've mentioned since 1986 is pretty small ball. 2002, there's a Homeland Security Act. 2005, there's a Real ID Act. Not a lot really, though. Not a lot was big. So now you're at 2005. And this becomes uh an era for a period of time here of what I'll call, you know, just the log jam, the the near misses, the the close attempts to do something. So in uh 2005, you had something called the Border Protection, Anti-Terrorism, and Illegal Immigration Control Act. This was backed by Bush. It it didn't it didn't pass. Uh so we'll we'll move on from that. It passed the House, interestingly, but it did not pass the Senate. And then you have three acts, two under Bush, one under Obama, one, that failed. So the first one was in 2006. This was uh called the Comprehensive Immigration Reform Act of 2006. It was an attempt, another grand bargain type attempt, legal legalization, enforcement, guest worker visas. It passed the Senate, but it didn't pass the House. So this is Bush to George W. Bush, border state governor is his history. I believe he speaks Spanish. You know, again, a guy who I was not happy with during his presidency, but who I'm looking back with a lot more fondness about George W. Bush than I did at the time in the moment. I have more perspective now, and that's what we should all try to do. So in 2007, he tries again. He goes back to the well. And I remember a lot of this going on in real time. I'm sure you remember uh Rush Limbaugh, who I just absolutely was not a fan of, and I absolutely am still not a fan of him, you know, rest in peace. But I remember him stirring up the Republican conservative base to kill this bill. And I was like, George Bush is a business guy. He's he's a conservative Republican, he's the president of the United States. And I would argue to you that it was the Republican base that killed this, otherwise would have been very impactful in meaningful legislation. And so in 2007, probably because uh W. Bush knew he's term limited, it was a full-scale bipartisan push pairing legislation about enforcement with restructuring visas. And at the end of the day, he couldn't get it out of the United States Senate and it just died. But it was so close. And I would argue to you that in a different political time, it would have passed, and it should have passed. And I let me go back to where I started this episode. If you're upset about uh what was going on in Los Angeles with ICE and the killings uh in of two uh American citizens in Minneapolis by IC, this stuff doesn't happen in a vacuum. There is a very long history here of Congress not being able to do their job, not being willing to do their job. And I would argue too, and you can do your own fact check, but I would argue too, it's more so on the Republican side. Now, I will say probably during the whole history of immigration policy, there's probably been times where Democratic unions or unions who were supporting the Democratic Party weren't in love with immigration and people coming in. Maybe they believed that it was gonna hurt wages of people. So I'm not saying it's a 100% Republican problem. I'm not saying that maybe, but it's probably 75%. The conservative Republican base has killed this otherwise moderate and meaningful legislation. That's where I'm gonna lay the blame. So then Bush is out, and you remember Barack Obama comes in and he's got 60 Democratic votes in the Senate. So he he first goes to the American, uh, the ACA Affordable Care Act, which is commonly called Obamacare. And that was a massive political fight. But he won, and you know, ACA is still with us uh in our healthcare system, love it or not like it, but but it's still with us. But that kind of delayed his ability and his political capital to do something about immigration reform. And I'm sure he knew that he he had to pick, you know, what plane am I gonna take off this tarmac in order? And that's I'm sure what a lot of being president is, is which big priority we're gonna push first. So he went with healthcare reform, which the Democrats have been working on since the days of Harry Truman, and he got it passed, which is a massive accomplishment. As Joe Biden told him, it's a big fucking deal. So then he moves to immigration and he has he goes first with the DREAM Act. So in 2010, it's the DREAM Act, and it basically wanted to create a legal status pathway for certain undocumented people brought to the U.S. as children. You know, like you're brought here when you're three years old and now you're 20, right? And and you you're you've not hurt anybody, you're you're you're doing your thing, living your life. Maybe you're gonna be a doctor or you know, whatever, and and and contribute back to society, but you're not documented. You're not a legal person in this country because you weren't born here. And so that failed. It got 55 votes in the Senate. But the way the rules work, you to drag a filibuster, you got to get 60 votes. So he made a big push there, he couldn't get it done. Uh, and then he tr he tried some other things, but what he what he really did, and what everybody really did, is they started working together a little bit. And so, for those of you who remember, in 2013, there was an attempt at the Border Security, Economic Opportunity and Immigration Modernization Act, most people know as the Gang of Eight bill. You had, I believe, four Democrats, four Republican senators. They came together, they negotiated this bill, they knew there was a problem to be fixed, right? They they were doing their job. And I applaud them at that time for doing it. And they worked with the Obama administration. And remember, so you're in 2013, so Obama's just won re-election, he's got some some political clout, but he knows he needs to move quickly. This was a great bill. This was a great bill, but it didn't become a law. It didn't become a law. So you had 68 U.S. senators, so many Republicans voted for this. It had tremendous, tremendous uh momentum. It should have passed. And I would argue to you, and I mean you I can't prove it, but I would argue to you that the frustrations you have right now with ICE running around with masks and and killing American citizens, I think it's all needless. And I don't think it happened, have had to happen. And I think it goes back to not solving the problem in 2013. I really do. So what happened? Why didn't it pass? I mean, you had the president behind it, you had 68 senators, including many Republicans on it. John Boehner was the Speaker of the House in 2013. And John Boehner, the Republican Speaker of the House, refused to vote on the bill. He just said, We're not gonna vote on it. And I'm a political science major, and I kind of forgot, but I remember during that time period, the speaker of the house can simply say, We're not gonna vote on it. Now just think about that for a second. You know, like you wherever you work, if you just, you know, if you start telling clients, customers, hey, we're just not gonna work today, we're not gonna do our job, we're not gonna serve you food, or we're not gonna produce this software product for you, we're not gonna, you know, sell you this widget, we're just not gonna do it because we're so upset. I'm like, really WTF on this. Excuse me, John Boehner and the Republican uh House, you're not gonna vote on it. And his only rationale, as best I that I can tell, is they they had some name for it. Maybe it was the Boehner rule, I don't know. But basically he said, Well, if the majority of my Republican caucus isn't for it, then we don't vote on it. So, like that to me, that's not democracy. Okay. So I'm I'm really putting the blame on John Boehner. And maybe he's a great guy. You know, he and Obama would goff. I mean, it was maybe an attempt to go back to the days of Ronald Reagan and Tip O'Neill and personal diplomacy. And I'm sure John Boehner has his excuses. He has his constituencies that he had to report to, all that. He didn't want to lose his speakership. That's all fine. But what this program is about is being an American first. That deal should have got done in 2013. The gang of a bill was well thought out. It was good legislation, it would have solved a lot of the problems that we're having now, and it failed. And that's that's on John Boehner and everybody who wouldn't take up that legislation. In 2018, Obama tries uh uh excuse me, not 2018, obviously it was Trump, but in 2018, there's a move to do some things about DACA. It fails. DACA being these drink going back to these dreamers. 2021, uh Biden now's president. Um, there's an attempt at the U.S. Citizen Actip Act of 2021. It it didn't go anywhere. Going all the way to now the the end of the Biden term, there was an attempt at a border deal in 2024. But it was really, I'm gonna come to that in my next episode. I'm gonna come straight to the Biden presidency. But let me stop for one second and just take account of where we are. So I told you in the beginning, you know, 1924, you had a big immigration uh act that Congress did their job. I don't like what they did. They were, they were really focused on racial quotas and that sort of thing. I disagreed with the policy, but at least they did their job. They took their votes, and the citizens of the and the voters were allowed to judge that. 1965, LBJ uh term, there was a massive change. So about 40 years later, it was a massive change toward like, hey, let's open this thing up a little bit, but family reunification and and common sense type thing, skilled workers, made a lot of sense, but it probably started changing the way our country looks a little bit. Maybe that not everybody liked that. I bet people didn't like when the Irish first showed up in the boats. I don't I don't know how my my mother's maiden name was Avia. I don't know how she was received. I really mean that. I don't know that if she was received is like, hey, it's fine, it's nine late 1920s, nobody cares. Or maybe her people who are now, you know, my people weren't like, I really don't know. And quite frankly, I don't care because I've never faced any issues like that. I mean, it just I'm America, right? I'm Irish, I've got some Mexican blood, apparently, some Spanish blood, you know, I'm I'm all over the map, but I'm an American first. You know, how what my bloodlines are really shouldn't matter, and and the complexion of my skin or anyone's skin really shouldn't matter. But then in 1986, in retrospect, you had one of the best pieces of legislation that they passed, certainly in the modern era, between uh Republican president Ronald Reagan, Democratic Speaker of the House, Tip O'Neill. It created amnesty, and amnesty became a dirty word that the conservative base probably is still using, but really used during uh the W. Bush years to kill meaningful legislation. And ultimately, I'm sure, is why John Boehner in 2013 would not pass uh this substantive legislation. And so now it brings us back to where we started. So I've given you this historical perspective. And with a couple minutes left in this episode, I think that I've mostly just given you factual history here with with you know some context and a little bit of opinion. But now I'm gonna kind of focus more on like where are we today and what is my opinion of today? And so, as best I can tell, and I have looked for it, the Trump administration, so this is Trump 2.0, has made a decision that they're gonna focus exclusively on enforcement. Uh, whether you want to say that that's to look tough, be tough, whether you want to say that's to get criminals out of our country, that's all fine. I mean, let me go back to uh let's say talk more to people on the Democratic side of the equation. You missed your opportunities. You didn't have the political muscle in 2013 to get far close enough behind Barack Obama to push meaningful legislation to the finish line. You didn't vote in the right ways, right? Like in other words, the the fact there was a Republican House allowed that legislation to be blocked. I think what Boehner did was dirty. I think it was horrible, but apparently it was not unconstitutional. He was allowed to do it. So if you're mad about what's going on with the Trump administration, if you're mad about the enforcement, I get it. I would not do the executive orders that Donald Trump has done. I would not have what I will call the heavy-handed tactics that Donald Trump is doing. But folks, there's a reason why this is happening. It's because the United States Congress, over the last 40 years, did not do their job when they had the opportunity. That's it. That is the impediment. And we've actually been really close. And I don't think we're as far apart as you would think. And I want to be hopeful for the last three years of the Trump tenure. And maybe somebody will get to, maybe somebody who's listening to this podcast will say, you know, Mr. President, like in year one and year two, you really did a great job of shutting down that border. And I'm going to talk more about Biden and Trump in my next episode. But maybe somebody will go to him. I don't think it's going to be Stephen Miller, but maybe somebody else will go to the president and say, you know, you could do a big thing here. You could pass groundbreaking immigration reform. It would be what for people who know their history would say is the Nixon goes to China moment. Richard Nixon was very anti-China for his entire political career. And he was maybe the one person who could open up relations with modern China. And he did because he had the credibility. Donald Trump might be the only person who can fix this issue. And I know that sounds crazy radical to say, especially those of you who are like, Pat, what about ICE? What about all, what about all the things that the president has said? I'm like, I get it. I get it. But he is the president, right? And at the moment, he controls both houses of Congress in 2026. We'll see what happens at the end of the year. You're not going to get anything done without him. So it's really one man controls the fate of immigration control, at least through the end of this term. And that is Donald J. Trump. I don't know, I'm not hopeful that he's going to kind of do an about face and say, hey, I'm going to do this big thing. But maybe, maybe if you're a Trump supporter, uh, or maybe, you know, maybe if you're somehow you're in the Congress, you're in meaning you're an elected official and you listen in this podcast, there's a massive political opportunity here that is also the right thing to do for the country. And that is get immigration reform over the finish line once and for all. And folks, I don't care if Donald Trump gets the credit. That's fine because I'm an American first. I'm a capitalist before a political party. These are just ideas that I'm floating out there for you. I have not seen any effort. I don't think there's even been any real legislation from the Trump administration that had anything related to immigration except for enforcement. The big beautiful bill put a ton of money into enforcement. And that's fine in terms of that he's the president and he gets to do that. I just think there's an opportunity here. And I hope somebody who listens to this program will think about that, maybe connect some dots and somehow get word to someone in the White House. This is a problem that could be fixed. And Donald Trump could be the guy who fixes it. Folks, I appreciate you listening this week. And we're going to also talk about immigration policy next week. But for for now, that is the POV F POB.