2026 Strategy: Why Kentucky Matters — A Conversation with Prominent Democratic Strategist Andrew Grossman

In this episode of The Blue Dot Podcast, hosts Natalie MacDonald and Brian Koehl are joined by longtime progressive strategist Andrew Grossman for a wide-ranging and hopeful conversation about the road to 2026.

Andrew brings decades of experience—from serving multiple cycles as Director of the Democratic National Convention Platform Committee to leading major national field operations—to break down why the fight for the House of Representatives runs straight through places like Kentucky’s 6th Congressional District..

The conversation dives into the energy sparked by the No Kings movement, how grassroots momentum can be transformed into sustained civic action, and why early organizing and early investment matter more than ever. Andrew also offers candid insights on Democratic strategy in conservative-leaning states, the growing possibility of a wave election, and what it will take to flip the House—and potentially the Senate—in 2026.

If you’re looking for a grounded, strategic, and energizing discussion about organizing, coalition-building, and reclaiming democracy one district at a time, this episode delivers.

Transcript

SPEAKER_02 0:00

Welcome to the Blue Dot, Northern Kentucky's premier political podcast. Brought to you by the Kent County Democratic Executive Committee. Welcome back to the Blue Dot Podcast, where we explore growing the Blue Dot in our own backyard. All of those pockets of progress seen in Northern Kentucky across the bluegrass and beyond. So growing the blue dot isn't just a buzz phrase, it's organizing, strategy, and building a ground game that can actually move the needle. And we're here to talk about it. Thanks for joining. I'm Natalie McDonald.

SPEAKER_01 0:30

And I'm Brian Cale, and today we're joined by someone who knows that ground game better than almost anyone. Andrew Grossman is a veteran strategist and a recognized leader in progressive politics and strategy, and notably served as the director of the Democratic National Convention Platform Committee for the 2012, 2016, and 2020 cycles.

SPEAKER_02 0:52

Yes, and his resume includes serving as the National Field Director and later the Executive Director of the Democratic Senatorial Campaign Committee, otherwise known as the DSCC, early in the 2000s. Andrew was also a key liaison for the Obama White House during the push for the Affordable Care Act. And today he is joining us to talk about what initiatives he's up to for the 2026 midterm election.

SPEAKER_00 1:18

Thank you for having me. I'm excited to be with you. Today I want to introduce Battleground Alliance to uh you and your listeners. Kentucky play is gonna play a key role on the electoral map in the United States in 2026 uh in the Kentucky Sixth District. So Battleground Alliance is a key part of the campaign to win control of the House of Representatives, and our road leads through uh through Kentucky.

SPEAKER_01 1:41

Yeah, that's you know, that's exactly obviously you want to key in on that uh sixth congressional district in Kentucky. And uh could you give us just a little bit of background on yourself and then also kind of the general strategy and background and founding of Battleground Alliance and uh what you guys have been up to, and and then we can drill down into how uh we can hopefully help uh win that sixth congressional district.

SPEAKER_00 2:04

So as you just uh as you noted, I'm a longtime gray-haired political uh uh organizer here. Uh I've been doing this for about almost for four decades now. This year, so over the course of my work, I've worked on um a range of different things from individual candidate campaigns throughout the country. I worked, as you mentioned, for the Democratic Senate Campaign Committee. I ran an organization called Walmart Watch for a couple of years, uh, took on the world's biggest corporation uh to be a better corporate citizen. We and I I'm a political consultant. I live near Hartford, Connecticut. Uh I have four adult children and um and have recently turned to the House of Representatives as a place where I like I've been enjoying working. The uh Battleground Alliance is um uh is the independent side, and I can explain that to listeners, independent side field organization whose job is to help turn out the voters who will make the difference for the Democratic candidates as we seek the lever that we need to win the House of Representatives to keep Donald Trump in check. Uh, and that that's the House. The House is our best lever. So this idea of Battleground Alliance on the again in the independent side, meaning we will not coordinate with candidates, we don't speak with candidates, we can't take direction from the candidates, we raise money under different rules from the candidates. Um, but and so we are kind of uh uh sectioned off. And uh the way we um we build independent field operations are uh currently I'm very excited is when we talk about the Kentucky Sixth District. We've already gotten started in in the 6th district with a couple of different uh uh uh experiments and partnerships based on the No Kings rally recently in Lexington. Um so we're really excited to kind of like dig in with people in Kentucky and on how to win that district. So Battleground Alliance was modeled after Battleground New York and Battleground California. In 2022, the Democrats lost well uh all the close races in New York and California, where they're not supposed to lose the close races, right? And um uh in New York, they lost five out of the six races that were decided by less than two points. So in 2024, we flipped that. We built a strong field operation in these battleground districts around the New York suburbs and upstate New York, um, and uh and flipped five out of the six districts that the Republicans had won uh just two years earlier. Uh that idea, we're taking that nationally, where we want to build on the energy that's been created by the resistance to the authoritarian regime or to the um uh the bubbling up of energy around no kings. It's super exciting right now, and we think that we can build strong local field operations to help win back house races in key places around the country.

SPEAKER_01 4:53

Yeah, it's really interesting to be able to uh have something like I've got to be exciting for you to have something like No Kings and you know, hands off, just that whole real grassroots, you know, movement. And, you know, back in the good old days of protesting now, it's protesting's hot again, and be able to have that momentum and that interest and build off of that with what you're doing.

SPEAKER_00 5:15

You know, and I'm a I'm a history buff. I love the allure of the United States. 250th anniversary of the United States to me uh has such a strong appeal because I was there for the bicentennial when we when all as little kids dressed up in with tri with tri-cornered hats and marched down the road with five and drum cores. And um, and so when I think about how important this is and the core idea that we do not have any, that we have a constitution that is meant to protect people and we and to promote people's prosperity and the right to find happiness, these are the American ideals and there are no kings involved. And so this energy that that has been uh that people have been building and have really creating and is now spinning into a place where it's very powerful. Um and it's powerful not just in the typical what you know people think of as the democratic cities or the democratic of the blue states, but it's powerful across the country in in in where anyone where who cares about our country and about our values is looking for a way to get activated, no king speaks to them. I think it's a very powerful idea. I'm very proud of the people who came up with the idea, and I hope that they keep building. We have three more years of Donald Trump.

SPEAKER_01 6:31

Yeah, please. Well, let's hope it's Donald Trump under the thumb of a uh Democratic House of uh representatives and even a democratic Senate. And then it's then it might be uh a somewhat, maybe a little bit more enjoyable three years. We might actually be getting somewhere.

unknown 6:47

Yep.

SPEAKER_02 6:47

Yeah, and I I like how you said that you're looking at some of these states, especially in New York, where the I remember when all of those those house districts went down by small margins, and then you flip them back. And looking at, I think you have 37 Republican-held house seats that you're that you're targeting, is that right?

SPEAKER_00 7:06

Currently. And that list may expand as the wave begins to build. You know, if you remember a year ago, we were all crying in our coffee at Democrats and worried and deeply paralyzed with both fear and kind of like a really uh our soul searching. And now there's a a new spirit and there's an energy. And so the I think the question is the is not whether we're we're we're gonna have a wave election, just like we've had for each of the midterm elections going back to 2006. But um, and and uh and when you think about a wave, think about it's not about how high it crests like uh a surfer on top of some beautiful beach in Hawaii, but rather how far it goes up the beach at the last little part when you're like a little kid trying to avoid the wave at uh the little bit of water on a on a long beautiful beach. And so the wave election as a reaction to President Trump's overreach, it's just like his total chaos and the harm that he's causing to regular people with tariffs and with the health care cuts. Um the uh I think that the uh the people are energized and ready to kind of tackle these, the the house has the lever to stop him.

SPEAKER_02 8:15

One of the questions I was gonna ask you well later was, you know, I'm sitting currently in Kentucky's fourth, which is not on your target list, but you just said there could be more. And I'm a firm believer that all seats are in play for November. I I truly believe that they are. And I don't know if you could talk a little bit about perhaps not only just for the fourth and the sixth here in Kentucky, but other places where maybe an alliance, and you said that helps build that momentum. Is that something that you're looking at to kind of build alliances in different states and kind of like working together with these different districts? Is it is it just money? Is it boots on the ground? Is is it a little bit of everything?

SPEAKER_00 8:50

It's a little bit of everything. Our goal is to win the House of Representatives. And so Battleground Alliance serves in a couple of functions. First is as a coordinator to bring people together around the races that are winnable and how you win those races. So, and there are many different people who want to win that in the House of Representatives. They've made the same analysis that I have that we need a lever to stop Donald Trump and the House is the best lever that we can get. So the uh so the coordinating role is so central. Second, we're an aligner. We're we need to, because all of the organizations and advocates, individuals who are energized, all are looking for a way that they can help win the House of Representatives. We're here to provide some of that guidance and answer and answer some of the questions about how. We don't want people tripping all over themselves. We want the candidates to prosper and to tell their own stories, but we are so we're an aligner as well. And then our our theory of the case is to work with local organization wherever we can. We want to build for the long haul, not just for this year's election win. We want to do both at the same time. So we our goal is to work with local organization in every instance in each place and and build out from the community first and then fill gaps where we need to with kind of uh like if money helps solve the problem, uh, then we'll we'll hopefully be there with money to help solve the problem.

SPEAKER_01 10:17

Yeah, that's what uh uh you mentioned the topic right there, the kind of like in it for the long run, you know, you're building, you know, you're building a foundation. It's not like we're just trying to get something in 2026 and then go away. And obviously, that ability to form a coalition and you have all these individual groups with you know what they've been focused on, the momentum they have and the base and the support that they have and pulling all that together, then you can help them get there, maybe a little of train the trainer kind of thing, show them the way, and then they can continue on and grow from that and build off of that for the long run. Is that the strength of the coalition versus you know a single organization that just can't be everywhere at once?

SPEAKER_00 10:57

You know, I think that there are so many people who are doing interesting and smart work around political organizing, around electoral work, around educating their neighbors and their friends and their community around issues that are important to all of us. And we want people who who uh want to do all of those things to we want to be helpful to them in whatever way they need to be helped, they need to be helped. I wouldn't, I don't want to, I want to make sure that we stress the partnership, not that we have some secret sauce that is special beyond, you know, because it's all of us are trying to get smart, smart to talented people are trying to do something together, and uh nobody has a monopoly on smart ideas um or or approach. So some places we may be additive because we have uh we we have money to work with from national sources who are also trying to win the house. Uh in other instances, it may be because we have a really good idea around how somebody can create solve a volunteer problem or can tackle a make sure that they're on message when they're when they're talking to voters about a healthcare so that they're most persuasive with people. How we show up is going to be a little bit different in each place. We're trying to like kind of love each place the way it needs to be loved and to be worked with so that people who are on the ground and live in place can be there again in 2028 and in 2030 and in 2032 for each election and grow success and build power so that we can uh we can change the country.

SPEAKER_02 12:28

Yeah, and I want to applaud what you're doing because we are a blue knot in a red state. As you know, we have a supermajority in our legislature, but we have a very popular governor with Governor Bashir. And I think a lot of it comes down to visibility and letting people know that Democrats are out there. So having organizations like you're and doing the work that you're doing in these small pockets, letting people know we're here, getting out that vote is really, really important. And I I feel like there's a lot of voter apathy, especially here in Kentucky for for Democrats who feel like, oh, we have the supermajority. What can I do? But then on the flip side, Governor Bashir won in my precinct by two votes. So I I think they're probably my votes. But uh, but but the point is it's getting it's getting people out there, it's getting people fired up, letting them know where Democrats are.

SPEAKER_00 13:16

Our most exciting initiative, we're we're trying a little test right now. The um the I, as we talked about, this energy that's been created around No Kings has resulted in thousands of people coming to events and showing up at rallies to express themselves, to be part of a community, to feel like they're part of something bigger than themselves. And that and that energy is just like so I I I love going up to my I live uh I work uh just a couple of blocks away from the Connecticut State Capitol, uh, and I loved walking out of my office that Saturday morning and joining the crowd for No Kings a couple of weeks ago. So what we're doing is to uh we we working with local partners in a couple of places around the country, including in the Kentucky 6th District, we tried to, we're trying a little effort that it might sound like it's fundamental to political organizing, but to some degree there's a little bit of a lost art around how to organize people. We're testing to see if people who come out to the rally, can we go get them to go and do appear at a politicians town hall meeting or to do a protest, or can we get people to go and volunteer on May 2nd? We're doing a national volunteer canvas day. And so we we're calling it the March to Organize, starting on on March 28th with the No Kings event. We're asking people, working with local organizational partners around the country, to bring people who said yes, I'll volunteer on No Kings on March 28th to do a couple of different actions prior to May 2nd and then wrap up with a door-to-door canvas on May 2nd in each of their own communities. So um in uh and and that initiative, we're in midstream, and it's something that like it sounds so fundamental, right? That we would uh that that's something you'd be able to do, but no one really has figured out yet how to turn that energy into action uh and to make it propulsive. And um, and and so we're we're trying doing some tests around the country. Our partners in in the 6th district are a group called Black and the Revolution Kentucky. Um and uh we'll be able to I'd love I look forward to reporting back to you about the results after as we go. Activities like this are happening all across the United States. So you're part of you're a blue dot, but you're one of so many blue dots all across the the country who are doing uh who are trying. Very exciting.

SPEAKER_02 15:44

I love that. Take take that no kings energy and turn that into further action. I love it. And I think if we if anybody can find out how to harness that, game over.

SPEAKER_00 15:55

Yep. That's exactly right. And you know, this is the case with the midterm elections. This year is the Democratic, we're we're going to have the wave election at our back, which makes the races in places like Kentucky 6, which President Trump won by a lot. It makes races manageable, and we think that we races where we can pick up and win seats for the House of Representatives to give the Democrats the majority.

SPEAKER_01 16:15

Yeah, I love the innovation and the flexibility. Going back to No Kings again, I know we're kind of beating that to death, but it's just, I mean, it's so inspiring. It's been so successful. You know, I love seeing Ezra and Leah on all the talk shows and everything, talking about what's coming next, what's coming next. And I'm always in the background of my mind going, did they have this plan? They have one great vision, everything's going to plan, or did they go, crap, that really works. So now let's do this, or how about that? You know, like some of the boycotts or, you know, some things like that. They're just kind of starting to build off like what would work, harnessing that energy they're seeing out in the field. It sounds like, you know, it's kind of the what you do in in the same way. You're you're kind of like seeing what works and and seeing what each individual organization, geographical area, cultural, you know, area, whatever requires, and just tweaking as you go along to figure out what works the best. And then building off of those, you know, the the best practices that you learn as you go along, I guess.

SPEAKER_00 17:13

That's right. And you know, I think there's two things. First is it's the time we're in, especially for our colleagues at No Kings. They are they are experimenting. They're they are moving with the momentum that they've they're start their that they've created, and now it's they're trying to, you know, they're always just a step ahead of it, or they're riding that momentum a little bit. And they are so and I think that the moment we're in calls for that because we haven't been in a time where the president of the United States does what the president of the United States does today. This is not normal.

unknown 17:49

Right.

SPEAKER_00 17:49

And I so I'm very sad for I as a father of people in their 20s that the is the president that they've known, and this is normal to too many people. But I think that we have a responsibility to experiment, to promote smart people who are trying to work in their own community to push back or to take over or to build power so that we can not only defeat this attack on our country uh from our own internal uh challenge that we're having, uh, but also to uh to help create the new, like what this should look like going forward, because there's always going forward. We are moving forward, you know, and we need to we need to create the United States that we want. So now fosters is the moment for experimentation in the way we do our work.

SPEAKER_02 18:40

Well, since we have a seasoned strategist with you on, I'm gonna take advantage of asking you a couple questions. Uh, the first one is we're moving into obviously our we're we're setting our sights on flipping the house. What are what do you think our biggest barrier is there? And my second question to you would be how can we win the Senate? Is the Senate in play? Could you make a prediction for that?

SPEAKER_00 19:02

Well, as you noted earlier, I grew up in the Senate. I worked at the Democratic Senate Campaign Committee for five years and learned that maybe the best group of people I've ever worked with, the smartest and most talented professionals. First on the the House, I'm sorry, so the on the Senate, I think for the first time in a long time, I'm even becoming a believer that the Democrats have a path to the Senate. It's still awfully hard. You know, I would I would like to think that the Democrats could win everywhere and uh that all 435 seats are up for grab. I I do deeply believe that we should have a candidate everywhere and in every race. Our colleagues that run for something and and uh contest every race are really doing incredible work. And I hope people sign up to run for offices where they live. But the truth of the matter is we won't win the Wyoming House of Representatives race, where if you look at the president's the president's approval rating is 6535, uh, which is upside down for most of the rest of the country. And so the the I think the key for the part one is the these are conservative places, and we have to be respectful of what people think. You know, the uh a great Bard once said, if you want to make you want people to follow you, you have to go to where they are and bring them with you to where you want them to go. And that's really about the politics of creative winning in places that are conservative for Democrats when the people don't like Democrats that much in in many of these places. I think that's something that we have to grapple with. And we have to do more than just be the anti-Trump party to win in these places. And I think that that's something that we're we're working through. As these races become the Senate now looks very much like it's in play for the first time, and that's pretty significant. I think a lot of that is about Donald Trump's total mismanagement of the U.S. economy, his authoritarian instincts that we need to push back on and a general chaos under which he operates. But we well, but we do we have this opportunity, but now we have to figure out how to take it in a way that is sensitive to the fact that these are conservative places that the Democrats would win races in. Same with for the House of Representatives to some degree. The battleground is the battleground for a real reason. And if you break down the map or across the country of where the battleground is in 2026, you're talking about there's a couple of races in Pennsylvania, and there's a couple of races in Michigan, and there's a couple of races in Wisconsin and in Arizona and in North Carolina, all the same places where there are presidential, the presidential swing states, and also the states where there are Senate swings. These are Senate swing states too. And so there's a great continuity about our politics for the House, just like there is for Senate and for and for president. But there's also all the individually, there's uh all this great opportunity elsewhere, too. In Iowa this year, for the first time in a really long time, the Democrats have an incredible opportunity to pick up three of the House seats. In Ohio, there's three Democratic seats that the Democrats could go get. In in Kentucky, the Kentucky 6th District, in New Jersey, New Jersey 7. We're looking pretty good either way. Redistricting passes in Virginia or doesn't pass in Virginia. There's probably going to be two pickups in Virginia that we can do. And even in Florida, there's a couple of districts that are ripped for the taking. And so the for the House of Representatives, the part of the key is to first, if any of your listeners are active Democratic Party donors, now's the time to give. Early money matters. So give now. Whether you give to Battle, you support Battleground Alliance, please call me. But if you uh but but if you choose to give to a candidate or to a local organization, give now. It's it's better. Don't wait till October when you're really excited. Now's the time to act. The second is everybody needs to kind of this idea that we have to win. This isn't actually a like to have. We we have to win.

SPEAKER_02 22:48

Absolutely.

SPEAKER_00 22:49

And when you think about have to and what that included in that, and when you make that analysis, the next logical thing is then coordinate and to align. Let your institutional ego take a back seat, even as your institutional needs might be important. And so for Battleground Alliance, what that means is that we are trying to promote, like, kind of like how do we act in an eagleist way for the greater good in helping win the House of Representatives with the Democrats so that we can get this lever to stop Donald Trump. And so the organizations are not as important as our cause. And uh, I think that that's getting everybody aligned around how important victory is is really critical and something that we have to do for all of the next 200 days as we approach election day.

SPEAKER_02 23:36

You gave me hope. You give me hope. It's fantastic.

SPEAKER_01 23:38

That's great information. Yeah, I guess, and you don't want to bet on this or hope for this or put any uh weight on it, but I feel like in 26 midterms, a lot of, you know, independents are hopefully gonna swing Democratic. And obviously, we got the Democratic vote. I think Democrats are gonna come out hard and heavy. Everybody I've talked to, people who are not interested in politics, are highly motivated.

SPEAKER_00 24:03

Yeah.

SPEAKER_01 24:03

In our, you know, in our social groups. But also I wonder just how many Republicans are gonna be like, I can't vote for Democrats, so I'm just not gonna vote. And we may suffer from the lack of, you know, votes from uh the Republican side, which may actually be maybe an advantage for us or help us.

SPEAKER_00 24:18

Well, I think that there's a couple of things here that probably help us with the not only those Republican voters, but there's a truth here, which is if you uh a pollster would tell you it uh it ain't polled, are you more likely to vote in 2026? Are you more motivated to vote in 2026 than you normally would be? The Democrats are off the charts and the Republicans are down here. And that shows up in the special elections in 2025. Starting with the Wisconsin Supreme Court election last year, Democrats voted at 70% and the Republicans voted at around 55%. In the New Jersey governor's race and the Virginia governor's race, Democratic turnout was was so high and uh Republican turnout was low. The energy is with Democrats who understand what's at stake. And this is not about the parties or the organizations or anything having to do in Washington. People understand what's at stake and they're turning out to vote. And that's happened across the country. It's what makes it possible for us to maybe win in Kentucky 6, which if Andy Barr had been running for re-election and if Donald Trump was as popular as he was before, everybody would have written off. But but the but the opportunity is here, and everything that that points to the wave election points to places like the Lexington, Kentucky. You love it.

SPEAKER_02 25:45

And you talked a little bit about, hey, if people uh want to get involved, they can donate, start donating now early. But how else can our listeners learn more about Battle Battleground Alliance and and how to get involved? Are there are like if we go to Fayette, it's Fayette County in Lexington, are there places there where they can volunteer, or how is it structured?

SPEAKER_00 26:03

So as you as we talked about, we're running through local organization all over the country. So uh at the moment, our first two organizations, Revolution Kentucky and Black, are both our local partners. We'll be expanding that over the course of the spring and summer, uh, working with different local partners. And so stay tuned. People can come to us at BattlegroundAlliance.org to get more information and to leave us their name if they're interested in getting in being involved. Uh, it's also a place where people can contribute. And we'll be uh in neighborhoods soon with uh with uh uh and looking forward to tapping into the energy with uh with people on the ground.

SPEAKER_01 26:40

That sounds great. Well, Andrew, um, we cover everything you wanted to cover. Anything you wanted to toss in here at the end. Uh you gave us a lot of information and as uh Natalie said, a lot of hope. I'll take that hopium anytime I can get it.

SPEAKER_00 26:55

Well, I guess I want to just say as a as a guy sitting here in in central Connecticut, uh, we knew about uh Matt Bevan before you guys did. And then I wish you had known. And then uh, of course, I I also had the uh the your governor gave a great speech at the Connecticut uh Democrats annual dinner last year, uh, and uh I'm excited that he is on the national stage uh as we all are. So uh that Connecticut-Kentucky connection is strong, and I I hope that we can be victorious together.

SPEAKER_01 27:23

Sounds great. Well, thank you so much for joining us, Andrew. We really appreciate it. And thanks for everything you're doing.

SPEAKER_02 27:30

You know where to find us. So if you need any support here in Kentucky, if if the fourth starts to come uh on your radar, let us know. But we're here for it. We're here to help and support everybody out there.

SPEAKER_01 27:41

Yes, things progress, and you got a good point in time where you'd you would like to come back or we'd like to have you back on to kind of get a progress report down the road here a little bit.

SPEAKER_00 27:51

Okay, good. I appreciate that very much. Uh so we'll be keeping touch and I look forward to continuing to listen. When um when we get past the primary and you have the candidates from the sixth district on, whoever wins the primary, I I will be sure to tune in.

SPEAKER_02 28:06

We'll give you a heads up.

SPEAKER_01 28:07

Thank you very much. We appreciate it.

SPEAKER_02 28:08

Thanks for watching.

SPEAKER_00 28:09

Thanks for watching. All right, thank you. Bye now.

SPEAKER_02 28:11

Bye-bye. Thanks so much for joining that great conversation about strategy for 2026. And don't forget, you can join the conversation at our Facebook and Instagram pages or at BlueDopodcast.com. And if you like listening to the podcast, consider donating to help fund it, which you can do by clicking on the donate link at BlueDopodcast.com. Until next time, stay curious, keep facts and focus, never stop fighting for what matters. Beat that, everybody.