Wisdom from Obama's Florida Man

I did this interview with Steve Schale more than a month ago. But I actually feel that it feels even more relevant today - when it seems more likely than not we’ll have elections in 2026, and our job will be to win them. Steve has spent his life in Florida Democratic politics, which means his political acumen is matched only by his capacity for suffering.

My biggest question for Steve is why Florida - which has experience all kinds of right-wing governance over the last four years - hasn’t seen the kind of backlash we’re hoping will happen against Trump nationally. But we also got into what Democrats do next, including what I thought was a pretty profound insight from Steve about the real danger (politically) of “woke.”

Below is an edited transcript. Personally, I kind of like this format - longer video plus shorter transcript - and I hope you do too, because I’d love include more of these in Word Salad. Either way please let me know!

DAVID

So you were Obama's Florida guy, and now you're still a Florida guy? But also, you were recently in Michigan? 

STEVE

I ran Florida in ‘08. I had the greatest job that any state director will ever have, which was this massive state in a campaign that wasn't really looking at Florida until late [in the election]. I didn't want to run Florida again [in ‘12]. So when [Obama] went back to the White House, I became the volunteer, the special envoy, to Florida. And then I got back into the re-election against my will in ‘12. 

In ‘12, I got to know Biden pretty well. When he was thinking about running in ‘16, Greg Schultz and I had talked. He didn't run, obviously, and I thought that career was over. I saw Biden in ‘18, and he's like, “I’m probably going to do this.” So I ended up running his first super PAC in 2020 and did a little bit in ‘24 [before] they went in a different direction. 

I ended up in Michigan because I've been concerned about the erosion of not necessarily the Obama coalition, but the working class coalition across ethics. I woke up the day after the ‘24 election and said, “I want to understand more of what’s happened.” I ended up in Michigan for that reason. 

DAVID

Let's talk about Florida. Trump Chief of Staff Susie Wiles is a Florida person. Trump is now a Florida person. So politically speaking, are we seeing Florida-fication of the United States, or is it a little more complicated than that? 

STEVE

It’s probably a little more complicated, but I don't know that it's a lot more complicated. I mean, I've known Susie. We were hacks together in Florida 25 years ago, so it's interesting to see her where she is now. 

DAVID

Interesting in the sense of “Impressed by how far she's risen,” or that you wouldn't have expected her to work for someone like Trump?

STEVE

No. I mean, listen, she's extremely talented. I've had nothing but respect for her over the years. We've worked together on some stuff. Back in the day, we worked against each other plenty of times. I think we have mutual respect. And part of what makes her unique is that she’s now sort of at that age where she's comfortable with all the stuff that she's done in her life. So she's not trying to prove anything to anybody else. She's a good manager. People that work for her really like working for her, she’s very loyal to her staff. And also, there’s a Susie Wiles way of running elections. I’ve tried to scream this as best as I could to the hard, non-SuperPAC side. Like, “I've been here. I've seen this. You're falling into her trap!” 

DAVID

So what is it? What’s the Susie wild way of running elections? 

STEVE

Susie really made her name in Rick Scott world, and Scott was like Trump in a lot of ways: a very flawed candidate. Most people thought it was unthinkable he could win. Some of their success was a function of the environment helping them, but they're smart enough to understand that your candidate has got massive problems. So rather than trying to fix those problems, you shine a light on your opponent in a way that makes your opponent seem just like you. So every insane thing you know that [Democratic] candidate has done, kind of makes [the Democratic] candidate equally unacceptable. And then turn the race into one thing. 

DAVID

“I suck, but the other guy also sucks.” So what’s the way to fight back against this? 

STEVE

The closest we ever got to beating them was in ‘14. We found you had to throw everything back in their face. In some ways, it was the old Obama model: any lie that sits more than 12 minutes is a fact. You have to turn it around as fast as you can. 

I remember that they ran an ad making some absurd claim. We actually just ran the ad back [saying] this is the lie. This guy’s a liar. I would have loved to do that with Trump, just turn it into a muddle. Do the same things to them as they do to us and force all these charges back into a muddle to get the race back on our own footing. 

DAVID

Florida was a reddish, purple state. Now it is not purple, to put it mildly. Florida has done a lot of very conservative things I’d assume people would hate, but there’s certainly no backlash that I’ve seen. Why? How have they been able to avoid that backlash?

STEVE

Obama was able to keep non-college, white, working class communities closer. He had more appeal in those communities. Florida has one of the highest non-college white populations. 

Our performance in Florida’s gotten worse with Hispanics. Florida's Hispanic population has always been more conservative. We have more Latin American, Central American, South American, Caribbean. They tend to be wealthier. The fastest growing population in Florida are Hispanics.

The other thing that’s about Florida is that our black population has always been way more diverse than the rest of the country. In most places, if you're black, you're African-American. In Florida, if you're black, there's a chance you're Caribbean or Haitian. It's always been a persuasion target, not as much of the base. 

You take these buckets of people, and as a party, we’re not don’t well with these voters in general. That national issue becomes magnified in Florida. What we saw in Florida with those populations starting to go south is ‘16 and ‘20. We saw that play out in a lot of states in ‘24. 

DAVID

Is there a sense that public opinion is tied to what politicians are doing? Or is that there’s really almost no limit to what Republicans can do from a policy or governance perspective and have to worry about losing elections? 

STEVE

The ability to communicate with voters is a problem here. Our brand here is terrible as a party. We've been just out-resourced in a lot of ways. Again, the coalition doesn't work. I have the view that the problems that my party faces nationally are just exacerbated in Florida. We have to fix some of those things if we want to be more competitive nationally. And if we do that, Florida is going to get better. 

DAVID

Recently, you were in Michigan. You wrote on your Substack about the mix of voters. Everything you said about the Democratic Party was deeply depressing. Want to restate that for the record and what to do about it? 

STEVE

I view these elections as a math question. After the election, I was curious about what happened in 2024. In my view, nothing specific in the last four years made 2024 happen. A lot of the coalition stuff we’ve seen began to degrade since [Obama] ran for re-election ‘20. Biden put a band-aid on that in ‘20, but in part due to the fact that people were just sick of Trump. There are nine states in the country that either party has won at least once since ‘12. In those nine states, we’ve lost ground in all but 50 of 767 counties. In terms of swing counties, Macomb County is one of the largest swing counties in Michigan from ‘12 to ‘24. The voters that we talked to up there, most of them voted for Obama. Half of them voted for Biden. All of them voted for Trump this time. 

There was just this frustration that the government doesn’t work here anymore. In their mind, Trump was [actually] doing shit, even if it was stuff they didn't necessarily love. They viewed Trump as a guy who is strong enough to use the pen to solve problems. They’re seeing action, and from us, they saw a government that wasn’t working. 

DAVID

That’s actually not what I would have taken away from reading your piece. I would have said you’re screaming at Democrats to stop being the party not for the median voter, caring more about marginalized people than them. 

STEVE

It goes back to your last question on the government not working. The woke stuff becomes a problem for us because they think that’s what we’re working on. Not that it’s a government that doesn’t work, but that that’s what we’re working on. 

DAVID

I see, like government’s priorities are misplaced. Is there a way to thread this needle? So voters feel they’re a priority but Democrats aren’t throwing marginalized people under the bus in order to convince other voters they care? 

STEVE

That’s why we’re the Democrats. We think everyone deserves a voice. But as the Chicago HQ always told me during the Obama campaign, our job is to win this election, and we focus on that. I think the hard thing for a lot of our Democratic friends is the reality that the only way you deal with this Trump stuff is at the ballot box. We can protest and boycott, but at the end of the day, we gotta win the house in 2026. 

In ‘26 we should recruit very broadly. Depending on what happens, the map could get very wide. 

DAVID

What’s the one thing you would like to see the Democrats do if you ran the circus? What would you like to see happening that isn’t happening?

STEVE

Listen, I believe you win elections by addition, not subtraction. For a while, we as a party have gotten so caught up in the analytics of groups, we’ve forgotten how to communicate to a breadth of America. 

What’s interesting is in a couple of years beyond the [‘28] election, in 2030 there’s going to be a new census. That new census is going to change the map in ways that will radically change elections. So for us to win the White House or congressional majorities, we have to start winning in places that we’re losing. We’ve got to start building a party that's focused on what that future reality looks like. And that means making places like Georgia and Arizona and North Carolina and maybe even places like Florida or Mississippi or Kansas more competitive for us going forward. 

If I had a magic ball, and somebody said, “Hey, here's 100 million dollars to go work on a project”, that’s the project I would work on — creating a better environment in these places. We have to expand.