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A Venture Approach to Politics
Democrats must take more risks and compete in right-of-center districts to save our democracy. Ben Samuels dives into his experience running to flip a winnable GOP-held seat in Missouri.
Democrats will spend $5,000,000,000 this cycle — but they lack competitive candidates in a dozen flippable swing seats. Below is an interview with a talented candidate who invested in this type of district — a former Republican who took a calculated risk in the face of redistricting uncertainty. While his personal investment and $1 million raised did not flip a seat this cycle, it represents the type of venture sorely needed given the increasing value of adding a single competitive seat to the map.
But first, make sure to read a deep-dive addressing this challenge from David Scharfenberg at The Boston Globe. He traveled to Michigan’s fourth congressional district, highlighted in our “Conceding Democracy” analysis on underfunded potential swing districts, to see the tangible effects of a strange reality: there are dozens of organizations and talented leaders working on candidate recruitment and support, but no single person is dedicated to (or responsible for) ensuring a competitive candidate emerges from MI-04. The exploding value of one US House seat and importance of candidate quality demand at least a couple full-time staffers in each potential swing district.
How could Democrats spend $5 billion this cycle but lack competitive candidates in a dozen potentially winnable House districts?
Politics has changed over the last two decades, with 3x as much spending going toward half as many competitive elections. But the political industry has not changed and is mostly spending money in the same ways (despite the fact that there’s much more money and way fewer places to invest it).
Competing in “light-red” districts requires long-term investment and a risk tolerance that is anathema to the structure of political parties and many aligned interest groups.
For moderates and democracy reformers, these missed opportunities are magnified by the potential secondary effects of investing more in delivering quality candidates in “light-red” districts. As Scharfenberg writes in the Globe:
“Defeating election deniers like Giménez and Huizenga would strike an immediate blow for American democracy. It would mean fewer norm-corroding voices in the halls of power. But it would serve a broader democratic purpose, too.
The Democrats most likely to succeed in light-red America are not conventional Democrats. They’re ex-military. Or small-business owners. Maybe they part ways with the party on a social issue or two. The Democratic Party could use more of these voices. So could the country.
We are in the midst of a dangerous clash between left and right. And the best way to tamp it down is to rebuild the political center — to reconstruct the moderate factions that were once substantial parts of our two major parties.
A Republican Party still in thrall of Trump seems unlikely to lead that effort. But if Democrats build a moderate wing in red-state America, if they start to win more races there, then Republicans will be forced to respond. They will have to put up their own slate of moderates. They will have to talk more about compromise and civility. And if we get a few more politicians talking like that, well, we might have the beginnings of a different kind of politics.”
Achieving this future relies on changing the political marketplace by taking more strategic risks: “A sort of venture capitalist’s approach to politics — identifying and betting on a bunch of long shots with the expectation that many will fail but a few will produce spectacular returns.”
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A Candidate’s Guide to Winning the Middle
Ben Samuels knows what it looks like to take a “venture capitalist’s approach to politics” in order to win light red districts. Earlier this cycle, Ben ran a big-tent campaign against democracy-undermining GOP incumbent Ann Wagner in Missouri’s second congressional district, in which he focused on bipartisanship and common-sense solutions to mainstream issues. (That is, until the Missouri state legislature drew his home out of the district and altered the new lines to heavily favor the incumbent Republican.)
In running against a well-established GOP incumbent in a right-of-center district, Ben took a calculated risk of the type that Democrats need more of. In the aggregate, we must invest more in recruiting and supporting candidates like Ben running in districts like his.
Since ending his campaign, Samuels has joined The Welcome Party’s team as a Senior Advisor. We spoke with Samuels this week about his campaign, what he learned from reaching out to swing voters in his center-right district, and what practitioners looking to win the middle can take away from his experience on the front lines.
The following interview has been edited for clarity and length.
The Welcome Party: Tell us a bit about your background and why you ran for office.
Ben Samuels: I moved into government and policy in large part because of Donald Trump’s election. There was a clear sense at the start of the Trump era that the world was shifting in the wrong direction, and I felt some sense of duty or obligation to try to do something about it.
I left the private sector (I had been working for Mastercard at the time) and ended up working for Rahm Emanuel, the Democratic mayor of Chicago, through the end of his term. After that, I worked for Charlie Baker, the Republican governor of Massachusetts, doing economic development and climate transportation work.
But even then I really didn’t think seriously about running for office. What really inspired me to run was the culmination of everything we had seen over the last two years: denying the results of free and fair elections has become table stakes for the Republican Party.
I had moved back to St. Louis at the beginning of the pandemic to be closer to family. We’ve got a Republican incumbent here named Ann Wagner who was elected as a moderate when she first ran for office ten years ago but has since tacked very hard to the right with the rest of her party. Ann has done a good job positioning herself and talking like a moderate—but the way she votes and acts with respect to democracy is as dangerous as anyone else in the GOP.
I feel strongly that we have to try to win these sorts of elections against established Republican incumbents who are actively and willingly subverting democracy. Mitt Romney won the old version of this district by double digits in 2012, but by 2020 it had become a purple district where Trump won by all of 115 votes out of about 750,000 people. So there was a real opportunity here—in a Republican-held district that was breaking toward Democrats—for the right kind of candidate with the right message to flip the seat.
That’s when I started thinking things through more seriously and began having conversations with people here to understand what running for office might look like.
Why did you end up dropping out?
Going into the race, I knew that redistricting was a risk, so before I jumped in, I talked with a bunch of state legislators (including Republicans) to try to get a feel for what that might mean for my district.
The consensus was that the district would get a little bit harder but largely stay the same. The reason for that was because the incumbent, Ann Wagner, had made herself vulnerable to a primary from the right by positioning herself as a reasonably moderate Republican. For that reason, in the interest of keeping her seat, she and the Republican establishment did not want the district to get too much harder.
Sure enough, the Missouri House passed a new Congressional map and it was exactly what we expected it to be. But things got more challenging in the state Senate. Without getting into the details, the Senate’s Conservative Caucus — which was a splinter group from the Republican Caucus — filibustered their own party for about five months and held out until they got a map that made the district unwinnable for a Democrat this cycle. And just for good measure, they drew my house out of the new district by about a block.
At that point, I was no longer living in the district and found myself carved out of every compromise map. Each new map that followed was drawing my house out by either half a block, a block, or sometimes as many as two blocks. It’s about 10% flattering and 90% infuriating to personally be the target of the state legislature like that.
But having been explicitly drawn out of the district — and with the newly-drawn district this time around having been gerrymandered into being unwinnably hard — I figured there were better ways to spend my time and resources than running in a race I knew I couldn’t win.
What have you been doing since then?
I’ve been doing what I can to help other candidates who share my sensibilities who are running in tough, competitive races around the country and working to support a pro-democracy Democratic majority from the sidelines rather than as a candidate this time around.
Speaking of candidates who have run in competitive races, who are the people in politics who most inspired you as a candidate?
I’m inspired by the candidates who have done a good job appealing to voters on both sides of the aisle and demonstrating that a bipartisan message can provide a path to victory in challenging districts.
I think we have to look to candidates like Jared Golden in Maine, who won pretty convincingly in a district that voted heavily for Donald Trump. Golden was able to do that by talking about the issues that mattered to voters locally and distancing himself from a lot of the Democratic Party’s national brand. He’s done a good job representing the district, and his voters know that.
In Missouri, I think of Jason Kander, who lost here in 2016 but did so only by three points the same year that Hillary Clinton lost by the state 19. Our former Senator Claire McCaskill is the same way: she was winning in Missouri well after it had become a more solidly Republican place. She ran a strong and competitive race against Josh Hawley in 2018 — and she did it by running on her bipartisan credentials and as someone who doesn’t toe the party line. She ultimately lost, but she lost by a lot less than the state’s partisan lean would’ve suggested.
Those are some of my personal favorites, but there are a bunch of other candidates across the country and throughout the midwest who have done a similarly good job.
You were running in a WelcomePAC target district — a Republican-held seat where Trump won in 2020, albeit not by much. What was your approach to running in this kind of seat?
I was very explicit about the fact that I had most recently worked for a Republican, which I think was unique among Democrats running for the House across the country. I was also quick to highlight that I’d worked for a Democrat, a Republican, and a private sector company (Mastercard) that’s one of the biggest employers in my district.
I really tried to demonstrate that I’m not someone who’s going to be a party line voter. I have a bipartisan background: that’s who I am and how I see the world. That’s compelling to voters in a district where Romney won ten years ago — and where Trump and Biden effectively tied just two years ago.
That means there’s a large number of Romney-to-Biden voters and a decent number of Obama-to-Trump voters, too. There are a lot of people who are not simply party line voters — people who have voted for candidates from both parties in the very recent past. They split their tickets between Donald Trump and Jason Kander in 2016 and Ann Wagner and Claire McCaskill in 2018. So I cannot highlight enough how big of a deal it was to play up my bipartisan background.
It’s important to talk about stuff happening nationally that’s popular, but I think you win in districts like mine by talking about stuff that matters locally. For example, crime is an issue everywhere in the country, but no place more than in St. Louis. The city of St. Louis has the highest murder rate of any city in the United States. People don't feel safe in a lot of parts of the metro area. Particularly as Democrats in an environment where a lot of voters don’t trust us on this issue, we have to go out of our way to demonstrate that we care about crime and public safety, that we’re going to do what it takes to support police and the sorts of institutions that keep our communities safe.
Additionally, St. Louis is 47th out of the 50 largest metro areas in the United States when it comes to economic growth rate. There are very few major cities and metro areas that are growing more slowly than St. Louis. The manifestation of that is not just the perception that jobs are leaving and that the region is losing some of its prestige, but that people’s kids are heading out and not coming back. Not only had I worked for a Republican in economic development, but it was important for me to be able to tell people whose kids had left and had no plans of coming home “I’m a younger candidate who’s moved back here, I know what it takes to get people to move here.” We have to run against the status quo in a place like St. Louis where it’s really not working.
I also think it’s easy to miss that voters are not monoliths and party affiliation is not monolithic. For example, on the hot-button issue of abortion, I went to a Democratic township meeting in a very Catholic part of my district and every single person at this meeting would have self-identified as pro-life. There were also very Republican parts of the district, like Chesterfield out West, where a big chunk of the voters would identify as pro-choice. That’s just one example, but there are plenty of issues where people don’t cleanly break with one party or another.
It’s well known that the Democratic Party’s far-left national image can be alienating to independent and right-of-center swing voters. How did you work to overcome the limitations of the Democratic brand?
If you get everyone who voted for Jason Kander or Claire McCaskill to vote for you, you’d win my district. A significant number of these people have generally voted for Republicans but have, in certain cases, voted for Democrats. Add in the Obama-Trump switchers, and there’s just a huge universe of voters who have voted for both a Democrat and a Republican at some point in the recent past.
But a lot of people here are turned off by the Democratic Party because of the perception that Democrats favor defunding the police, higher tax rates, policies that don’t do a lot to reduce crime, and policies that don’t drive economic growth. As a candidate, I went out of my way to play up my background working for a Republican in economic development and experience in entrepreneurship working for a startup that then got bought by Mastercard. In addition to that, it is important to voters in the middle that you’re not going to be a party line voter. A willingness among candidates to be independent and buck the party line is why a lot of these people have voted for Democrats in the first place, even if they would generally identify as an independent or Republican.
Finally, what should Democrats in deep blue enclaves take away from your experience reaching out to swing voters on the front lines of the battle for our democracy?
Not only are where you live and what kind of educational attainment you have the two biggest determinants for how you vote, but they’re also the biggest determinants of who you know. On both sides, that has led to an empathy gap where it is harder for people to understand how and why people vote for someone of the opposite party.
For all of the lack of understanding that people in cities have for how someone could ever vote for Donald Trump, people feel the exact same way in ex-urban and rural areas when it comes to how someone could vote for Clinton or Biden. That’s a very real perception out there — and it becomes especially real when you get to counties in Missouri that broke 85%-15% for Trump.
One of the unique privileges of running for office is you get to meet people everywhere and see that, fundamentally, people want the same thing. They may think, vote, and talk about an issue slightly differently, but everyone wants affordable healthcare, safer communities, and more prosperity and economic development. Sometimes, we disagree on how to get there — but even then by less than we think. We need to understand that people who don’t vote or talk like us aren’t as far away as we might think.
Running for office in a swing district gives you a unique vantage point for seeing that. Now more than ever, we just need more people who aren’t in the business of dividing.
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