Ben Wikler

President Trump is very unpopular right now. But polls show the Democratic Party is just as unpopular – if not more so. So what can the party do about it? But to answer that question, you first have to understand what the Democratic Party is. That is, mechanically, what is it? What powers does it have? When you call the Democratic Party, who picks up the phone? And how can that party, the official party, be reinvented for this era? Ben Wikler has a unique perspective on this question. He transformed the Democratic Party of Wisconsin into a fund-raising, door-knocking powerhouse when he served as chair from 2019 to 2025. And he’s shared some of his insights from winning elections in a swing state in his new book, “This Is The Plan: How to End America's Meltdown and Save Democracy.” In this conversation, we discuss Wikler’s vision for a reinvigorated party, as well as the kinds of changes he thinks Democrats need to embrace if they want to build a bigger tent and a national majority.

The Democratic Party’s rallying around Kamala Harris — the speed of it, the intensity, the joyfulness, the memes — has been head-spinning. Just a few weeks ago, she was widely seen in the party as a weak candidate and a risk to put on the top of the ticket. And while a lot of those concerns have dissipated, there’s one that still haunts a lot of Democrats: Can Harris win in Wisconsin? Democrats are still traumatized by Hillary Clinton’s loss in Wisconsin in 2016. It is a must-win state for both parties this year. And while Democrats have been on a fair winning streak in the state, they lost a Senate race there in 2022 — a race with some striking parallels to this election — which has made some Democrats uneasy. But Ben Wikler is unfazed. He’s chaired the Wisconsin Democratic Party since 2019 and knows what it takes for Democrats to win — and lose — in his state. In this conversation, he tells me what he learned from that loss two years ago, why he thinks Harris’s political profile will appeal to Wisconsin’s swing voters and how Trump’s selection of JD Vance as his running mate has changed the dynamics of the race in his state.