Episode Details

Ben Wikler, the former Wisconsin Democratic Party chair and author of the new book This Is the Plan joins the Chuck Toddcast to argue that Democrats keep making the same category error: they keep winning change elections and then failing to deliver change, because they're trying to fix policy without first fixing the system that determines who gets to make policy. Wikler's framing is memorable and a little cheeky — you have to win the ring of power and then cast it into Mount Doom — but his point is serious. When the right wins power, it immediately restructures the system to entrench itself; Democrats win and then govern as though the rules are fixed. His plan runs through the state level, where free and fair elections are actually secured, and demands ending the filibuster and reforming the Supreme Court, including term limits for justices, because campaign finance reform is impossible without a Court willing to allow it. Wikler argues America is in the greatest period of political instability in its history, that inequality now exceeds the Gilded Age, that gerrymandering has left millions of people without a meaningful vote, and that both party bases increasingly want to fight more than they want to win — while swing and non-voters have simply given up on the system itself. He rejects the tired rebuilders-versus-renovators binary: FDR's Social Security pitch was a huge swing, incrementalism was the only path to Obamacare, and the actual art of politics is starting from values and vision and then figuring out what can pass.

The conversation gets specific about Wisconsin and about trust. Wikler pushes back on the idea that Francesca Hong is too "Madison" for a statewide race, notes she's spent years traveling and listening across the state, and calls Tom Tiffany an election denier who is genuinely beatable in a cycle where affordability is the central issue. He and Chuck work through the puzzle of why Tony Evers' calm, steady approach succeeded where Biden's didn't — Evers came out forcefully against Dobbs, and, more fundamentally, you have to convince a majority of voters that government can actually work, which means doing what you said you'd do and then relentlessly telling people you did it. Wikler points to pandemic relief as the cautionary tale: those programs dramatically improved life for lower-income voters, the child tax credit cut child poverty in half, and then it all expired and Democrats got punished for the loss rather than credited for the gain — with an extension that had bipartisan support dying anyway, because the filibuster exists largely to deprive the other side of a win. He credits Ken Martin for investing in state parties, argues Democrats don't need a 50-state strategy so much as fifty different state strategies since the coalition looks different everywhere, and concedes that Trump has been the most successful Republican of this era, spawning an army of mini-mes modeling themselves on him. And yes, Chuck asks the obvious question — why not run for Senate yourself? 

Thanks to the sponsors of The Chuck ToddCast:

Upgrade your everyday. Go to https://Quince.com/CHUCK for free shipping on your order and 365-day returns. 

Play ball and swing for the fences on FanDuel, an official partner of the MLB at https://FANDUEL.COM. 

For free and unbiased Medicare help, dial (980) 734-3985 to speak with my trusted partner, Chapter, or go to askchapter.org/chuck / *Paid Partnership

Chapter and its affiliates are not connected with or endorsed by any government entity or the federal Medicare program. Chapter Advisory, LLC represents Medicare Advantage HMO, PPO, and PFFS organizations and stand alone prescription drug plans that have a Medicare contra