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? 

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Ben Wikler joins The Chuck ToddCast

01:00 Ben’s new book is “This Is The Plan”

01:15 What is the plan?

01:45 To get political change we need, we need to change the system

02:30 To secure free & fair elections, need to win at the state level

03:00 We need an end to the filibuster and Supreme Court reform

03:45 There’s no one office or candidate to get us out of this mess

05:45 We need to win the ring of power, then cast it into Mount Doom

06:15 When the right wins power, they immediately change systems

07:15 We keep having change elections, then not getting change

09:30 We’re in the greatest period of political instability in American history

12:30 Both party bases want to fight more than want to win

13:30 We’re so gerrymandered, people don’t really get a vote

15:00 Swing/Non voters have given up on the system itself

19:30 Are rebuilders or renovators going to win the argument?

20:00 FDR’s social security pitch was a big swing

22:30 Incrimentalism was the only way to pass Obamacare

23:15 The art of politics is values/vision, then figure out what can actually pass

24:15 A party should be able to change laws, then face the voters

25:30 Need to reform the Supreme Court to reform campaign finance laws

26:15 Advocate for term limits for Supreme Court justices in the book

26:45 Inequality is now worse than it was during the Gilded Age

28:00 Is Francesca Hong too “Madison” of a candidate for Wisconsin gov?

28:45 Hong has been traveling the state & listening for years

29:45 Wisconsin Dem gov primary has been topsy turvy

30:45 Tom Tiffany is an election denier & beatable candidate

32:00 Affordability is the central issue this election cycle

34:45 Why did “calming the waters” work for Tony Evers, but not Joe Biden?

35:30 Evers came out very strongly against Dobbs

36:15 You have to convince a majority of the public that government works

38:15 Trust is earned by doing what you say you’ll do, then highlighting it

39:45 Pandemic relief had a massive positive effect on lower income voters

40:15 Those programs stopped, and voters punished Dems for it

41:00 Child tax credit cut child poverty in half, great accomplishment for Dems

41:30 There was bipartisan support for extended tax credit, still didn’t get done

42:00 Filibuster is used to deprive the other side from getting a win

44:30 Politicians can lay out a succession plan, but voters get their say

46:00 Politicians are limited in setting out a succession plan

47:30 How big should the Democratic tent be? 

48:30 The coalition looks different in different states

50:00 Donald Trump has been the most successful GOP politician of this era

50:45 Every Republican politician looks to Trump as the model

51:15 Trump has created an army of “mini-mes”

53:00 What Ken Martin is doing right: Building state parties

55:45 Democrats don’t need a 50 state strategy, they need 50 state strategies

56:45 You build a local brand through your actions over time

57:30 When did you first think about running for office?

59:30 Support Tammy Baldwin’s bill to provide live Packers games

1:01:00 Most excited about Jordan Love in the upcoming season

1:02:15 Why wouldn’t you run for the senate?