Episode Details

Chuck Todd begins the episode with an examination of the election landscape starting with the California gubernatorial race and a demographic breakdown that indicates Democrats could perform very well in both 2025 and 2026.

Then, is joined by businessman Stephen Cloobeck, who discusses his candidacy for California governor as the "only non-traditional candidate" in the race. Cloobeck offers sharp criticism of the Harris/Walz presidential campaign, which he characterizes as "tone deaf," while proposing concrete solutions for California's most pressing issues. 

Cloobeck outlines his vision for a new department of "performance and results" to increase government accountability and presents his approach to addressing California's homelessness crisis. Drawing on lessons learned from his adopted father, former Senate Majority Leader Harry Reid, Cloobeck positions himself as a Democrat who understands business concerns, directly addressing why corporate leaders are "tempted" to leave California while asserting that "you can't buy an election" and pledging not to self-fund his campaign.

Chuck presses Cloobeck on whether Democrats need their own version of "Donald Trump," and what the party should learn from Trump's political approach. He also offers insight into his success in the timeshare industry, explaining how Marriott ultimately copied his business model and addressing whether AirBnB has undermined the traditional timeshare market. Chuck challenges Cloobeck about potential competition from other business figures like Rick Caruso and former governor Arnold Schwarzenegger, with Chuck speculating that by 2026, voters might be "burned out on bravado" after Trump's presidency.

Finally, Chuck digs into the mailbag of listeners’ questions in Ask Chuck and responds to questions about six year presidential terms, quirky personal preferences that lead to political preferences and whether it’s harder for him to land interviews with Republicans.

Timeline:

00:00 Introduction

00:30 The importance of the California gubernatorial race

01:15 Kloobeck intro

02:30 Kamala Harris preparing to run for governor in California?

03:45 Younger and infrequent voters were Trump’s “secret sauce”

05:00 Can a Democratic woman win the presidency?

06:30 Higher turnout is better for Republicans

08:15 Trends favor Democrats in non-presidential elections

09:30 Democrats became the “rules” party

11:15 Jared Golden not running for must-win Maine senate seat

12:30 Republicans are already writing off Virginia

13:30 Could New Jersey become a swing state?

14:30 Can the Trump coalition succeed without Trump on the ballot?

15:45 Could Senator Bill Cassidy retire for LSU chancellor job?

17:15 Stephen Cloobeck joins the Chuck ToddCast! 

18:30 Why is he the only non-traditional candidate running for CA governor? 

23:05 Are California's issues a governor issue or does it run deeper? 

26:05 What should Gavin Newsom have done differently? 

29:00 The Harris/Walz campaign was tone deaf 

30:25 What did Gray Davis get right as governor? 

31:55 Creating a department of "performance and results" 

33:30 Solution to California's homelessness problem 

35:00 Schwarzenegger was an outsider that ran into the bureaucracy 

39:30 What makes him a democrat and not an independent? 

41:55 Why are business leaders "tempted" to leave California? 

44:35 What he learned from his adopted father, Harry Reid 

46:15 Do we need a "Donald Trump" in the democratic party? 

48:00 What should the democratic party learn from Trump? 

48:45 You can't buy an election. Won't self fund his campaign. 

51:00 Why couldn't Trump start a casino in Nevada? 

53:20 Should people be skeptical of the timeshare industry? 

54:35 Has AirBnB killed the timeshare industry? 

58:00 Marriott copied h