Meet The Democratic "Donald Trump" Running For Governor Of California
05/21/25 • 87 min
1 Listener
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 his timeshare model
58:45 What would you say to Harris if she wanted help with the governor race?
1:02:00 Are you ready for the arrows coming your way
1:04:25 Did you have high expectations for Joe Biden?
1:07:15 If Rick Caruso jumps in, will you cannibalize each other's candidacies
1:10:35 Would Arnold Schwarzenegger be the front-runner if he ran?
1:11:35 By 2026 could voters be burned out on bravado by Trump
1:13:30 Chuck's thoughts on Stephen Kloobeck interview
1:14:45 Check out Chuck's interviews on Noosphere!
1:16:20 Ask Chuck
1:16:45 If congress was expanded, should the president get one 6 year term?
1:19:50 What odd voter personal preferences indicate their political preferences?
1:24:00 Do you find it harder to get interviews with Republicans?
(Timestamps may vary based on advertisements)
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 his timeshare model
58:45 What would you say to Harris if she wanted help with the governor race?
1:02:00 Are you ready for the arrows coming your way
1:04:25 Did you have high expectations for Joe Biden?
1:07:15 If Rick Caruso jumps in, will you cannibalize each other's candidacies
1:10:35 Would Arnold Schwarzenegger be the front-runner if he ran?
1:11:35 By 2026 could voters be burned out on bravado by Trump
1:13:30 Chuck's thoughts on Stephen Kloobeck interview
1:14:45 Check out Chuck's interviews on Noosphere!
1:16:20 Ask Chuck
1:16:45 If congress was expanded, should the president get one 6 year term?
1:19:50 What odd voter personal preferences indicate their political preferences?
1:24:00 Do you find it harder to get interviews with Republicans?
(Timestamps may vary based on advertisements)
Previous Episode
Trump Is "POISONING The Well" In Congress + Devastating Medicaid Cuts w/Ritchie Torres
Chuck Todd welcomes Congressman Ritchie Torres for a wide-ranging conversation that begins with a tour of New York's 15th district and the unique challenges of representing one of America's most diverse urban areas. Torres offers candid insights on governance, highlighting how term limits disadvantage legislators compared to lobbyists. The conversation shifts to the current political landscape, with Torres expressing deep concerns about President Trump's approach to his second term, arguing that Trump is "poisoning the well" for bipartisanship despite Biden's successful record of cross-party legislation. Torres delivers a stark warning that America is "planting the seed of its own decline" and characterizes the consequences of proposed GOP Medicaid cuts as "barbaric," particularly in light of the brewing long-term care crisis.
They weigh the merits of pragmatism versus idealism in American foreign policy and scrutinize Qatar's growing financial influence in American politics. Torres argues that "Republicans would impeach Joe Biden if he had accepted a plane" while addressing whether Democrats should adopt Trump's aggressive approach to wielding power. Torres acknowledges that Democrats "should have spoken out sooner about Biden's decline" and offers his vision for how the party can project strength moving forward.
They conclude with Torres addressing his political future—including speculation about mayoral and gubernatorial ambitions—before outlining his solutions for New York's housing crisis, crime concerns, and utility costs.
Timeline:
00:00 Introduction
00:50 Joe Biden diagnosed with aggressive form of cancer
02:00 Was Biden’s decline covered up, or just willful ignorance?
03:00 Robert Hur recording has supercharged the Biden story
06:45 Joe Biden couldn’t assure voters he was up to the job
08:30 Chris Murphy says it’s the Democrats fault that Trump was re-elected
11:45 Democrats need to do soul searching like they did with Bill Clinton
13:30 Clinton had to run against the party and its prior leadership
15:00 Democrats misread the 2020 election result
18:00 Democrats will take some blame for problems Trump causes
19:00 Democrats need to reinvent themselves
21:00 Trump released the Hur tapes as a distraction
23:00 Democrats should be angrier about Biden than Republicans
25:00 Mike Johnson needs Trump to pressure members of congress
26:00 Ritchie Torres joins the Chuck ToddCast
26:30 Tour of the NY-15 district
28:30 The enormity of the New York city council
30:00 Would he support expanding the size of the house?
32:00 Term limits disadvantage legislators compared to lobbyists
33:00 Can any bipartisan agreement be reached with Trump
34:30 Biden had multiple pieces of bipartisan legislation
35:30 Trump is poisoning the well in his second term
37:30 America is planting the seed of its own decline
38:00 Medicaid cuts will be devastating
40:00 Will the Medicaid cuts be delayed where a future congress could fix it?
41:30 Medicaid work requirements don't work
42:45 The consequences of the GOP budget will be barbaric
44:45 How do we address the long-term care crisis?
47:00 Should America's foreign policy be pragmatic or idealistic?
49:45 How should we view Qatar's infusion of money into American politics?
51:30 Republicans would impeach Joe Biden if he had accepted a plane
54:15 Should Democrats wield power like Trump when they're in charge?
55:50 Democrats should have spoken out sooner about Biden's decline
1:00:00 How can the Democrats project strength as a party?
1:01:15 Democrats need to let the cream rise to the top
1:02:30 Campaigning makes candidates sharper
1:03:30 Why aren't you running for NYC mayor?
1:05:30 Andrew Cuomo is a great "builder"
1:07:30 Will you run for governor in 2026?
1:08:00 How would you address the housing crisis in New York?
1:10:30 Addressing crime in New York
1:13:00 New York's budget has increased, the quality of services hasn't
1:14:45 Public ownership of utilities would lower costs for New Yorkers
1:16:30 Progressives have overprioritized ideological purity over results
1:19:15 Chuck's thoughts on interview with Ritchie Torres
1:20:00 If Torres faces Hochul 1 on 1 he could beat her
1:21:00 Rumors that Kamala Harris could run for governor of California
1:21:45 CA governor race will be tough for Harris
1:25:15 If Harris loses governor race, her political career is over
(Timestamps may vary based on advertisements)
Next Episode
Is American Pop Culture The WORST It’s Ever Been?
Chuck begins with house Republicans struggling to pass their “Big Beautiful Bill” and reflecting on the president’s ability to influence the culture versus imposing on the culture.
Then, Chuck welcomes Spencer Kornhaber, staff writer at The Atlantic to discuss his piece on contemporary pop culture and its perceived decline in quality. They dive into the impact of streaming algorithms impacting music discovery, revealing that old music now earns three times the streams of new releases as algorithms trigger nostalgia rather than innovation. The conversation explores how the music industry has lost its traditional gatekeepers, leading to a landscape where new music often sounds "rehashed and doesn't move the ball forward," while examining whether rock music has stopped evolving and how country music is experiencing a resurgence. They also tackle the growing influence of AI on music production and debate whether algorithms, despite their flaws, are actually helping people discover music in different languages and cultures.
The discussion expands to examine whether television represents the one area where pop culture is genuinely "better than ever," with prestige TV becoming the cultural center and episodic storytelling reshaping moviemaking. They explore the "Barbenheimer summer" phenomenon as evidence that theatrical experiences still matter, before diving into literature's current state amid declining readership among younger generations. They debate whether high-resolution photography and AI are diminishing visual arts, speculate about experiences becoming the next major art form for Gen Z, and examine how competition with AI might actually make human artists more innovative. They conclude by discussing the enduring popularity of live elements in sports and music—with Bad Bunny and Taylor Swift reigning as pop royalty—while questioning who truly rules Hollywood and acknowledging the surprising innovations happening in live theater.
Finally he addresses listeners’ questions in the Ask Chuck segment, weighing in on Europe’s race to rearm itself, his preferred voting method to incentivize legislative compromise and whether the questions surrounding Joe Biden’s decline will loom over the 2028 presidential race.
Timeline:
00:00 Introduction
00:30 Republicans struggling to pass the “Big Beautiful Bill”
02:00 Partisan governance is bad governance
03:30 The bill will pass, it’s just a matter of when
05:45 We’re in a “culture cold war”
08:00 Should political leaders impose culture, or influence it?
09:45 Who we elect as president is reflective of the culture
11:45 If a president imposes on culture, they impose on speech
14:45 The public will want a president who doesn’t impose on culture
17:40 Spencer Kornhaber joins the Chuck ToddCast
18:40 What inspired his piece on current pop culture being terrible?
22:25 Algorithms are terrible at introducing new music
23:10 Old music earns 3x the streams of new music
24:40 Algorithms use music to trigger nostalgia
26:10 New music sounds rehashed and doesn't move the ball forward
28:10 The music industry lost its gatekeepers
29:55 Algorithms help people discover music in a different language
32:10 Has rock music stopped evolving?
33:20 Country music is having a resurgence
34:00 The impact of AI on music production
35:40 Is television the one area of pop culture that's better than ever?
36:55 Prestige TV has become the center of the culture
38:25 How has episodic tv impacted moviemaking?
40:40 "Barbenheimer summer" wasn't a fluke
42:40 Are we also in a golden age of literature?
45:25 Younger generations are reading less
46:10 Do high resolution pictures + AI diminish the visual arts?
48:55 Will experiences become the next big artform for Gen Z
50:25 How well will his piece age?
51:55 Will competition with AI make human artists more innovative?
54:25 Will society decide to reinvest in the arts?
55:25 Gaming and sports are more popular than ever
57:10 Is the live element of sports and music driving popularity?
58:10 Bad Bunny and Taylor Swift are the king and queen of pop
59:10 Who rules Hollywood?
1:02:25 We've seen major innovation in live theater
1:04:45 Chuck's thoughts on the interview with Spencer Kornhaber
1:05:00 Algorithms suck at making culture, humans are good at it
1:05:15 Ask Chuck - Should we be concerned about Europe rearming?
1:07:55 What is your preferred voting method to incentivize compromise?
1:13:45 Will the Biden cognitive question loom over the 2028 election?
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