Ruthless Podcast – "How Republicans Win The Midterms – Insider Analysis"

Date: November 18, 2025
Hosts: Josh Holmes, Comfortably Smug (Michael Smith), Michael Duncan, John Ashbrook
Featured Guests: Alex Latcham (Senate Leadership Fund), Chris Winkelman (Congressional Leadership Fund)

Overview

This episode of Ruthless dives deep into the Republican strategy for the upcoming 2026 midterm elections. The hosts kick off with their signature banter and satirical commentary on current political absurdities—before featuring a rare joint interview with Alex Latcham and Chris Winkelman, the strategists running the Congressional Leadership Fund (CLF) and Senate Leadership Fund (SLF). The conversation focuses on the political landscape post-shutdown, inter-party Democratic spats, and detailed insider analysis on how Republicans plan to win and maintain their House and Senate majorities.

Main Themes

• Insider Analysis: Direct access to the "guys who are actually responsible for the nuts and bolts" of Republican strategy for House and Senate majorities.
• Election Strategy: Emphasis on message discipline, voter targeting, recruitment of quality candidates, and resource allocation.
• Democratic Civil War: Highlighting ongoing public infighting among Democrats and its potential electoral impact.
• Polling and Policy Messaging: Focusing on working families, tax cuts, and the economy as central issues.

Key Segments & Insights

1. Ruthless Banter & News Satire (00:00–12:30)

• Opening observations: The hosts riff on the seasonal shift to winter, wearing vests, and the misery of darkness:

  "All of a sudden it's like winter just hit...It's gonna be perpetual dark." (John Ashbrook, 02:26)

• Congressional scandal mockery:
  • Discussion and lampooning Dem Rep. Brad Sherman caught viewing racy images on a flight.
  • The group jokes about Sherman's blaming of the Twitter/X algorithm:

    "That's bullshit, dude…the algorithm will send you like, violence…it will not straight up. Put like naked photos on your feed." (John Ashbrook, 06:32)

  • "In saying it came on my for your tab, it's sort of telling on yourself." (Michael Smith, 07:16)

• Democratic Disunity:

  • The hosts set up the civil war brewing within the Democrat ranks post-shutdown, emphasizing attacks from the progressive side (AOC) to the establishment:

    "It was not a full throated effort by any stretch...you had AOC side attacking the Schumer side, House Democrats attacking Senate." (Josh Holmes, 10:52)

2. Interview with CLF & SLF Leadership: Alex Latcham & Chris Winkelman (20:00–53:05)

Setting the Midterm Table (20:29–22:01)

• Action-Oriented Leadership:

  "Our party has not performed well in midterms in over a decade...what's different about this midterm is that we're dealing with an executive that's extremely action focused." (Chris Winkelman, 21:01)

• Presidential vs Midterm Turnout:
  • Recognize the challenges in matching presidential turnout for Republicans in midterms.
• Senate and House strategy differences:

  "We've got 22 Republican seats that we're defending, but some really great opportunities...to expand the map and pick up a few seats." (Alex Latcham, 22:22)

Vulnerable Seats and Civil War Among Democrats (23:21–28:36)

• Most Vulnerable Dems:
  • Senate: Jon Ossoff (GA):

    "His voting record is more akin to Bernie Sanders than it is to somebody like Joe Manchin...our role is to prosecute his far left liberal voting record..." (Alex Latcham, 23:55)

  • House: 16 Democrats in Trump-won seats are priorities for Republicans.
  • Departing Dems: Jared Golden, Marcy Kaptur;

    "There is nowhere in the middle...The chair of the Blue Dog Coalition...opened up her auto repair shop for antifa rioters..." (Chris Winkelman, 25:32)

• Importance of Democrat Infighting:

  "When they pile up in the competitive seats, man, is that good news for us!" (Chris Winkelman, 28:36)

Messaging, Polling, and Closing the Deal (28:48–34:28)

• Top Messaging Issues:
  • Working families tax cut, child tax credits, "no tax on tips" messaging, affordability, inflation, and the economy.
  • Early passage and direct voter impact:

    "This bill got passed by July 4th...so people feel it when they're voting in 2026." (Chris Winkelman, 29:50)

  • Resource allocation and campaign efficiency:

    "We have better data than we've ever had about where people's eyeballs are at all times..." (Chris Winkelman, 31:59)

• Focus on Education and Voter Turnout:

  "Our voters exist and our issues are righteous...it's reminding them that, hey, there is this midterm election next year and it is critical that you show up." (Alex Latcham, 32:45)

Structural Challenges & Candidate Recruitment (34:28–44:47)

• Recruitment and Avoiding Divisive Primaries:
  • Emphasis on top-tier, general-electable candidates.

    "When I ran the NRCC last cycle, top priority was making sure that we had no unelectable candidates in general elections." (Chris Winkelman, 38:34)

  • Highlight examples: Michael Whatley (NC), Ashley Hinson (IA), Mike Rogers (MI).
• Primaries:
  • The challenge of balancing D.C. strategy with on-the-ground realities and party interests.

    "The party committee, the super pac, the White House, everybody sees the map the same way..." (Chris Winkelman, 41:32)

  • Cold hard business:

    "We're looking for candidates who will win the general election." (Alex Latcham, 43:43)

Funding, Teamwork, and the Weight of Winning (46:13–53:05)

• Unified GOP Leadership:
  • Praise for Speaker Johnson’s focus and House/Senate/White House collaboration.

    "A tremendous amount of credit to Speaker Johnson and this House Republican leadership team...these folks have found a way to stay laser focused on winning being what matters." (Chris Winkelman, 45:35)

• Strategic Spending & Early Money:

  "We have raised well over nine figures at this point. And so I don't want to get ahead of myself with the final fundraising number by end of year, but it's healthy." (Alex Latcham, 36:07)

• The Challenge of Resource Allocation:

  "The question is, are we going to have the resources needed to drive the message home?" (Chris Winkelman, 36:27)

• Macro Importance:

  "2026 is a critical election year. I couldn't be more excited." (Chris Winkelman, 50:01) "Since 1932, Republicans have only had unified control of the government four times, including now...so we do have our work cut out for us to defy history." (Alex Latcham, 50:30)

• Donor Engagement:

  "Our investors are invested in the long term in Republican policies being in place in the House..." (Chris Winkelman, 51:44) "Our challenge has been to emphasize early money...that allows us to be more efficient with your resources down the line." (Alex Latcham, 52:16)

3. Post-Interview Takeaways (53:05–55:53)

• Focus on "W's and L's":

  "The one thing that...is a takeaway...is these people are all about W's and L's, and that's it. That's it." (Josh Holmes, 53:20)

• Candidate Quality Over Ideological Purity:
  • Success is measured strictly by wins in targeted districts/states—not ideological consistency or establishment ties.

4. Listener Engagement & Variety Content (56:01–end)

• Audience Feedback: Reading listeners’ favorite "craziest Democrat moments."
• Ongoing Ruthless Segments:
  • Commentary on a dog shooting its owner, wild wolf encounters in Yellowstone, and a lighthearted roast of MSNBC’s "rebranding" and decline.
• Tonally, the episode mixes irreverence, satirical news coverage, and sharp insider political analysis.

Notable Quotes

(with Timestamps)

• "His voting record is more akin to Bernie Sanders than it is to somebody like Joe Manchin...our role is going to be to prosecute his far left liberal voting record..."
  — Alex Latcham on Jon Ossoff (23:55)
• "Our party has not performed well in midterms in over a decade...what's different about this midterm is that we're dealing with an executive that's extremely action focused."
  — Chris Winkelman (21:01)
• "If the Republican Party can just be fucking normal...I like our chances."
  — Josh Holmes on midterm outlook (17:21)
• "This is just political realignment. This is what it looks like in 20, 25 and 26."
  — Chris Winkelman on shifting voter composition (31:59)
• "You win. And that's all that matters...your job is to win."
  — Chris Winkelman (34:28)
• "Every year, Republicans have only had unified control of the government four times, including now...so we do have our work cut out for us to defy history."
  — Alex Latcham (50:30)
• "The one thing that...is a takeaway...is these people are all about W's and L's, and that's it. That's it."
  — Josh Holmes (53:20)

Key Takeaways for Listeners

• The Republican strategy for the 2026 midterms hinges on leveraging policy achievements (tax cuts, economic gains), surgical data-driven voter outreach, and ruthless efficiency with resources.
• Internal Democratic infighting is viewed as a major asset for GOP prospects, particularly as it spills over into competitive races.
• Candidate recruitment and primary management are critical focuses; avoiding divisive and costly primaries is a priority.
• Early financial contributions are essential to secure competitive advantages and maximize ad buying power.
• Winning, pragmatically defined—rather than ideological showboating or establishment favoritism—is paramount for the operatives guiding House and Senate strategy.
• The podcast maintains its signature satirical, no-prisoners tone throughout, mixing political analysis, irreverence, and sharp commentary on media absurdities.

Essential Timestamps

• 00:00–12:30: Ruthless openers, satirical banter, and mockery of political scandals
• 20:00–53:05: In-depth electoral analysis with CLF & SLF leadership interview
• 53:05–55:53: Post-interview takeaways, focus on winning strategy
• 56:01–end: Listener feedback, lighthearted segments, and closing thoughts