Ruthless Podcast – Episode Summary

Episode Title: Mugged By Reality: Mamdani Is Already In Trouble + Todd Ricketts Joins The Progrum
Date: February 20, 2026
Hosts: Josh Holmes, Comfortably Smug, Michael Duncan, John Ashbrook
Special Guest: Todd Ricketts (Owner, Chicago Cubs)

Episode Overview

This “Fun Time Friday” episode of Ruthless is a classic blend of sharp conservative analysis and irreverent humor as the hosts break down the latest headlines, skewer progressive politics, and chat with Chicago Cubs owner Todd Ricketts. The show kicks off with a deeper look at New York City’s budget woes and progressive governance (“Mamdani is already in trouble”), pivots to the spectacle of Democratic politics, does a comedic review of Eric Swalwell’s “erotic poetry,” and closes with an insightful yet light-hearted interview about sports, media, and culture with Ricketts.

Key Discussion Points & Insights

1. Mugged by Reality: Mamdani, New York, and the Progressive Trap

[00:00 – 18:25]

• Host analysis:
  The discussion opens with sharp criticism of New York City’s new progressive leadership—specifically referencing councilman Zohran Mamdani—and a satirical breakdown of the consequences of aggressive social spending and “budget extortion.”

  Key points:

  • Mamdani’s proposed city budget ($127 billion for 8.4 million, bigger than Florida’s $117 billion for 23.4 million) is mocked as unsustainable and a prime example of progressive fiscal irresponsibility.
  • “This is like some jokerfied thing. He’s like, I’m going to burn this pile of money while all of you watch.” – Smug [00:26]
  • The “moderate Democrat” myth is dismantled using Virginia’s Abigail Spanberger as an example; even so-called moderates are chasing business out and trying to ensure one-party rule via redistricting.
  • Hosts argue that for Democrats, it’s all about “power,” not policy—encapsulating a broader skepticism of government growth and left-wing motivations.
  • “What these libs want is power. The only thing Spamberger wants is power, Mom. Donnie, all he wants is power. They trick people into choosing them so they can get the power.” – Holmes [05:34]

  Notable moment:

  • Comparisons between the U.S. teachers unions and Japanese education funding highlight the alleged waste and corruption in Democrat-controlled cities.

2. The Incremental Playbook and the Expanding Overton Window

[18:25 – 20:43]

• Trendspotting:
  Hosts argue that New York’s troubles are a preview for what progressives will bring everywhere, referencing Minnesota, Virginia, and the purported dynamic where Democratic “moderates” simply follow the activists’ lead.

  • “If you thought the left had really shifted the Overton window and gone out to the extremes, they haven’t gotten started yet.” – Smug [16:29]
  • The rhetoric about “taxing the rich” is challenged as targeting W2 earners and entrepreneurs, not true billionaires.
  • “What they always settle on in ‘tax the millionaires’ is like the W2 worker.” – Duncan [18:37]

  Populist critique:

  • The hypocrisy of progressive elites is again a major theme, especially their immunity from the policies they promote (defund the police, higher taxes).

3. Comedic Relief: Swalwell’s Erotic Poetry

[23:04 – 30:19]

• Segment highlight:
  The hosts do a dramatic reading and over-the-top roast of Eric Swalwell’s college-era “erotic poem.”
  • “[Atop my hotel she stopped, I left for cloth and tan, My anxious arm she bit. My scar is beautiful.] What? What? … Is this a crime scene?” – Ashbrook / Smug [26:06]
  • The bit is a blend of cringe comedy and political mockery with the consensus being that its pretentiousness is indicative of a larger “pain or deficiency” in progressive leaders.

4. Trump’s Political Standup

[31:52 – 41:40]

• Standup Politician:
  A montage of Trump’s recent and vintage remarks demonstrates what the hosts see as his unique, authentic, irreverent style that connects with audiences beyond policy.
  • “One of the highest compliments Trump can pay somebody is that you did such a good job, people are saying, why can’t Trump do it? Yeah, don’t show me. That is an incredible compliment.” – Smug [35:02]
  • “Women, I like. Men? I have any interest. Good. That’s right. That’s right.” – Donald Trump riffing to an audience [36:18]
  • The hosts contrast Trump’s “one-of-one” comedic political delivery with other politicians’ sterile or inauthentic messaging, noting this is why “people are gonna vote for that – it’s funny, it’s real.” – Holmes [35:53]

5. Parenting Group Chat Drama: When Activism Infects Everyday Life

[47:52 – 61:56]

• Cultural analysis:
  The panel reviews a Washington Post story about a D.C. “parenting WhatsApp group” that devolved into bitter political schisms over Gaza and ICE.
  • “You signed up, you’re in a mom’s group chat. You want to know when to sign up for the baseball team. Next thing you know, you’re talking about fucking Gaza.” – Duncan [53:00]
  • They explore how “activist fervor” takes over community groups, making cultural and ideological signaling more important than the supposed purpose (parenting/kids).
  • “It is a disease, but that’s what we’re finding out.” – Duncan [61:57]
  • Satirical jabs highlight the disconnect between performative activism and real community concerns.

6. Interview: Todd Ricketts on Baseball, Business, and Media (Owner, Chicago Cubs)

[63:25 – 90:58]

Baseball & Ownership

• MLB’s future: Ricketts discusses the need for a salary cap/floor to increase league competitiveness, referencing the upcoming CBA talks (67:28).
• “We need to make some structural changes in baseball to kind of level that playing field and make the teams competitive.” – Ricketts [66:35]
• Wry discussion of NL Central’s tradition and rivalry, and background stories about the Cubs and Wrigley Field.

Real Estate, Stadium Economics & Fan Culture

• Stadiums and development: Modern ownership means investing in not just the stadium but transforming the surrounding area for fan experience and economic viability.
• “If I’m going to put my own capital in the stadium, I’m going to have some ownership.” – Ricketts [71:34]
• Anecdotes about Wrigleyville landmarks and development projects.

New Media Ventures: FreeSpoke Search Engine

• Balanced information: Ricketts introduces FreeSpoke, an AI-powered search engine designed in response to perceived liberal bias in Google/search and social.
• “We try to meta tag everything the best we can and surface things kind of equally and in a balanced way.” – Ricketts [77:20]
• Technical talk about how FreeSpoke built its own Internet index, not just scraping Google/Bing.

Personal Q&A (rapid fire)

• Last meal? Pizza (“I like pizza more than I like being skinny.”) [84:35]
• Hidden talent? Would love to be a singer, but is “the worst singer on the planet.” [86:06]
• Motivation? Hates losing. “You gotta taste it in your throat when you lose.” [88:37]

Notable Quotes & Memorable Moments

• On progressive budgeting:
  “It’s like some jokerfied thing. He’s like, I’m going to burn this pile of money while all of you watch.” – Smug [00:26]

• On the myth of the moderate Democrat:
  “There is no such thing as a moderate Democrat to begin with.” – Smug [04:18]

• On taxes and socialists:
  “The only difference … is that Mamdani is actually telling you in the campaign, ‘No, I really want Red China here.’” – Duncan [05:06]

• Union critique:
  “Don’t confuse teachers unions for teachers.” – Holmes [09:11]

• Swalwell poetry roast:
  “She exploded. Blood rolling down our chin.” – Ashbrook [25:52]
  “Is this a crime scene?” – Smug [25:55]

• On Trump’s authenticity:
  “You want to be entertained…It’s the same reason you buy a Shane Gillis ticket or a Dave Chappelle ticket. You want to look like life is difficult enough.” – Duncan [40:08]

Timestamps for Key Segments

• 00:00 – 10:01: Mamdani, NYC budget, teachers unions
• 10:01 – 18:25: Eric Adams’s “leverage,” extorting taxpayers
• 18:25 – 20:43: The myth of moderate Democrats, tax the rich
• 23:04 – 30:19: Swalwell's poetry gets roasted
• 31:52 – 41:40: Trump humor, political authenticity
• 47:52 – 61:56: DC parenting group chat civil war
• 63:25 – 90:58: Interview: Todd Ricketts (Cubs, stadiums, FreeSpoke)
• 84:06 – 89:56: Todd Ricketts personal Q&A

Tone & Language

True to the Ruthless brand, this episode blends sarcastic wit, outright mockery, inside-baseball political takes, and some brash but playful bravado. There’s a genuine affection for irreverence, a willingness to critique both foes and friends, and a sense of camaraderie built on shared cultural and political grievances.

Takeaway

A high-energy episode that perfectly mixes conservative skepticism, biting humor, and political analysis–with a side of baseball and a dash of new-media entrepreneurship. If you want to understand the intersection of conservative culture, political activism, and how the Right thinks about self-mockery versus the Left’s self-seriousness, this is the show for you.