The Five – “When In Rome”

Date: February 20, 2026
Hosts: Dana Perino, Kayleigh McEnany, Jessica Tarlov, Jesse Watters, Greg Gutfeld

Episode Overview

This episode of The Five dives into the current political landscape with a focus on President Trump’s economic messaging during his “affordability tour” in Rome, Georgia, the Democrats’ midterm strategies (with a controversy over a “potty-mouthed” campaign ad), and a variety of hot-button issues including wealth taxes, media bias, and masculinity in American culture. The panelists engage in their signature style: spirited debate, sharp commentary, and humor, punctuated by memorable moments and pop culture asides.

Key Discussion Points & Insights

1. President Trump’s Affordability Push

(00:40 – 04:49)

• Trump’s Speech in Rome, Georgia:

  • Emphasized his administration's economic gains: “Adding $9 trillion in value to your savings... 401ks... at the highest level they've ever [been].” (01:11 – Greg Gutfeld, Jesse Watters)
  • Asserts he “won affordability”: “Because I've won. I've won affordability.” (01:24 – Greg Gutfeld)
  • Blames Democrats for previous inflation: “We inherited a mess...the worst inflation in history.” (01:41 – Greg Gutfeld)

• Panel Reaction:

  • Jessica Tarlov: Skeptical of Trump’s economic claims, highlights job losses and healthcare threats in Georgia: “Georgia lost 80,000 jobs last year since Trump took office, 27 family farms have filed for bankruptcy… premiums are going to double for 1.4 million Georgians without ACA subsidy extension, which he doesn’t back.” (03:24)
  • Kayleigh McEnany: Praises focus on economy, cites improving inflation and earnings, and suggests further populist wins are key: “If you get a few of those populist wins, I really think you could break the historical trajectory of the party holding the White House, losing in the midterms.” (05:56)

2. Democrats’ Midterm Ad & Strategy

(02:10 – 04:34, 08:51 – 11:26)

• Illinois Senate Ad:

  • Lt. Gov. Juliana Stratton’s campaign launches with a blunt message: “F--- Trump. Vote Giuliana.” (02:10 – ad segment)
  • Dana Perino: Critiques strategy: “It’s almost like a tipping point. An ad like this…does it energize them more, or does it hurt them?” (02:19)

• Greg Gutfeld: Frames this as Democrats leading with negativity vs. Republicans’ positives: “Trump leads with positives. The Democrats respond with F. Trump. ...You have a party of good thoughts versus a party of bad thoughts.” (08:51)

3. Royal Family Controversy

(11:56 – 13:56)

• Prince Andrew Arrest:
  • Stephanie Bennett reports on Andrew’s arrest for allegedly sharing confidential government documents with Jeffrey Epstein.
  • King Charles III: “Let me state clearly, the law must take its course.” (13:10 – statement summary)
  • Trump responds: “It’s so bad for the royal family, it’s very sad to me.” (13:46)

4. Media, Racism Claims, & Political Name-Calling

(14:57 – 23:05)

• Ed O’Keefe (CBS) Asks Caroline Levitt about racism accusations:

  • Watters rolls a montage of media calling Trump racist. (15:36 – 16:04)
  • Levitt & McEnany recall their own experiences fielding such questions, critiquing the repetitive use of "racist" as both hurtful and overdone.
  • Dana Perino: “It’s both the worst thing you can say... and also... kind of losing its meaning.” (18:10)
  • Greg Gutfeld: Satirizes media’s memory lapses: “It’s like when I go to you, Dana, do you remember what you did at the restaurant last night? It was very embarrassing. Right on the table.” (20:28)

• Jessica Tarlov: “We could go through the list of racist things Donald Trump has said and done...It’s old news. You want to run elections on policies people vote on.” (22:08 – 22:40)

5. Wealth Tax Debates & “Bread and Circuses”

(24:07 – 32:05)

• Bernie Sanders & Wealth Taxes:

  • Bernie Sanders: “The most significant addiction crisis in America is...the greed of the billionaire class.” (24:26 – Jesse Watters quoting Bernie)
  • Jessica Tarlov: Warns against the wealth tax, citing failed European models and the risk of driving wealthy residents out of California: “There’s going to be another round of flight if it actually goes through, I think it’s a mistake.” (26:00 – 26:49)

• Jesse Watters: Offers tongue-in-cheek “advice” to billionaires to preempt resentment: “If you’re a billionaire in California...how about you buy everybody there a $1 value meal at McDonald’s?...Do something big and bold.” (28:31)

• Greg Gutfeld: Characterizes wealth taxes as “confiscation,” not real taxation: “It’s a linguistic deception... It’s just a confiscation because no gains are being realized.” (29:54)

6. Masculinity, “Participation Trophy” Culture & Social Commentary

(32:32 – 37:27)

• Joe Rogan with Michael Jai White:

  • Discussion clip: “It’s like we’re not making men anymore. Everybody gets a trophy...These kids don’t know how to deal with loss or anything.” (33:34 – Capitas Announcer quoting podcast audio)

• Panel Reactions:

  • Greg Gutfeld: Defends participation trophies as a modern positive: “I would like people to participate.” (34:03)
  • Jesse Watters: Shares personal anecdote about refusing to display third-place trophies: “I ripped it down and I burned it in my backyard.” (35:28)
  • Jessica Tarlov: Points out the irony of Trump (the “participation trophy” critic) accepting medals and prizes, referencing the FIFA World Peace Prize: “He stole a woman [Maria Machado]’s Peace Prize himself... She had to make him his own plaque.” (36:15 – 36:52)

7. Marriage Habits and Bedtime Routines

(38:07 – 40:14)

• Bedtime Survey:
  • Couples who go to bed together are reportedly “happier.”
  • Personal anecdotes:
    • Jesse: “We just lay in bed and talk about what happened to Nancy Guthrie for hours.” (38:29)
    • Greg: Satirical take on the complexities of “women getting ready for bed.” (38:56 – 39:38)

8. Lighthearted Final Segments: Chicken Cappuccinos & Animal Noises

(40:14 – end)

• Jesse Watters tries “curuccino” (cappuccino in rotisserie chicken) from Belarus:

  • “You gotta really stick your mouth real deep in there. That’s why Em and I go to bed at the same time.” (40:52 – 41:06)

• Animal sounds game:

  • Greg: “Roll the animal sounds.” (41:19)
  • Panel attempts to guess animal calls, resulting in more banter and playful teasing.

Notable Quotes & Memorable Moments

• On Trump’s economic messaging:
  • Greg Gutfeld: “Because I’ve won. I’ve won affordability.” (01:24)
• On Democrats’ campaign ad:
  • Dana Perino: “The worst thing for me, it’s the beeps. I can’t stand it in my ear. It’s too loud.” (02:19)
• On racism accusations:
  • Kayleigh McEnany: “For 10 years, they have called Trump some rendition of racist, misogynist or xenophobe.” (17:53)
  • Dana Perino: “It’s both the worst thing you can say to somebody and ... losing its meaning.” (18:10)
• On wealth taxes:
  • Greg Gutfeld: “…not a tax. It’s just a confiscation because no gains are being realized. It’s a linguistic deception.” (29:54)
• On participation trophies:
  • Greg Gutfeld: “I would like people to participate.” (34:03)
  • Jesse Watters: “I ripped [the third place medal] down and I burned it in my backyard.” (35:28)
• On marriage routines:
  • Jesse Watters: “We just lay in bed and talk about what happened to Nancy Guthrie for hours.” (38:29)
• Rotisserie chicken cappuccino moment:
  • Jesse Watters: “You gotta really stick your mouth real deep in there.” (40:52)

Timestamps for Key Segments

• Trump’s Economic Message & Midterm Ad: 00:40 – 04:49
• Panel Discussion on Georgia, Economy & Policy: 04:49 – 08:51
• Democrat Ad and Framing of Political Narratives: 08:51 – 11:26
• British Royal Family Scandal: 11:56 – 13:56
• Racism Accusations & Media Montage: 14:57 – 19:34
• Wealth Tax, Progressive Tensions: 24:07 – 32:05
• Participation Trophy & Masculinity Segment: 32:32 – 37:27
• Happy Marriage & Bedtime Habits: 38:07 – 40:14
• Rotisserie Chicken Cappuccino & Animal Noises: 40:14 – end

Tone & Style

Throughout, the hosts blend sharp political analysis with characteristic sarcasm and banter, using humor to punctuate serious debates—showcasing classic The Five chemistry.

For Listeners Who Missed the Episode

This episode is a colorful, lively roundtable with candid takes on the election cycle, cultural flashpoints, and the everyday absurdities of politics and the media. The conversation moves from hard political analysis to lighthearted panel stories, and even a culinary adventure with rotisserie chicken cappuccino.

If you want pointed debate, genuine disagreements, and a flavor of how politics and pop culture mesh on Fox’s flagship panel show, this episode is a prime listen.