The Five – "Portnoy Ditches The Dems"
FOX News Podcasts | November 17, 2025
Panelists: Jesse Watters (Host), Kayleigh McEnany, Harold Ford Jr., Dana Perino, Greg Gutfeld
Overview
This episode of The Five zeros in on the Democratic Party's struggles to connect with young men—sparked by media mogul Dave Portnoy's disillusionment with Democrats. The panel debates cultural shifts, masculinity in politics, demographic trends among voters, and recent news on the Epstein files. They also cover protest antics outside ICE facilities and discuss Michelle Obama's remarks about sexism and the American presidency.
Key Discussion Topics and Insights
1. Dave Portnoy & The Democrats' "Man Problem"
Segment starts at [01:04]
Main Points:
- Dave Portnoy's Critique: The Barstool Sports founder bailed on Democrats, saying the party alienates "normal guys" and traditional masculinity.
- Male Alienation: Panel explores how young men feel labeled as “toxic” simply for enjoying traditional activities or wanting to succeed, leading to a loss of Democratic support.
- Cultural Shifts: Greg Gutfeld and Dana Perino argue the culture now demonizes traits and interests historically valued among men—like competitiveness, family-raising, and ambition.
- Political Communication & Policy: Harold Ford Jr. and Kayleigh McEnany stress Democrats need effective policies and better communication, not just new spokespersons.
- Rise of Podcasts: Kayleigh points to Trump's success with young men partially due to appearing on populist podcasts, attracting audiences disenchanted with mainstream liberal figureheads.
Notable Quotes:
- Greg Gutfeld [03:43]:
"We don’t mind being the butt of jokes... but when you start calling us evil, we’ll show our way out."
- Dana Perino [06:05]:
"White men became the scapegoat for everybody's grievances and where that only leads to problems. Not only did the Democrats lose white men, but so did corporate America."
- Kayleigh McEnany [09:36]:
"They’re out there trying to say, ‘let’s have a liberal Rogan...’ The key is not finding a liberal Joe Rogan. The key is changing policies."
Memorable Moments:
- Lighthearted ribbing over alcohol as social lubricant ([09:20]), and a deeper debate about teaching young men confidence without substances ([12:09]).
2. Epstein Files, Dems on Defense
Segment starts at [14:21]
Main Points:
- Trump Calls for Epstein Files' Release: Trump reverses his prior stance, urging full transparency while emphasizing Democrats' alleged connections.
- Leaked Communications: Accusations surface that Rep. Stacy Plaskett was communicating with Jeffrey Epstein about political strategies during a 2019 hearing, drawing media scrutiny.
- Panel Skepticism: Jesse Watters and Kayleigh McEnany downplay any alleged Trump link, but predict damaging revelations for some Democrats and institutions, pointing to past donations and associations.
- Media Spin: Greg Gutfeld claims the media will exploit any ambiguity in the files to attempt guilt by association for Trump or Republicans.
Notable Quotes:
- Jesse Watters [16:13]:
"You can’t release everything. A lot of it’s... classified national security. But whatever’s out so far is already no smoking gun."
- Greg Gutfeld [20:47]:
"A Democrat congresswoman was being prepped in real time by a convicted sexual predator in a hearing... If this were Republican, it would be worse than Watergate, 9/11, and Iran-Contra tied together."
3. ICE Protests—‘Sweating Out the Fascists’
Segment starts at [25:39]
Main Points:
- Aerobics as Protest: Demonstrators outside a Portland, OR ICE facility don 80s leotards and perform group aerobics—targeted at stopping ICE detentions.
- Seriousness vs. Silliness: Panel mocks the effectiveness, with Gutfeld noting he prefers silly protest theater to violence, but critiques its detachment from real immigration issues.
- Enforcement Policy: Jesse Watters discusses deportations, migration rates, and the need for tough action; Harold Ford Jr. acknowledges the right to peaceful protest but prioritizes the removal of violent criminal aliens.
- Disconnect: Dana Perino laments that outlandish protests do more to spotlight activists than help immigrants truly in need.
Notable Quotes:
- Greg Gutfeld [27:29]:
"This is more about the protester than the protest. These are not serious people... they don’t have practical answers to social and economic consequences."
4. Michelle Obama & The "Sexism" Claim
Segment starts at [32:25]
Main Points:
- Obama’s Claim: Michelle Obama says America isn’t mature enough for a woman president; panel reacts with incredulity, saying previous female candidates fell short on merit, not due to sexism.
- Challenging the Narrative: Panelists argue the country is ready for a woman leader if the candidate inspires confidence—highlights leadership examples from other nations.
- Perception & Politics: Jesse Watters and others criticize Obama as a "whiner," suggesting her stance is out-of-touch and lacks substantive policy positions.
Notable Quotes:
- Dana Perino [33:38]:
"Give us someone to root for. Give us somebody who isn’t on the wrong side of every issue."
- Kayleigh McEnany [37:57]:
"Give America a Margaret Thatcher and I think you will see a woman get elected. The problem has been the quality of the candidates, not the gender of the candidate."
5. "Fastest"—Bill Ackman's Dating Advice
Segment starts at [39:18]
Main Points:
- Ackman's Advice: Billionaire Bill Ackman suggests men should simply ask, "May I meet you?" in person to move beyond online conversations.
- Panel Reactions: The group mocks the formality of the line, joking its awkwardness could scare women off. Gutfeld points out Ackman’s privilege by virtue of his status and looks.
- Connection to Earlier Topics: Dana ties this back to the broader issue of young male social skills in the digital age.
- Consensus: Despite some laughs, the core advice—have real, face-to-face conversations and accept rejection—is seen as sound.
Notable Quotes:
- Greg Gutfeld [40:34]:
"A serial killer acts subservient, right? ... If a guy is like, 'may I meet you?' That means he’s got a crawl space with your name on it."
Timestamps for Key Segments
- Portnoy & Young Men: [01:04] – [13:10]
- Epstein Files Discussion: [14:21] – [23:14]
- ICE Protesters: [25:39] – [31:34]
- Michelle Obama & Sexism: [32:25] – [38:21]
- Bill Ackman Dating Advice: [39:18] – [41:41]
Memorable Moments & Panel Banter
- Greg Gutfeld's Satirical Jabs:
"If the Rockettes called me and said, come over, we’re hot tubbing, I’d say, I don’t know, can you come over? I have a tub." ([03:13])
- Jesse on Gender Politics:
"I'm still not ready to vote for a woman." ([38:21])
(Delivering the line deadpan, drawing laughter for undercutting the seriousness of the previous discussion.)
Conclusion
This episode underscores a recurring theme on The Five—culture war anxieties and shifting political allegiances, especially among young men, in the wake of changing norms and identity politics. The panel offers a mixture of heated analysis, satire, and personal anecdotes, ultimately urging political parties to focus on substantive, broadly appealing policies rather than media strategies or identity-based messaging.