The Five

Episode: "The Trump Trap"
Date: August 26, 2025
Hosts: Katie Pavlich, Harold Ford Jr., Jesse Watters, Dana Perino, Tyrus, Greg Gutfeld

Overview

This episode of The Five centers around perceptions of rising crime rates in American cities, the political debate on law enforcement, and the so-called "Trump Trap"—Donald Trump’s strategy of leveraging the crime issue to put Democrats on the defensive ahead of the 2026 midterm elections. The panel debates whether Democratic mayors and leaders can or should pivot back from previous “defund the police” stances, the implications for the Democratic Party’s electoral future, and covers a mix of other trending stories, from corporate branding snafus to celebrity engagements.

Key Discussion Points & Insights

1. The “Trump Trap”: Crime as the Defining Political Issue

Timestamps: 01:04–05:44

• Greg Gutfeld launches the discussion, contrasting how President Trump and Democrats address crime, mocking the perceived “softball” treatment of President Biden by the press and suggesting Democrats are repeatedly outmaneuvered by Trump’s focus on crime.
  • Quote: "We're against crime. The Democrats like crime. I don't know why. I think crime will be the big subject of the midterms and will be the big subject of the next election... He's put them in a trap again." (01:51)
• Dana Perino notes Trump’s high-profile crackdown on crime in D.C. and how Democrats have a hard time pivoting away from progressive policies, such as defunding the police.
  • Quote: "But it seems like to me the Democrats and these mayors have gone so far off the deep end with the defund the police movement that they can't now come back to saying and admitting that actually not having police officers really has been detrimental." (03:25)
• Jesse Watters offers a political history lesson, pointing out that Bill Clinton pragmatically moved to “add more cops and get the federal government to pay for it” to win elections.
  • Quote: "What did he do? Figured out a way to do the crime bill, add more cops and get the federal government to pay for it. And he was able to win." (04:40)

2. Democrat Dilemma: Crime Policy and Political Positioning

Timestamps: 05:44–13:43

• Tyrus makes the case for dramatic action (including military deployment) to restore order, painting Democratic opposition as indefensible and suggesting “switching roles” for urban leaders as a challenge.
  • Quote: "The only reasonable way to fix this is to bring in extra help, which is in this case, our military. And we've seen amazing results. Not just that they're there, but the presence is there." (05:44)
• Harold Ford Jr.—the panel's Democratic voice—acknowledges the trap, invokes Clinton’s 1990s approach, and urges compromise: "Speaker Johnson [should] put together a massive, smart, comprehensive crime bill... you’ll get Democrats like me on television saying Democrats support it." (09:38)
• Gutfeld and Dana argue that Democrats' refusal to engage on crime, or to work with Trump on it, is alienating key voting blocs and undermining their own interests.
  • Quote (Gutfeld): "Black people want safe neighborhoods. Hispanic Americans want secure borders. It's not that difficult for the Democrats to understand." (11:07)
  • Quote (Dana): "It's really difficult to run over with a hose on the police situation when a lot of the Democrats are the ones who built this problem by saying all cops are racist and they should be defunded..." (13:31)
• Harold Ford Jr. closes the segment asserting, "Any Democrat that does a Democratic mayor doesn't want more cops. Shame on you." (13:26)

3. Political Prognosis: Is the Democratic Party Facing Extinction?

Timestamps: 15:26–23:07

• With polls and New York Times projections suggesting “the blue wall might be cooked,” the panel debates the party’s future.
• Jesse Watters and Tyrus draw analogies to dinosaurs and cicadas, poking fun at the DNC's public focus on divisive social issues instead of core concerns like crime and the economy.
  • Quote (Tyrus): "They're still campaigning against a guy that they'll never compete against again... Accept it. It's over." (17:43)
• Dana Perino criticizes Democratic Party leadership for focusing on fringe issues ("land acknowledgements," "defending terrorism," "transgender bathroom initiatives") rather than core working-class concerns.
  • Quote: "The dinosaurs didn't do this to themselves... Democrats are doing this to themselves. They can't get out of their own way at this DNC meeting." (19:20)
• Harold Ford Jr. provides perspective on party comebacks, recalling historical Democratic revivals led by Clinton and Obama. He warns that if Democrats stay mired in outdated or divisive culture wars, "we're going to be in the minority a long, long time." (22:53)

4. Cracker Barrel Controversy & Corporate Branding

Timestamps: 23:49–29:57

• The panel riff heavily and humorously on Cracker Barrel’s failed logo redesign, seeing it as symbolic of companies alienating their customer base.
• Tyrus quips, "Let’s not look at it from the political ramifications. Let’s look at it in nature... This is the last place that you can see white people in their natural habitat." (24:04)
• The discussion veers between gentle ribbing (“white restaurant?” jokes), branding missteps, and more earnest reflections on how companies should respect traditional, loyal audiences.
• Dana Perino: "If you have a good product, you just need to sell the product to a younger audience. You don't have to change the logo or try and change the culture of the place..." (28:39)

5. Fitness Challenges & The New York Times

Timestamps: 30:57–35:39

• Panelists mock a New York Times article warning about the risks of a viral “100 push-ups and 50 pull-ups in under 10 minutes” challenge. They argue media is coddling people, and that personal failing and improvement are how people grow.
• Tyrus: "If it gets people going, great. Because if you don't exercise regularly and you try this, you will fail miserably. And that's a good thing." (31:52)
• Greg Gutfeld: "They talk about the nanny state. This is the tranny state. This is so you don't have any masculinity at all in your body." (34:13)
• The segment ends with a consensus that attempting and failing physical challenges is healthy, and public discourse should encourage—not discourage—effort.

6. Pop Culture and Lighthearted Moments

Timestamps: 35:53–39:19

• The panel reacts to Taylor Swift and Travis Kelce’s engagement, trading banter about celebrity romance fatigue (Tyrus: “I got a close up. I don’t care. I don’t care. I’m not a Chiefs fan. I’m not a Swifty.” 37:12) and joking that perhaps Kelsey will now be distracted on the football field (Greg Gutfeld).
• The segment is used to highlight how public figures shape the news cycle even beyond politics.

Notable Quotes & Memorable Moments

• Greg Gutfeld (on crime as a wedge issue): "Trump's not laying a trap, he's just doing the right thing. Democrats should try that sometime." (12:50)
• Tyrus (on branding and cultural identity): "Can we not have one white restaurant? Is that okay?" (25:20)
• Harold Ford Jr. (political comeback): "You never bet against the future. And the problem Democrats have is we're clinging to the past, the old ideas, the old ways." (20:53)
• Dana Perino (on culture war): "Democrats can't get out of their own way... They still are arguing... that America is this colonialist, white supremacist nation that needs to be taken down..." (19:20)
• Jesse Watters (on DNC missteps): "This is the double down conference. They're trying to figure out... how can we most not learn our lesson from the last election." (16:24)
• Tyrus (on political challenge): "Switch with one of your constituents. In these rough neighborhoods without your team... live in that apartment for seven days with no staff, no bodyguards, nothing... See how long you last." (06:08)
• Gutfeld (on fitness challenge debate): "They talk about the nanny state. This is the tranny state... so you don't have any masculinity at all in your body." (34:13)

Segment Timestamps

• Crime & Politics: 01:04–13:43
• Democratic Party’s Future: 15:26–23:07
• Cracker Barrel Segment: 23:49–29:57
• Fitness Challenge/New York Times: 30:57–35:39
• Taylor Swift & Travis Kelce Engagement: 35:53–39:19

Tone & Style

• Spirited, irreverent, and opinionated, with a mix of political analysis, satire, and humor. Panelists often riff on each other’s comments and mix cultural references with policy commentary.
• Genuine political disagreements, but frequent lighthearted exchanges and playful jabs.

Summary Takeaway

This episode sees The Five dissect the Democratic Party’s vulnerabilities on crime and cultural issues, predicting that Trump’s focus on public safety and border security will continue to put Democrats at a disadvantage unless they adapt. The conversation highlights ongoing party rifts, the challenges of responding to public safety concerns, and touches on the risks of losing touch with traditional base voters—not only in politics, but even in the corporate world. All of this is underscored by the panel’s characteristic blend of politics, pop culture, comedic banter, and pointed commentary.