The Five – "Trump & Hegseth Shred Wokeness In The Military"

FOX News Podcasts • September 30, 2025

Overview

This episode of The Five focuses on recent speeches made by former President Donald Trump and Secretary of War Pete Hegseth to military leadership at Quantico, Virginia. The panel discusses their rejection of "woke" policies in the military, the broader backlash against "wokeness" in American institutions, attacks on the legacy of the late Charlie Kirk, the consequences of progressive crime policies, and cultural conflicts underpinning current American politics.

Throughout, the Five’s signature mix of irreverent banter and pointed debate blends serious policy critique with moments of humor and cultural commentary.

1. Trump and Hegseth's Anti-Woke Military Stance

[01:03 – 05:41]

Key Points & Insights:

• Donald Trump and Secretary of War Pete Hegseth addressed top military brass, attacking "woke" standards, diversity policies (DEI), and what they characterized as distractions from military readiness.
• Hegseth advocated for a return to traditional military values, fitness standards, and eliminating "identity months, DEI offices, dudes in dresses" and "climate change worship."
  • Jesse Watters: "No more division distraction or gender delusions." [02:00]
  • Greg Gutfeld: "No more climate change worship... we are done with that." [01:58]
• Both criticized overweight and unfit military leaders:
  • Jesse Watters: "It's completely unacceptable to see fat generals and admirals... it's a bad look." [02:13]
• Trump reassured military leaders of his support, criticizing past administrations' perceived weakness.
  • Trump: "Together, we're reawakening the warrior spirit... I am with you. I support you, and as President, I have your backs 100%." [02:27]
  • He took swipes at both Biden and Obama, questioning Biden's health and leadership:
    • "They looked at him falling downstairs every day." [03:09]
    • Obama "would bop down those stairs... I said, it's great." [03:22]

Notable Quote:

"We are done with that, the era of nations or really any formation and see fat troops."
— Greg Gutfeld [02:03]

2. Media and Public Response: The ‘Woke’ Debate

[03:36 – 08:33]

Key Points:

• Mainstream and left-leaning media criticized the speeches, comparing them to heavy-handed historical militarism.
  • Juan Williams: NPR compared the gathering to Hitler assembling generals in 1935. [04:16]
• Panelists debated whether Trump’s speech was effective or performative.
  • Juan Williams: "The audience were the people that they brought in... I am all for a more aggressive posture for Department of War." [04:27]
• Critique of fitness and appearance attacks as not particularly uplifting for the military.
  • Harold Ford Jr.: "I don't understand how that was supposed to be an uplifting message..." [03:46]
• Greg Gutfeld: Framed "wokeness" as internal decay, citing appointments he characterized as unqualified and policies he described as suicidal for American strength.
  • “There was a pernicious, determined ideology that saw virtue in our weakness and viewed strength as oppressive.” [06:33]
  • He argued real threats come from within, not external enemies.
• Harold Ford Jr. added context: He preferred "Department of Deterrence" and noted technology and economic threats, particularly from China, were more pressing than ideological infighting. [08:38–10:38]

Notable Quote:

"Identity politics is the key and was the key to our own destruction. So I feel like this is progress in a big way. It's not about China or Russia or Iran. It's about us."
— Greg Gutfeld [08:23]

3. Divided on Threats: Enemies Abroad vs. Enemies Within

[10:38 – 13:47]

Key Points:

• The panel debated whether existential threats are truly internal (wokeness, division) or external (China, Russia, non-state actors).
  • Harold Ford Jr.: "I think the moment we face today, China is the thing that concerns me." [12:00]
  • Greg Gutfeld: Stressed concerns about "radicals, revolutionaries on campuses..." [12:01]
• Kayleigh McEnany: Focused on perceived military weakness under Biden, contrasting it with Trump’s assertiveness and reputation for acting decisively:
  • “They saw a commander in chief that said don't. And then they saw a Russian adversary that did in Ukraine. ... They saw weakness.” [12:16]
  • Praised Trump for military action and attempting peace deals.
• Harold Ford Jr.: Urged not to “trash everybody that came before,” recognizing shared strengths of the armed forces across administrations. [14:10]

Notable Exchange:

"I'm more scared of what I see in our cities. Radicals, the rev, the revolutionaries on campuses, the people who call us fascists, and Hitler who kill our leaders here. North Korea didn't kill Charlie Kirk."
— Greg Gutfeld [12:01]

4. Charlie Kirk’s Legacy and Attacks from the Left

[15:25 – 24:53]

Key Points:

• The panel highlighted continued liberal criticism and accusations of hate against Charlie Kirk following his assassination.
  • Kayleigh McEnany: "New York Times columnist Ezra Klein giving a platform to progressive author Tennessee Coates, failing to push back as Coats disparaged Charlie Kirk." [15:54]
  • Harold Ford Jr. (quoting Coates): "I think Charlie Kirk was a hate monger... the usage of hate... towards political ends." [15:54]
  • Ilhan Omar: "It was a legacy filled with bigotry, hatred, and white supremacy." [16:38]
• Panelists defended Kirk, with personal anecdotes of his growth, faith, and approach to civil debate.
  • Greg Gutfeld: "If Coats were to die suddenly, none of us would jump on him because you know what? We're not Coats." [18:18]
  • Kayleigh McEnany: Played a clip of Kirk calling for faith, marriage, and resisting "the sins of the flesh." [20:29]
  • Harold Ford Jr.: Emphasized Kirk's maturing viewpoints and the tragedy of his death:
    • "18, 19 year old Charlie is different than 31 year old Charlie..." [21:37]
• Criticism of left-wing commentators for failing to recognize Kirk’s commitment to free speech.
  • Jesse Watters: "He's like every one of us at this table. Save Harold." [24:12]

Notable Quote:

"I wish Charlie was alive for a lot of reasons… one of the reasons is I'd love to see him debate Mr. Coates."
— Harold Ford Jr. [22:53]

5. Crime Policy, Lax Justice, and a Father's Grief

[25:41 – 32:31]

Key Points:

• The panel reviewed a House hearing overshadowed by powerful testimony from Steve Federico, whose daughter was murdered by a career criminal due to judicial lapses.
  • Jesse Watters: Outlined how a South Carolina judge, elected in a system rife with conflicts of interest, repeatedly released offenders:
    • "This judge Price treats him like a first time offender, gives him no prison, and then this guy leaves." [27:14]
  • Harold Ford Jr.: Called for a national crime bill and argued judges should never be elected, only appointed, to minimize political or financial influence. [28:35]
  • Kayleigh McEnany: Criticized lax sentences, naming judges responsible and advocating for their removal:
    • "If you don't carry out justice and you miscarry justice... you should be off the bench." [31:14]
  • Greg Gutfeld: Framed the issue as a result of left-wing ideology romanticizing criminals and silencing dissent by labeling opponents as racist. [31:16]
  • Juan Williams: Noted the judge in question is already removed, but the systemic failures persist. [32:25]

Notable Quotes:

"The laws that allow violent thugs to live free among us were championed by left wing judges, left wing activists and sympathetic left wing press..."
— Greg Gutfeld [31:16]

6. Rosie O’Donnell’s Trump Derangement and Therapy

[33:07 – 36:29]

Key Points:

• The panel laughed at the viral clip of Rosie O’Donnell describing her struggle with Trump Derangement Syndrome and her therapist’s blunt response.
  • Rosie O’Donnell: "My therapist said, why are you so upset? And I said to her, why are you not." [33:32]
  • Greg Gutfeld: "What would you rather be Rosie's therapist or Don Lemon's proctologist?" [33:43]
• Jesse Watters argued that for certain celebrities, constant political outrage is necessary to maintain relevance.
• Kayleigh McEnany: Mocked O'Donnell’s move to Ireland, questioning the authenticity of “protect your sanity” when she voluntarily joins U.S. media events again.

7. Workplace Humor & Culture

[37:03 – 39:57]

Key Points:

• Debate over research suggesting humor in the workplace is risky.
  • Greg Gutfeld: Joked about their own irreverence; "That's why we put in that stripper pole." [37:49]
  • Harold Ford Jr.: Bemoaned declining tolerance for off-color jokes.
  • Kayleigh McEnany & Jesse Watters: Joked about their own office antics, arguing some lightheartedness is necessary for morale.

8. One More Thing: Lighthearted Roundup

[40:29 – 42:29]

Key Points:

• Greg's "Invincible Squirrel News": a humorous story about a brave squirrel.
• Banter about linguistic origins of the word "axe" and "y'all."
• Stories of kindness (a surprise wedding in a hospital).
• Highlights for upcoming Fox News and Jesse Watters' shows.

Memorable Quotes

• "No more division distraction or gender delusions." — Jesse Watters [02:00]
• "Identity politics is the key and was the key to our own destruction. So I feel like this is progress in a big way. It's not about China or Russia or Iran. It's about us." — Greg Gutfeld [08:23]
• "If you don't carry out justice and you miscarry justice... you should be off the bench." — Kayleigh McEnany [31:14]
• "You can disagree with someone, but this... Is this going overboard? Has it gone overboard?" — Harold Ford Jr., on media fixation with Trump [34:54]
• "18, 19 year old Charlie is different than 31 year old Charlie." — Harold Ford Jr. [21:37]
• "If we do get reparations, I'll make sure you get your point 1%." — Harold Ford Jr. to Jesse Watters [24:47]

Timestamps of Import

• [01:03] Episode proper begins with Hegseth and Trump at Quantico
• [02:27] Trump’s remarks to the military
• [03:36] Media reaction and panel responses
• [06:33] Greg Gutfeld’s “enemy within” monologue
• [12:16] Kayleigh McEnany on Biden’s foreign policy “weakness”
• [15:25] Segment about Charlie Kirk’s legacy and left-wing criticism
• [20:29] Audio of Charlie Kirk discussing faith and values
• [25:41] Story of Steve Federico, grieving father
• [31:16] Gutfeld on political culture and crime
• [33:07] Rosie O’Donnell’s Trump Derangement segment
• [37:03] Panel’s take on workplace humor
• [40:29] “One More Thing” – lighthearted closing round

Tone:
Conversational, irreverent, and often tongue-in-cheek, but with sharp, often serious undertones when addressing key social and political themes. The panel displays palpable ideological alignment but is not monolithic, offering some internal debate (especially from Harold Ford Jr. and Juan Williams).

Summary:
For listeners, this episode covers the culture wars permeating the military, criminal justice failures, the media's handling of conservative figures, and the personal impact of political division. It’s a blend of policy critique, cultural commentary, and humor—packaged in The Five’s characteristic, lively discussion.