Podcast Summary
Podcast: Keeping It Real: Conversations with Jillian Michaels
Episode: Donald Trump Jr Drops Bombshells: Thomas Crooks, Gaza, Russia, Iran, Mamdani, 2026 Midterms
Date: November 30, 2025
Host: Jillian Michaels
Guest: Donald Trump Jr.
Overview
This episode of “Keeping It Real” features a deeply candid and wide-ranging conversation between Jillian Michaels and Donald Trump Jr. They tackle controversial topics head-on, including the assassination attempt on Donald Trump Sr. (Thomas Crooks), skepticism about the official narrative, U.S. foreign policy (Russia/Ukraine, Gaza, Iran), economic challenges, the changing landscape of both political parties, culture wars, and the upcoming 2026 midterms. The tone is frank, adversarial yet respectful, and often peppered with personal anecdotes and notable quotes.
Key Discussion Points
The Trump Family Experience with Public Perception and Threats
- Pressure and Polarization: Jillian opens with how deeply polarizing the Trump family is, comparing reactions to being called “the second coming of Hitler and Jesus.”
- Don Jr. on Family Strain (04:22):
- “It’s hard. ...I had Democrats literally try to throw me in jail. They called my father every name in the book.”
- He describes his instinct to keep fighting, the emotional toll on his children, and mixed reactions they receive from the public.
- Anecdote from Trump Sr. (06:09):
- “And now we find out who our real friends are.”
- Don Jr. recounts his father’s early understanding of the costs of running for president.
The Thomas Crooks/Assassination Attempt Controversy
- Suspicion and Rabbit Holes (08:35, 09:27):
- Jillian expresses skepticism about the official story: the shooter’s ease of access, encrypted phones, possible coordinated effort.
- Don Jr. acknowledges the oddities:
- “A guy with a rifle was allowed to get within 130 yards of the presumptive nominee… the whole thing definitely feels odd to me.”
- He trusts Secret Service’s Sean Curran but maintains skepticism about broader federal agencies:
- “They would never let that happen to Obama… but... raid Mar-a-Lago? That’s an intimidation tactic.”
- Conspiracies vs. Truth: They both struggle with distinguishing “insane” theories from genuine causes for concern.
- (12:04) Don Jr.: “I also want to make sure we actually get the truth. That’s what I actually want.”
The Threat of Partisan Weaponization and the 2026 Election
- Fear of Escalation (12:59):
- Jillian: Concern for further indictments or retaliation if Democrats win.
- Don Jr.: “The Democrats have shown—there’s nothing they won’t do... rules for me, but not for thee with them.”
- Resilience and Adaptation:
- “We have to be playing the same game as the other side. ...My dad doesn’t really lose sleep over these things.”
Foreign Policy: Russia/Ukraine, Gaza, Iran, and Economic Ramifications
- Trump’s Claims and Accomplishments (14:24–17:08):
- Jillian lists Trump Sr.’s claims: de-escalating multiple conflicts, global markets strength, lower gas prices, “tenuous” Gaza ceasefire, and negotiations with Russia/Ukraine.
- Don Jr.: “There’s no money in peace, Gillian.”
- On Ukraine: “If America stopped funding any of this stuff, this thing would be over in two weeks.”
- On foreign aid and U.S. priorities:
- “Fentanyl kills 100,000 Americans a year. Like, that’s two Vietnams a year.”
- Corruption and Realism:
- Don Jr. tells an anecdote from Monaco on Ukrainian luxury cars as evidence of corruption (17:42):
- “They’re stealing that money, and it’s just one big corrupt scandal.”
- Don Jr. tells an anecdote from Monaco on Ukrainian luxury cars as evidence of corruption (17:42):
- Messaging and Partisan Spin:
- Trump supporters get criticized regardless of outcome.
- “If Donald Trump cured cancer tomorrow, they’d be like, but he didn’t cure this.”
- Trump supporters get criticized regardless of outcome.
Israel, Gaza, Nuance and Non-Binary Politics
- Nuanced Positions vs. Binary Fights (26:54):
- Don Jr. laments the lack of middle ground, especially post-Charlie Kirk’s murder.
- “There is a middle ground. ...You can be effective because you’re not just a career bureaucrat.”
Iran and the Middle East (After 60:32)
- Questioning Policy Consensus:
- Don Jr.: “He [Trump] did almost have them [Iran] bankrupt with the sanctions. And then Joe Biden came in and they sent him pallets of cash…”
- On his father’s method: “If we create stronger alliances with their actual neighbors… his response was actually the perfect one...It was over in 20 minutes.”
The Economy, Immigration, and National Priorities
- Incremental Progress vs. Instant Gratification (28:54, 33:21):
- Don Jr.: “None of that happens overnight. ...We live in an instant gratification world.”
- On immigration: negative net migration is a result of changing incentives, not mass deportation.
- Jobs, Investment, Tariffs (34:50–35:00):
- Tariffs leading to hundreds of billions in new revenue; reshoring jobs as long-term strategy.
- Tough Love and Disciplinarian Leadership
- Don Jr.: “My dad is the disciplinarian parent we all need.”
- Advocacy for generational, not short-term, thinking in economic and geopolitical strategy.
Culture Wars, the GOP and the Expanding Tent
Gay Rights and Trans Issues
- Shifts in Conservative Views (42:23–44:59):
- Jillian: “I personally want to say thank you. I had a complete misconception about who your dad was going to be… I was wrong.”
- Don Jr.: “Honestly, if you’re an adult...do your thing, I don’t really care. ...But stop indoctrinating and manipulating children.”
- On recidivism and youth transition: “For any of these minors who undergo these procedures it’s like 93%.”
- Opening the Tent:
- Jillian: “Your father and your family has built a far bigger and more accepting tent than the left.”
The Far Right, Disavowing Extremism, and the “Fracture”
- Fuentes, Carlson, and the New Right (48:52–51:48):
- Jillian: Urges the right to more forcefully disavow vile and racist voices.
- Don Jr. is torn:
- “I think some of those radicals…they almost cancel themselves.”
- Prefers open conversation to cancel culture: “If you hear some people speak and you don’t like it, they almost cancel themselves.”
- Warns about “manufactured crises” pushed by neocons and foreign actors.
- “I’m sort of a free speech absolutist, but that doesn’t mean there’s not consequences to that speech.”
Looking to the Future
Will Don Jr. Run? (52:27)
- “Oh God…You never know…My primary focus is just trying to make sure my father’s agenda gets done and accomplished.”
Trump’s Long-term Vision (55:13)
- Prosperity for Americans, ending endless wars, reestablishing the American dream, and tough, realistic economic strategy.
- “He would much rather save a few hundred thousand lives than get an award. ...He wants to bring back the prosperity that America really had such a great benefit of, that our politicians have destroyed.”
Advice from Don Jr. to Americans (64:56)
- “Turn off your televisions, stop listening to the mainstream media, have a conversation [with someone who disagrees with you].”
- Advocacy for critical thinking and long-term perspective:
- “Ask yourself…is this going to be good for your country in the long term?”
Notable Quotes (with Timestamps)
-
On Family and Public Scrutiny:
- “They called my father every name in the book. ...They created so much rhetoric that multiple people tried to kill him.” – Donald Trump Jr. (04:55)
-
On the Trump Assassination Attempt:
- “A guy with a rifle was allowed to get within 130 yards of the presumptive nominee… the whole thing definitely feels odd to me.” – Donald Trump Jr. (08:52)
- “You never give up the high ground.” – Donald Trump Jr. (09:27)
-
On U.S. Foreign Aid and Priorities:
- “Fentanyl kills 100,000 Americans a year. Like, that’s two Vietnams a year. And we’re supposed to let that go so we could focus on Ukraine?” – Donald Trump Jr. (23:27)
-
On Economic Mess:
- “We have to play in the real world, not in some sort of... fake reality. This isn’t Oz.” – Donald Trump Jr. (30:01)
- “Politicians ...make terrible decisions to win an election in two weeks. But now you’re saddled with that… for literally generations.” – Donald Trump Jr. (33:46)
-
On Trans Rights and Sports:
- “You can be pro Israel, but not entirely for the actions of the government that rules it right now.” – Donald Trump Jr. (26:54)
- “If you said anything about it, you’re also a Nazi.” – Donald Trump Jr. (40:45)
- “If you’re an adult...do your thing, I don’t really care...But stop indoctrinating and manipulating children.” – Donald Trump Jr. (42:48)
-
On Internal GOP Debate and Extremists:
- “They almost cancel themselves... Sometimes you just have to let the idiocy just go out there.” – Donald Trump Jr. (51:10)
-
On the American Dream and Trump’s Vision:
- “He wants to bring the prosperity that America really had such a great benefit of, that our politicians have destroyed over years…” – Donald Trump Jr. (55:38)
- “A weak America with feckless leadership is not just bad for America, it’s actually bad for the entire world.” – Donald Trump Jr. (55:38)
-
On Advice to Listeners:
- “Turn off your televisions, stop listening to the mainstream media, have a conversation with someone who disagrees with you.” – Donald Trump Jr. (64:56)
Memorable Moments and Dynamics
- Personal anecdotes: Don Jr. shares stories about family life under siege, interactions with his father, and business trips that frame his worldview.
- Blunt Honesty: Both host and guest lay out controversial opinions on the politicization of law enforcement, war, gender issues, and media manipulation.
- Across-the-aisle respect: Despite policy disagreements, Jillian openly thanks the Trumps for defying her preconceptions and making the right “more open.”
- Nuanced criticisms: Jillian pushes back on messaging failures, risks of extremist influence, and the allure of “instant gratification” among voters.
- Calls for true dialogue: The episode closes with an appeal for open, respectful conversation across political divides as essential for the country’s future.
Important Timestamps (MM:SS)
- 03:23 – Jillian asks how it feels for the Trump family to be so polarizing.
- 06:09 – Don Jr. recounts Trump Sr.’s “now we find who our real friends are” quote.
- 08:27 – Jillian introduces skepticism about the Thomas Crooks shooting narrative.
- 15:22 – Evaluation of Trump Sr.’s claims about economic and foreign policy success.
- 17:42 – Story about Ukrainian luxury cars in Monaco and alleged corruption.
- 23:27 – Don Jr. prioritizes fentanyl fight over Ukraine war aid.
- 28:54 – Discussion about instant gratification and economic change.
- 33:46 – The generational consequences of short-term political decisions.
- 42:23 – Jillian thanks the Trumps for being more open on gay rights.
- 48:52 – Debate about handling Nick Fuentes and right-wing extremism.
- 55:13 – Don Jr. describes Trump’s legacy and vision.
- 64:56 – Final advice: “Turn off your televisions… have a conversation with someone who disagrees with you.”
Takeaways
This frank, lengthy dialogue navigates the sharp edges of America’s culture and political wars while offering thoughtful (if combative) perspectives on current events. Don Jr. positions the Trump family as uniquely willing to take hard stands, transform the GOP, pursue peace and economic strength, and call for more critical, nuanced thinking—while resisting both left- and right-wing extremism. The episode serves both as a combative critique and as a plea for honest, face-to-face conversation beyond the headlines and tribalism.