Character is destiny and no character has defined or deformed the 21st century more than Donald Trump. In this new podcast series, the definitive Trump biographer Michael Wolff joins forces with the Daily Beast’s provocateur-in-chief Joanna Coles to crack open the psyche of the man the world can’t stop watching. Coles and Wolff balance candor with curiosity as they dissect Trump’s thoughts and actions and try to answer the ultimate question: what drives the most powerful man alive? This is the analysis no one else has the access, authority, or ambition to deliver. Ignore it at your peril.
New episodes every Wednesday, Friday, and Sunday; early drops on YouTube.
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Latest episodes
Showing 20 · updated from the feed
Why Trump’s Panicked Goons are About to Lawyer Up
Michael Wolff and Joanna Coles look inside a White House bracing for the midterms, where losing the House may be expected but losing the Senate could put nearly everyone
Oct 30 1 h 02 min
Why Billions Won’t Save Trump from Crushing Defeat
Michael Wolff and Joanna Coles debate whether Democrats can take the Senate as the midterms approach, with Wolff predicting a sweeping defeat for Trump and Coles warning
Oct 28 1 h 08 min
Why Trump Will Pay the Price for MAGA’s Vilest Ad
Michael Wolff and Joanna Coles look at the Republicans’ desperate final stretch before the midterms, starting with a campaign ad so cruel that even members of their own p
Oct 25 58 min
This Is the Sordid Reason Trump Bows to Putin
In this special live show edition of Inside Trump's Head, Michael Wolff and Joanna Coles take the stage in Los Angeles to ask what Trump wants from the presidency and wha
Oct 23 1 h 33 min
I Know What Trump Will Do After Crushing Defeat
Michael Wolff and Joanna Coles look ahead to the morning after the midterms and ask what happens if Donald Trump loses control of Congress. Wolff, who watched Trump’s inn
Oct 21 47 min
I Know Who Will Go Next in Trump's Reign of Chaos
Michael Wolff and Joanna Coles go inside the chaos of Trump’s White House, where a disastrous press secretary debut, a sudden firing, and Susie Wiles’ uncertain future ex
Oct 18 1 h 07 min
This Is Trump's Sinister Plot Against His Own Aide
Michael Wolff and Joanna Coles ask whether Susie Wiles is running out of time as Trump reportedly calls around to ask what people think of his chief of staff. Wolff expla
Oct 16 58 min
I Know Real Reason Trump Fired Kimberly Guilfoyle
Michael Wolff and Joanna Coles dig into Kimberly Guilfoyle’s abrupt exit as ambassador to Greece and the leaked messages that preceded it. Why was she pushed out, and wha
Oct 14 58 min
This Is Laughable Truth About Trump's 'Tough Guy'
Michael Wolff and Joanna Coles turn their attention to Pete Hegseth, as the Secretary of Defense is facing mounting criticism over the Iran war while quietly positioning
Oct 11 44 min
Kimberly Guilfoyle's Money Secrets Just Exploded
Michael Wolff and Joanna Coles are counting down to the midterms—and the Trump world is already positioning itself for what comes next. Marco Rubio appears to be launchin
Oct 9 1 h 05 min
Why Trump's Self-Destruction Is Finally Happening
Michael Wolff and Joanna Coles examine Donald Trump’s increasingly self-destructive presidency, from his dwindling rally crowds and disastrous political bets to his reckl
Oct 7 57 min
These Are the 10 Things that Terrify Trump Most
Michael Wolff and Joanna Coles reveal the fears they believe drive Donald Trump—from being exposed as unintelligent and unable to absorb information to his dread of rejec
Oct 4 48 min
This Is Why Trump's Aides Endure his Endless Rage
Michael Wolff and Joanna Coles take a revealing look inside Donald Trump’s world of flunkies, fear and humiliation, where cabinet officials, billionaires and tech titans
Oct 2 1 h 05 min
This Is Exactly What Humiliated Trump Will Do Next
Michael Wolff and Joanna Coles dig into what Donald Trump’s political future looks like as the midterms approach, from Republicans increasingly distancing themselves from
Sep 30 1 h 01 min
This Is How Idiot Trump Is Being Played by China
Michael Wolff and Joanna Coles take a closer look at Donald Trump’s encounter with Xi Jinping and what China may have learned from a president they see as unusually susce
Sep 27 1 h 17 min
This Is Trump's Twisted New Fixation: Wolff
Michael Wolff and Joanna Coles unpack Trump’s latest threats to “annihilate” Iran, including the bizarre White House effort to find him a new word after “obliterate” appa
Sep 25 59 min
Why Floundering Trump Will Sell Out on World Stage
Michael Wolff and Joanna Coles return to dissect Donald Trump’s latest battle with the press, his launch of Trump TV, and the high-stakes arrival of Chinese President Xi
Sep 23 59 min
Why Trump’s Aides Are Finally Turning Against Him
Michael Wolff and Joanna Coles dig into what may be the most revealing signs yet of a White House struggling to manage Donald Trump, as his own advisers begin publicly pu
Sep 20 1 h 05 min
Why Trump’s Biggest Weakness Is About to Doom Him
Michael Wolff and Joanna Coles examine Donald Trump's growing political troubles as rising prices, escalating tensions in the Middle East, and his own economic policies t
Sep 18 46 min
This Is Why Cry-Baby Trump Is in Terminal Tantrum
Michael Wolff and Joanna Coles look at Donald Trump’s escalating battles with the Supreme Court, the collapse of the Kennedy Center under his control, and his increasingl
Sep 16 1 h 02 min
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Chart positions
Where Inside Trump's Head ranks today in each Apple Podcasts chart (US, Oct 30, 2026).
A curated, balanced selection of Apple Podcasts reviews.
I have learned so much from you both, and I find your banter hysterical and so spot-on. My only wish is that Michael would not talk over Joanna so much, or come across as “mansplaining.” That gets annoying as a listener because you are both brilliant. Thank you.
Joanie1970 · Sep 2026
My favorite go to podcast that attempts to make some logic and sense out of the insanity we are forced to live in. The daily or hourly news out of this administration needs some sort of explanation and some understanding- Michael and Joanna seem to tight walk the impossible trying to make sense of the insanity- Keep up the attempted explanations of the unexplainable!
SonoLuciano · May 2026
From the first few moments these two smart, analytical, calm women captured my attention. I look forward to more episodes to get their takes.
csierra7 · Nov 2024
Perfect combination of hosts with the refined and upscale Joanna Coles and the witty, biting Sam Bee providing a fun, saucy, intelligent, and intimate take on topical subjects with interesting guests. A wonderfully nourishing break from the many pure politics podcasts I consume daily.
DrDK2 · Oct 2024
I followed this podcast from the beginning and found it amusing. Though it was mostly speculation, much of the conversations rang true to me. I believed the two experienced journalists had interesting insights based on their source information. The reason I no longer follow the show is that Wolff seems a little too close to his misogynistic sources for comfort. He makes sexist comments about Coles and other women regularly, and he recently
said pro-choice means pro-abortion. He is wrong; no one is pro-abortion.
cdisillusioned · Jul 2026
We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.
Here you find the Apple Podcasts chart positions of Inside Trump's Head, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.
