Orange Is the New Orange: Trump Just Might Go to Jail

Michael Wolff joins Joanna Coles as the Epstein email deluge crashes straight into Donald Trump’s White House, leaving the president uncharacteristically mute and visibly cornered. Wolff argues this is the moment he’s warned about for years—the Trump–Epstein relationship finally breaking into full view. As newly released emails hint at suppressed testimony, secret negotiations, and a “dog that hasn’t barked,” Joanna presses Wolff on why MAGA is demanding total transparency even as it risks politically detonating Trump himself. Wolff explains why Ghislaine Maxwell’s family may now be threatening leaks to pressure the White House, and why Trump’s go-to strategy—delay—may not work against a story that resurfaces again and again. What does Trump do when the one scandal he can’t outtalk finally catches up with him? Hosted on Acast. See acast.com/privacy for more information.

16 Marras 202535min

Jonathan Karl joins Joanna Coles to reveal the chaos inside Donald Trump’s orbit. Karl, ABC News’ chief Washington correspondent and author of the new book Retribution, calls Trump’s relationships “abusive,” with aides, journalists, and anyone nearby alternately lavished with attention and publicly humiliated, praised, and discarded. They also dig into reports of Trump’s poor diet, bad sleep hygiene, and total aversion to exercise, which open up a larger conversation about a leader showing unmistakable signs of physical wear. Hosted on Acast. See acast.com/privacy for more information.

14 Marras 202541min

Michael Wolff joins Joanna Coles to shed light on his email correspondence with Jeffrey Epstein and its impact on President Donald Trump. Drawing on leaked emails, private conversations, and years of reporting, Wolff exposes how the resurfacing of the Epstein files is reopening dangerous cracks inside Trump’s circle. Coles pushes him on what’s fact, what’s myth, and what Epstein really knew. As Trump fights to control his comeback narrative, Wolff posits one haunting truth: Epstein’s shadow may be the one story he can’t spin away. Hosted on Acast. See acast.com/privacy for more information.

13 Marras 202534min

Michael Wolff joins Joanna Coles to unpack Trump’s tangled web of the Epstein files and Ghislaine Maxwell’s looming possible pardon. From the back in action Congress maneuvering to demand documents across the FBI, Justice Department, and multiple federal districts, to the astonishing perks Maxwell enjoys behind bars, Wolff and Coles trace the threads that link influential players, past crimes, and potential cover-ups. They dive into the “out-in-the-open” maneuvers protecting key witnesses, and what it all means for Donald Trump’s ongoing exposure. Hosted on Acast. See acast.com/privacy for more information.

12 Marras 202543min

Symone Sanders Townsend joins Joanna Coles to break down the moment Donald Trump struggled to stay awake for twenty minutes in the Oval Office, and why the fact that no one around him reacted is the real story. Sanders, co-host of “The Weeknight,” on MSNBC soon to be MS NOW starting on November 15th, outlines the mystery of who’s really running the White House to the gold “Oval Office” signage, the secretive East Wing demolition, and the advisers suddenly speaking in “I” and “we,” Symone exposes a presidency drifting without leadership. In the end, Symone leaves us with the fundamental question: If Trump can fall asleep on camera and his deputies shrug, who’s actually in charge? Hosted on Acast. See acast.com/privacy for more information.

11 Marras 202544min

The Daily Beast’s must-read columnist David Rothkopf joins Joanna Coles to dissect Trump’s mounting political peril. As dissent grows within his own party—over foreign aid, tariffs, and radical Senate moves—Rothkopf warns that Trump is “staring death,” with his political survival hanging by a thread. This episode explores the stakes of a president confronting resistance from his base and the chilling question: how far will he go to stay relevant? Hosted on Acast. See acast.com/privacy for more information.

10 Marras 202539min

Michael Wolff joins Joanna Coles to examine the looming legal battlefield of Trump’s 2026 strategy, where every move is filtered through lawyers and litigation. As the White House braces for the possibility of losing both the House and Senate, Wolff reveals the unraveling logic guiding a president who cannot course-correct, while aides scramble to protect their careers. From redistricting schemes to potential Supreme Court battles over voting rights, this episode shows how Trumpworld is preparing for an election fought not just at the polls—but in the courts. Joanna asks the central question: Can anything stop this legal juggernaut? Hosted on Acast. See acast.com/privacy for more information.

9 Marras 202538min

Michael Wolff joins Joanna Coles to examine the one thing Trump can’t spin: a morning of losses he instantly tries to recast as wins. Wolff brings the voices inside the West Wing, describing Trump pacing between TVs, hunting for a villain, mangling the numbers, and turning Mamdani into his next made-to-order enemy. They cut through the chaos—shutdown brinkmanship, Prop 50 conspiracies, the Cuomo curveball, and a GOP leadership frozen in his glare—to reveal a president who can’t adapt, only blame, and a movement suddenly feeling less inevitable than it claims. Hosted on Acast. See acast.com/privacy for more information.

7 Marras 202540min