Late-Night Roast of the Century: Colbert’s “Tooth and Cankle” Jab at Trump’s Epstein Files Flip-Flop Has Everyone Cracking Up.

In the high-stakes poker game of American politics, where bluffs are currency and fold means fiasco, Donald Trump just got called out in the most hilariously brutal way imaginable. On Thursday night’s The Late Show with Stephen Colbert, the host dove headfirst into the bombshell bill forcing the release of Jeffrey Epstein’s long-buried files – a bipartisan steamroller that Trump, after months of desperate resistance, reluctantly signed into law. But Colbert, ever the master wordsmith with a scalpel for a tongue, couldn’t let the moment pass without a zinger that has the internet in stitches: “After months of Trump fighting tooth and cankle to hold back the Republican Party from doing the right thing, he just went ahead and gave up and signed the bill to release the Epstein files.”

Tooth and cankle? For the uninitiated, it’s Colbert’s razor-sharp riff on the idiom “tooth and nail” – twisted to mock Trump’s infamous “cankles” (those famously fleshy ankles he’s been ribbed about since his Apprentice days). Paired with a graphic of Trump mid-stride in ill-fitting heels (okay, maybe not, but the visual in our heads is gold), the line landed like a perfectly timed pratfall, eliciting howls from the Ed Sullivan Theater crowd and a torrent of memes across social media. By Friday morning, #ToothAndCankle was trending with over 300,000 posts, featuring everything from Photoshopped Trump portraits with chompers for toes to fan edits syncing the joke to Baby Shark. “Colbert just turned Trump’s ankles into a national punchline,” one viewer tweeted. “Epstein files? Who cares – I’m dying over the cankles.”

The context? It’s pure political theater at its most absurd. Last week, Congress – in a rare show of unity that crossed party lines like a bipartisan conga line – voted nearly unanimously (428-3 in the House, 98-2 in the Senate) to compel the Justice Department to unseal and release all remaining Epstein documents within 30 days. The files, a Pandora’s box of depositions, flight logs, and victim statements from the late financier’s sex-trafficking empire, have tantalized conspiracy theorists and truth-seekers alike since Epstein’s 2019 jailhouse “suicide.” Names like Bill Clinton, Prince Andrew, and – yes – Donald Trump have swirled in the periphery for years, with Trump’s Mar-a-Lago ties to Epstein fueling endless speculation. Trump, who once called Epstein a “terrific guy” before distancing himself post-arrest, spent the lead-up months lobbying Republicans to kill the bill, dismissing it as a “Democrat hoax” designed to “smear” him ahead of his 2028 reelection whispers.

Enter Colbert, who framed the saga as Trump’s ultimate poker tell. “Even though Trump told Republicans to all vote for this, he was clearly furious that they did,” the host quipped, rolling footage of Trump’s frosty White House photo lid – a deliberate shutdown of cameras that screamed “guilty as charged.” “He signed it off camera, and he’ll sign anything on camera – executive orders, sneakers, lady parts, wall parts, a toddler.” Cue the montage: clips of Trump scribbling his Sharpie scrawl on everything from MAGA hats to that infamous Hurricane Dorian map, interspersed with absurd deepfakes of him autographing beach sand and fast-food wrappers. The punchline? “Trump is avoiding cameras. That’s like the Pillsbury doughboy avoiding nudity.” The audience lost it, and so did we – because in an era of endless spin, Colbert’s ability to deflate egos with dad-joke precision is a public service.

But beneath the laughs, this isn’t just fodder for monologue gold; it’s a seismic shift in the Trump narrative. The Epstein files’ impending dump – slated for mid-December – could unearth details that make Watergate look like a kiddie pool splash. Epstein’s infamous “Lolita Express” jet logs already list Trump seven times in the ’90s, and unsealed court docs from 2015 hinted at Mar-a-Lago as a recruiting ground for young women (though Trump has vehemently denied wrongdoing, claiming he banned Epstein from the club in 2007). Victims’ advocates, like those from the National Center for Missing & Exploited Children, hailed the bill as “long overdue justice,” while legal eagles predict a flood of civil suits and congressional hearings. Trump’s Truth Social meltdown the day after signing? A 1,200-word screed dismissing the files as “fake news from sleepy Joe’s basement,” complete with ALL CAPS rants about “DEEP STATE PEDOS” – which Colbert mock-texted as “Bro, TL;DR, just hit ‘haha’ emoji.”

Colbert wasn’t alone in the late-night pile-on. Over on Late Night with Seth Meyers, the host dubbed it “the greatest test yet of Trump’s nearly mystical ability to lie his way out of any problem.” Meyers replayed Trump’s flip-flop in slow-mo: from veto threats in October (“This witch hunt ends with me!”) to a grudging endorsement last week after GOP leaders like Mitch McConnell twisted arms behind closed doors. “It’s obvious why Trump fought so hard to stop this bill from passing,” Meyers deadpanned. “Because if there’s one thing Donald doesn’t want released, it’s files on a guy who knew all his secrets – and probably has the receipts.” Jimmy Kimmel, from his Hollywood perch, chimed in with a bit on Trump’s “cankle conniption,” joking that the president’s ankles “swelled up just thinking about those flight logs.” Even The Daily Show‘s guest host Ronny Chieng couldn’t resist: “Trump signed it off-camera? That’s not suspicious at all. Next, he’ll claim Epstein was his podiatrist.”

The ripple effects are already tsunami-sized. Wall Street jittered Friday, with Trump Media & Technology Group shares dipping 4% on fears of scandal fatigue. Pundits on CNN and MSNBC are booking every Epstein expert from Virginia Giuffre’s lawyers to forensic accountants, speculating on bombshells like redacted Black Book entries or video evidence from Little St. James island. Trump’s camp, predictably, is in damage control: a spokesperson called the bill “a nothingburger signed for national security,” while allies like Lindsey Graham floated defunding the DOJ if things get “too political.” On the flip side, Democrats like Elizabeth Warren are demanding expedited reviews, tweeting, “Transparency isn’t optional – it’s the law Trump just inked.”

For Colbert, though, the real win is cultural: turning a dark chapter into digestible satire. At 61, the former Strangers with Candy alum has evolved from ironic everyman to elder statesman of snark, using his CBS perch (now averaging 3.2 million nightly viewers) to bridge laughs and accountability. His Epstein segment – clocking in at seven minutes of monologue magic – spiked YouTube views to 2.5 million overnight, outpacing even his post-election specials. Fans adore how he threads the needle: savage without soulless, probing without preachy. “Stephen’s the therapist America needs,” one Reddit thread raved. “He calls out the crazy so we don’t have to.”

As Thanksgiving looms tomorrow, with families debating turkey over tariffs, Colbert’s cankle crack serves as a reminder: In Trump’s America 2.0, where tariffs jack up cranberry prices and tariffs on truth run even higher, humor is our secret weapon. Will the files torch Trump’s Teflon? Expose a web of elite enablers? Or fizzle into another footnote? Only time – and maybe a follow-up monologue – will tell. For now, pass the stuffing and the Schadenfreude. Because if Trump can fight tooth and cankle, we can laugh our way through the fallout.

One thing’s certain: Colbert’s got the last word – or at least the wittiest one. “If those files drop and Trump’s name isn’t on page one,” he signed off, “I’ll eat my bowtie. But if it is? Pass the salt – this drama’s just getting seasoned.”

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