Schumer's Old 'Apprentice' Praise for Trump Goes Viral: From 'Going to Go Places' to Political Frenemies

Sen. Chuck Schumer's unexpectedly glowing words for Donald Trump from a 2006 episode of "The Apprentice" have resurfaced, setting the internet ablaze with a dose of political déjà vu. Thanks to Amazon Prime streaming the reality show, viewers have dug up a vintage clip where Schumer—now a fierce Trump critic—gushes about the former president's business acumen and predicts his bright future.

Back in Season 5, Episode 8, "The Apprentice" contestants got to have breakfast with Schumer at the Hay-Adams Hotel in Washington, D.C. Instead of the trademark political sparring we see today, Schumer played up his Brooklyn roots, highlighting that his grandfather and Trump’s father were fellow builders. He told the group, "Even when [Trump] was much younger, you knew that he was going to go places." The room responded with genuine surprise—if only they had a crystal ball for what was to come.

A contestant chimed in, recalling, "Sen. Schumer and Mr. Trump are good friends." My, how times change. Fast-forward to 2016, and Schumer categorically denied any real friendship with Trump, calling their relationship a "casual acquaintance." By 2025, the gloves are off entirely—Schumer has labeled Trump "a lawless, angry man," while Trump has lobbed back barbs, even questioning Schumer’s Jewish identity in the wake of rising antisemitism debates.

Schumer's earlier praise has now become political ammo for both sides. Michigan GOP Sen. Aric Nesbitt couldn’t resist a jab, posting "How things change…" with the old footage. Former Democratic Rhode Island legislator Aaron Regunberg piled on, sarcastically calling Schumer a "world class slug of a man" for his on-screen deference to Trump.

It’s not just Schumer who did an about-face. The article reminds us Oprah Winfrey once called Trump a "folk hero," and even music producer Russell Simmons had kind words before becoming sharply critical during Trump’s presidency. Apparently, in American politics, yesterday’s handshake is today’s headline.

When asked before his first term about his rapport with Democrats like Schumer, Trump sounded optimistic, saying he thought he’d "be able to get along well." But as the years rolled on, both men dug in their heels, trading increasingly pointed criticisms over everything from leadership to responses to antisemitism.

Schumer’s office was contacted for comment on his "Apprentice" moment, but no response was given in time for publication. If we’ve learned anything from this viral blast from the past, it’s that the political friend zone is a very temporary place.