Chucky Schumer's gushing praise of Trump goes viral in throwback Apprentice clip he wishes was lost

Before he stood in staunch opposition to President Donald Trump, Sen. Chuck Schumer (D-NY) praised the businessman.

Amazon Prime’s decision to stream The Apprentice has resulted in political fans of the president pointing out a moment featuring Schumer, who had nothing but nice things to say about the future Oval Office resident.

Season 5, Episode 8 from 2006, long before Trump expressed serious political ambitions, saw contestants vying for a chance to eat breakfast with Schumer in Washington D.C. While eating breakfast with the contest winners, Schumer compared his family to that of the Trump family and praised the young business man as someone who “was going to go places.”

“I was born in Brooklyn, the same place where Donald Trump’s family comes from,” Schumer gushed.

“Wow!” a contestant said.

“Really?” asked another.

“Yeah!” the politician responded enthusiastically.

“Even when [Trump] was much younger, you knew that he was going to go places,” said Schumer before a pre-recorded voice-over reinforced that the politician and Trump were “good friends.”

anyone else watching “the apprentice” on amazon prime right now? in season 5 episode 8 (2006), apparently, donald trump considered senator chuck schumer a “friend.” i wonder what he’d say nowadays… pic.twitter.com/y6K6b4UvWn

— cyn ✨ (@cyn_dogelover) April 7, 2025

Many also don’t know that Chuck Schumer used to be good friends with Trump even appearing in The Apprentice, and that their fathers were also good friends growing up together in Brooklyn. https://t.co/6RsZcDUvko pic.twitter.com/pjsvFJA9UU

— UKNeil (@UKNeil79) April 4, 2025

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