With President Donald Trump’s former reality show The Apprentice now streaming on Amazon Prime, politically engaged viewers from both sides of the aisle have taken note of a 2006 episode featuring Sen. Chuck Schumer, D-NY—now one of Trump’s fiercest critics—offering glowing praise for the future president.
In Season 5, Episode 8, contestants were given a typical challenge, with the winners earning a trip to Washington, DC, for breakfast with Sen. Schumer. During the meeting at the historic Hay-Adams Hotel, Schumer compared his own background to Trump’s and spoke admiringly of the businessman, telling the group he had always believed Trump “was going to go places.”
“I was born in Brooklyn, the same place where Donald Trump’s family comes from,” Schumer recalled during the conversation.
“His father, and my grandfather, were builders together in Brooklyn.”
“Wow!?” one contestant exclaimed. “Really?” another asked in surprise.
“Yeah!” Schumer replied to the group.
The show then cut to a segment of Schumer praising Trump as a standout in the business world.
“Even when [Trump] was much younger, you could tell he was going to go places,” Schumer said. A contestant’s voice-over followed, noting that “Sen. Schumer and Mr. Trump are good friends.”
Despite the seemingly warm remarks made in the 2006 episode of The Apprentice, Schumer clarified a decade later. In a 2016 interview with Politico ahead of Trump’s presidency, the New York Democrat stated, “[Trump] was not my friend.”
Donald Trump attends the red carpet event for “Celebrity Apprentice” at Trump Tower in New York City on February 3, 2015.
Schumer later characterized his relationship with Trump as merely a “casual acquaintance.”
“Donald Trump is a lawless, angry man,” Schumer said in an interview last month. He also took to social media earlier this month, writing, “The fact that The Apprentice President Donald ‘You’re Fired’ Trump is refusing to hold people accountable just shows how weak he is.”
In light of Schumer’s current harsh stance toward Trump, Michigan State GOP Senator Aric Nesbitt, the Michigan Senate’s minority leader, commented on the resurfaced Apprentice clip by posting, “How things change…”
And it’s not just Republicans joining in.
“As Schumer sells out our Constitution and democracy, you just gotta watch this clip of him sucking up to Trump on an episode of The Apprentice,” wrote former Rhode Island Democratic legislator Aaron Regunberg. “What a world-class slug of a man.”
Trump in a March 2008 episode of Celebrity Apprentice.
Just before taking office for his first term, Trump was asked by MSNBC’s Joe Scarborough and Mika Brzezinski whether he believed he could work with Democratic leaders in Congress, including Sen. Chuck Schumer. At the time, Trump struck an optimistic tone, saying he thought he would “get along well with Chuck Schumer.”
“I was always very good with Schumer. I was close to Schumer in many ways,” he said.
Since then, however, Trump’s tone toward Schumer has shifted significantly, with their relationship growing increasingly adversarial as they clash over the political battles dominating Washington week to week.
More recently, Trump criticized Schumer for what he described as a lack of support for the Jewish community amid a surge in antisemitism on college campuses following Hamas’ October 7, 2023 attacks on Israeli civilians. Notably, Schumer himself is Jewish.
Trump in a 2006 episode of The Apprentice.
“Schumer is a Palestinian, as far as I’m concerned,” Trump told reporters from the Oval Office last month. “He’s become a Palestinian. He used to be Jewish. He’s not Jewish anymore.”
Trump’s remarks echoed similar statements he made during his most recent presidential campaign, in which he controversially labeled Schumer a “proud member of Hamas.”
Schumer isn’t the only public figure who once praised Trump before turning into a political adversary. In a 1988 interview, Oprah Winfrey appeared struck by America’s “fascination” with Trump, even calling him a “folk hero” due to his widespread popularity.
Likewise, music mogul and Def Jam co-founder Russell Simmons once spoke favorably about Trump prior to his political career, describing him as “very nice” and noting how supportive he had been toward Simmons’ family, according to media reports.
Nevertheless, after the politically charged violence in Charlottesville during Trump’s first term, Simmons publicly criticized his former “friend,” accusing him of becoming a “great divider” and a “destroyer of the environment and … everything we as Americans have fought so hard to call ours.”
Fox News Digital contacted Schumer’s office for comment but did not receive a response by the time of publication.
