It’s hard to rival Schumer’s hatred for the president. But that’s what makes these comments so surprising.
And Schumer was caught on a hot mic saying this insane thing about Donald Trump.
The recent streaming of President Donald Trump’s former reality TV show “The Apprentice” on Amazon Prime has sparked renewed interest among viewers, particularly those with a keen eye for political history. One episode, in particular, has captured attention for featuring Sen. Chuck Schumer, D-NY, now a vocal critic of Trump, warmly praising the then-business mogul during a 2006 breakfast scene.
In Season 5, Episode 8 of “The Apprentice,” aired nearly two decades ago, contestants competed in a challenge, with the winners earning a trip to Washington, DC, for a breakfast with Schumer at the prestigious Hay-Adams hotel.
Over the meal, Schumer drew personal connections to Trump, noting their shared Brooklyn roots. “I was born in Brooklyn, the same place where Donald Trump’s family comes from,” Schumer told the group. “His father, and my grandfather, were builders together in Brooklyn.”
The revelation prompted surprised reactions from contestants. “Wow!?” one exclaimed, while another asked, “Really?” Schumer confirmed with an enthusiastic “Yeah!” before going further, describing Trump as a business prodigy. “Even when [Trump] was much younger, you knew that he was going to go places,” Schumer said. A contestant’s voice-over reinforced the sentiment, noting that “Sen. Schumer and Mr. Trump are good friends.”
Fast forward to today, and the warmth of that 2006 exchange feels like a distant memory. Schumer’s stance on Trump has shifted dramatically. In 2016, as Trump prepared for his first term, Schumer downplayed their past, telling Politico that Trump “was not my friend” but rather a “casual acquaintance.”
More recently, Schumer’s criticism has sharpened. Last month, he called Trump “a lawless, angry man” in an interview, and in a social media post this month, he wrote, “The fact that The Apprentice President Donald ‘You’re Fired’ Trump is refusing to hold people accountable just shows how weak he is.”
The resurfaced “Apprentice” clip has not gone unnoticed, drawing commentary from across the political spectrum. Michigan State GOP Sen. Aric Nesbitt, the Senate minority leader, highlighted the episode with a wry remark: “How things change…”
Meanwhile, former Democratic Rhode Island legislator Aaron Regunberg took a harsher tone, stating, “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. What a world class slug of a man.”
Trump, too, has reflected on their relationship over the years. Before his first term, in an interview with MSNBC’s Joe Scarborough and Mika Brzezinski, he expressed optimism about working with Schumer, saying, “I was always very good with Schumer. I was close to Schumer in many ways.”
But as political battles have intensified, Trump’s rhetoric has grown pointed. Last month, he took aim at Schumer’s stance on issues tied to the Jewish community, particularly amid rising antisemitism following Hamas’ October 7, 2023, attacks on Israel.
“Schumer is a Palestinian, as far as I’m concerned,” Trump said from the Oval Office. “He’s become a Palestinian. He used to be Jewish. He’s not Jewish anymore.”
These remarks echo earlier campaign rhetoric where Trump labeled Schumer a “proud member of Hamas.”
Schumer isn’t the only public figure whose past praise for Trump has contrasted with later criticism. In a 1988 interview, Oprah Winfrey marveled at Americans’ “fascination” with Trump, calling him a “folk hero” for his popularity.
Similarly, music producer Russell Simmons, who co-founded Def Jam Records, once described Trump as “very nice” and supportive of his family.
However, after the 2017 Charlottesville violence, Simmons condemned Trump as a “great divider” and a “destroyer” of American values.
The evolving dynamic between Schumer and Trump, as captured in this “Apprentice” episode and their subsequent public clashes, reflects the complex interplay of personal ties and political divides.
What began as mutual admiration has transformed into a high-stakes rivalry, emblematic of the shifting allegiances that shape Washington’s landscape.
Stay tuned to The Federalist Wire.
