A resurfaced segment from Donald Trump’s former television show, “The Apprentice,” is generating considerable discussion given the current political climate. The episode, broadcast as part of a streaming offering on Amazon Prime last month, features then-Senator Chuck Schumer, now a prominent critic of President Trump, expressing admiration for the president’s business acumen during a 2006 appearance.
During Season 5, Episode 8, Senator Schumer participated in a challenge designed to connect rising talent with influential figures. The prize for winning was a trip to Washington D.C., where contestants would meet with Schumer for breakfast. The conversation unfolded at the Hay-Adams hotel, and Schumer recounted his personal connection to Trump, noting their shared Brooklyn origins and his father’s professional relationship with Trump’s family – “builders together in Brooklyn.”
Contestants reacted with surprise and curiosity, prompting Schumer to declare, “I was born in Brooklyn, the same place where Donald Trump’s family comes from. His father, and my grandfather, were builders together in Brooklyn.” A voice-over from one of the present contestants confirmed that Schumer and Trump were “good friends” at the time.
However, this earlier sentiment sharply contrasts with Schumer’s current stance. In 2016, ahead of Trump’s first term, Schumer described their relationship as “a casual acquaintance,” and in subsequent statements, he has been exceptionally critical of the president. “Donald Trump is a lawless, angry man,” Schumer stated recently, adding that Trump’s actions demonstrate weakness. “How things change…” remarked Michigan State GOP Sen. Aric Nesbitt, commenting on the unearthed clip.
The situation highlights a shifting dynamic within American politics. Former Democratic Rhode Island legislator Aaron Regunberg commented, “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.” Interestingly, shortly before taking office, Trump suggested he would have a positive relationship with Schumer, stating, “I was always very good with Schumer. I was close to Schumer in many ways,” during an interview with MSNBC’s Joe Scarborough and Mika Brzezinski.
Despite this initial optimism, Trump’s rhetoric has intensified over time. Recently, he criticized Schumer regarding his perceived stance on antisemitism within the context of rising concerns about hate speech on college campuses following the October 7th attacks in Israel. Trump’s statements mirrored sentiments from his presidential campaign when he referred to Schumer as a “proud member of Hamas.”
The story also echoes instances involving other prominent figures who initially praised Trump before later becoming political adversaries. In 1988, Oprah Winfrey expressed her admiration for Trump and described him as a “folk hero,” while music producer Russell Simmons called him “very nice” and noted his support for Simmons’ family. However, after the events in Charlottesville during Trump’s first term, Simmons sharply criticized the then-president.
Schumer’s office did not respond to requests for comment on this matter.
