In a candid interview that blended family legacy with pointed political commentary, Jack Schlossberg, grandson of President John F. Kennedy, outlined a stark path for President Donald Trump to earn the Kennedy family's esteemed Profile in Courage Award. Speaking on MSNBC's MS Now on Sunday, March 22, the 33-year-old Schlossberg delivered what appeared to be a sarcastic blueprint during a discussion promoting the award's upcoming ceremony.
The Profile in Courage Award, inspired by JFK's 1956 Pulitzer Prize-winning book of the same name, recognizes individuals who exhibit moral bravery in public life. This year's recipients, announced for the ceremony on May 31 at the John F. Kennedy Presidential Library and Museum in Boston, Massachusetts, include Federal Reserve Chair Jerome Powell and the people of Minneapolis. Powell is being honored for "protecting the independence of the Federal Reserve," while the Minneapolis community is recognized for "risking their lives to protect their neighbors and immigrant community members from an unprecedented federal law enforcement operation."
Schlossberg, who serves on the award's selection committee as a Kennedy heir, was pressed by host Alex Wagner on what Trump would need to do to join the ranks of past winners. His response was laced with irony: "If President Trump admitted to the many crimes and the grift that he has committed while president in office; stepped down and handed over the power of the presidency to somebody responsible, and not somebody in his own Cabinet; if he came forward with all the true reasons behind his pick for RFK Jr. as secretary of health and human services — and who is paying for the words that are coming out of RFK Jr.'s mouth — then maybe that would be some kind of courage that we would consider."
"To be honest, I don’t think he’s in the running anytime soon," Schlossberg joked, underscoring the improbability of such a scenario.
The White House has not immediately responded to requests for comment on Schlossberg's remarks, according to Us Weekly, which first reported the interview. Trump's second term, which began in January 2025, has already seen tensions with the Kennedy family escalate over his administration's decisions involving institutions tied to the late president's name.
One flashpoint has been Trump's self-appointment as chairman of Washington, D.C.'s Kennedy Center for the Performing Arts, followed by his announcement to rename it the "Donald J. Trump and the John F. Kennedy Memorial Center for the Performing Arts." In December 2025, the center is set to close for a two-year restoration project, a move Trump touted as a revitalization effort but which has drawn sharp rebukes from Kennedys.
Maria Shriver, daughter of JFK's sister Eunice Kennedy Shriver and a prominent journalist in her own right, voiced her disapproval on Instagram last December. "Adding your name to a memorial already named in honor of a great man doesn’t make you a great man. Quite the contrary," she wrote. "Putting your name on top of someone else’s doesn’t mean that people will speak of you in the same breath as the other man. Putting your name above another man’s name on his existing memorial… What is that about? Truly? What’s that about?"
Shriver's post captured a broader sentiment within the Kennedy clan, who have long viewed the center as a tribute to JFK's cultural legacy. The facility, established by Congress in 1964 and opened in 1971, has hosted countless performances and events honoring American arts, with the Kennedy name symbolizing a commitment to public service and excellence.
Despite the family's criticisms, not all Kennedys have aligned against Trump. Robert F. Kennedy Jr., JFK's nephew and now U.S. Secretary of Health and Human Services in the Trump administration, has distanced himself from the feud. In a January interview with CBS News, RFK Jr., 72, acknowledged the family's upset but prioritized his role. "Of course. I understand it, but I have bigger fish to fry," he said, referring to pressing health policy issues under his purview.
RFK Jr.'s appointment, confirmed by the Senate in early 2025, has been controversial, particularly given his history of vaccine skepticism and environmental activism. Schlossberg's MSNBC comments alluded to undisclosed influences behind the nomination, though he provided no specifics. The secretary's office has not elaborated on those claims.
The Profile in Courage Award itself has a track record of bipartisan selections, reflecting the Kennedy family's tradition of transcending party lines in recognizing integrity. Recent honorees include former Vice President Mike Pence in 2025 for his role in certifying the 2020 election results, and former Republican Congresswoman Liz Cheney in 2022 for her outspoken criticism of Trump's election interference efforts. Earlier winners span Democrats like John McCain and Republicans like John Lewis, showcasing the award's nonpartisan ethos.
Schlossberg's appearance on MS Now came amid his own foray into politics. In November 2025, he announced his candidacy for New York's 12th congressional district, a seat being vacated by retiring Democratic Rep. Jerry Nadler. The East Side Manhattan district, which includes parts of Midtown and the Upper East Side, is a Democratic stronghold, but Schlossberg has emphasized his family's legacy of public service in his campaign launch.
"As JFK’s grandson, I’ve seen firsthand the impact of courageous leadership," Schlossberg said in his announcement, according to campaign statements. His run adds to a string of Kennedy family members entering electoral politics, from his late mother, Caroline Kennedy, who served as U.S. ambassador to Japan, to cousins like Joe Kennedy III, who held a Massachusetts congressional seat until 2021.
The Kennedy-Trump rift underscores deeper divides in American politics, where personal legacies intersect with national institutions. Trump's renaming of the Kennedy Center, for instance, follows his pattern of branding public spaces, similar to proposals for other federal sites during his first term. Critics, including historians, argue it dilutes historical significance, while supporters see it as a bold assertion of leadership.
Meanwhile, the Profile in Courage Award ceremony in Boston is expected to draw dignitaries from across the political spectrum, highlighting Powell's tenure at the Fed amid economic turbulence. The Minneapolis honor recognizes community efforts during a 2024 federal operation targeting immigration enforcement, where locals reportedly formed human chains to shield vulnerable residents, according to local reports.
As Schlossberg's congressional bid gains traction, his comments on Trump may resonate with voters seeking a fresh Kennedy voice. Polls in the district show a competitive primary, with Schlossberg positioning himself as a bridge between progressive ideals and pragmatic governance. Whether his barbs at the president boost or hinder his campaign remains to be seen.
Looking ahead, the Kennedy family's influence persists in shaping public discourse on courage and accountability. With RFK Jr. navigating his cabinet role and Schlossberg eyeing Congress, the dynasty's next chapter could redefine its stance in a polarized era. The White House's silence on the latest critique leaves open questions about potential responses, as Trump's administration pushes forward on its agenda.
In Boston, preparations for the May 31 event continue, a reminder of JFK's enduring call for moral fortitude in leadership. As one Kennedy heir jests about the unlikelihood of Trump's inclusion, the award stands as a beacon amid ongoing political tempests.