David Letterman and his wife, Regina Lasko, made an appearance at the John F. Kennedy Profile in Courage Award ceremony in Boston on May 31. Their attendance was marked by a heartfelt show of support for their close friend, Caroline Kennedy, who has been navigating a difficult time following the recent death of her daughter, Tatiana Schlossberg.
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Tatiana, a journalist and author, passed away in December 2025 after a courageous battle with acute myeloid leukaemia, a type of blood cancer. She was only 35 years old and had given birth to her second child just a year earlier. The couple spoke candidly with PEOPLE as they arrived at the JFK Presidential Library and Museum, providing insights into how Caroline has been coping with her family’s tragic loss.
Commenting on the resilience of the Kennedy family, Lasko conveyed her belief that they are managing as well as could be expected under the circumstances. Letterman, reflecting on their steadiness, remarked, “If I had to describe the Kennedys over the past five months, one word comes to mind: steady.” His sentiments highlighted the family’s characteristic strength during challenging times.
The couple had also joined Caroline and her family for Tatiana’s funeral in January, which was attended by a number of notable figures, including former President Joe Biden and former Secretary of State John Kerry. Their presence at these significant family moments points to the close-knit relationships that the Kennedys maintain with their friends and supporters.
Caroline Kennedy took to the stage at the recent award ceremony to pay tribute to her late daughter. In an emotional speech, she celebrated Tatiana’s life and her contributions, particularly her role on the board of the JFK Presidential Library. “Most of all, we remember Tatiana, who represented everything my parents stood for in her beautiful, amazing, and too-short life,” she expressed, her voice wavering with emotion as she fought back tears. The audience responded to her heartfelt words with a prolonged applause, acknowledging Tatiana’s impact on those who knew her.
Tatiana had previously penned a poignant essay for The New Yorker in November 2025, where she shared her reflections on life, motherhood, and her terminal diagnosis. In a deeply moving account, she spoke about her desire to be a good daughter and mother, revealing the heartbreaking realisation that her illness added another layer of tragedy to her family’s narrative.
During the ceremony, Caroline highlighted the bravery displayed by the recipients of this year’s award, including the people of the Twin Cities in Minnesota and Jerome Powell, the former Chair of the Federal Reserve. The awards were a recognition of their efforts in standing firm against immigration crackdowns during the previous administration.
Letterman, known for his sharp wit, made light of his admiration for the Federal Reserve before the event. He joked about his childhood fascination with the organisation and even mentioned his hope for a selfie with Powell, who has been a prominent figure in economic discussions involving interest rates and monetary policy.
Caroline Kennedy also took time to honour individuals who have faced hardship amidst political turmoil, including the residents of Minneapolis and St. Paul who took a stand against the influx of federal agents during immigration enforcement efforts. “It’s sad and cool and exciting that they’re being remembered and honoured because that state has been pummeled unnecessarily,” Letterman remarked about their courage.
The award ceremony not only served as a memorial for Tatiana Schlossberg but also as a platform for discussing the pressing social issues of the day. Caroline concluded her speech by recognising the immense difficulty of being a “profile in courage” and acknowledged the challenges faced by family members of those at the forefront of social justice movements.
As Letterman and Lasko mingled with attendees at the event, it was clear that their presence provided a layer of support and camaraderie for Caroline and her family. Through shared grief and the celebration of courage, the community surrounding the Kennedy legacy remains steadfast in its commitment to honouring the values and ideals that defined it.