David Letterman and Wife Regina Lasko Reveal How Kennedys Are Holding Up After Tatiana Schlossberg's Death (Exclusive)

Juliet Pennington, Joseph KonigMon, June 1, 2026 at 6:45 PM UTC

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Regina Lasko and David Letterman; Caroline Kennedy at the JFK Profile in Courage Award ceremony on May 31
Credit: Cindy Ord/WireImage; Mel Musto/Bloomberg via Getty -

David Letterman and his wife, Regina Lasko, attended the ceremony for the 2026 John F. Kennedy Profile in Courage Award in Boston on Sunday, May 31

They were there in part to support their friend Caroline Kennedy just months after her daughter Tatiana Schlossberg died

The couple spoke to PEOPLE and offered insight on how the Kennedy family is holding up after the loss of the 35-year-old journalist and author in December 2025

David Letterman and his wife, Regina Lasko, attended the ceremony for the 2026 John F. Kennedy Profile in Courage Award in Boston on Sunday, May 31, in part to support their friend Caroline Kennedy just months after her daughter Tatiana Schlossberg died.

As they arrived at the event at the JFK Presidential Library and Museum on Sunday night, Letterman and Lasko spoke with PEOPLE, offering insight on how Caroline and her family are holding up after the loss of the 35-year-old journalist and author in December to a fatal blood cancer.

Lasko, a friend of Caroline’s, told PEOPLE that the family is doing “as well as could be expected.”

Letterman shared that if he had to describe the Kennedys in the five months since Tatiana's death, one word comes to mind. “Steady — and unsurprisingly given who they are and what they are," the comedian said. "I would say steady.”

Letterman and Lasko, who dated for more than two decades before marrying in 2009, attended Tatiana's funeral in New York on Jan. 5 alongside Caroline; her husband, Ed Schlossberg; and Tatiana’s siblings, Rose and Jack Schlossberg. Other luminaries, including former President Joe Biden and former Secretary of State John Kerry, attended as well.

Tatiana was diagnosed with acute myeloid leukemia, a blood cancer, shortly after giving birth to her second child with husband, George Moran, in 2024.

At the award ceremony on Sunday, Caroline, 68, paid tribute to the work and life of her late daughter and honored George's parents, Garrett and Mary Moran, who were in attendance for the first time.

“Most of all, we remember Tatiana, who served on the board of this library and represented everything my parents stood for in her beautiful, amazing and too-short life,” she said as her voice wavered and she appeared to fight back tears.

The audience applauded Tatiana for nearly 20 seconds, prompting Caroline to quietly say, "Thank you."

Prince William, left, is welcomed by Caroline Kennedy, right, and her children Jack and Tatiana Schlossberg at the John F. Kennedy Presidential Library and Museum in Boston on Dec. 2, 2022.
Credit: ANGELA WEISS/AFP via Getty

In a devastating November 2025 essay for The New Yorker revealing her terminal diagnosis and reflecting on leaving behind her two young children, Tatiana wrote that for her "whole life, I have tried to be good" and, among other things, "protect my mother."

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"Now I have added a new tragedy to her life, to our family’s life, and there’s nothing I can do to stop it," Tatiana wrote, while also sharing the small joys she still was savoring, like her daughter stomping "around the house in bright-yellow rain boots, pretending to talk on my mother’s phone."

Letterman, a longtime late-night host, interviewed Caroline about JFK, her mother, Jacqueline Kennedy Onassis, and growing up as a Kennedy on The Late Show in 2011.

“I think one of the great things about history… is that it really brings generations together because people have heard their families, their parents, grandparents talk about this and talk about this kind of inspiration that my father represented,” Caroline told Letterman at the time, adding that she wished her children could have met their grandparents.

Caroline Kennedy gets a laugh from Late Show host David Letterman during her appearance on the Late Show with David Letterman on May 3, 2011.
Credit: John Paul Filo/CBS via Getty

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Tatiana’s 33-year-old brother, who is campaigning in a crowded Democratic primary for a Manhattan congressional seat, also helped his mother grant the award to its recipients at Sunday night’s ceremony: the people of the Twin Cities of Minnesota and former Federal Reserve Chair Jerome Powell.

Letterman joked with PEOPLE before the event that “I’m a big fan of the Fed. From the time I was a child, I just couldn’t get enough of the Fed,” teasing that he was hopeful to get a selfie with the professorial central banker who has clashed with President Donald Trump over interest rates and the minutiae of U.S. monetary policy.

As for the people of Minneapolis and St. Paul, who were being honored for standing up to the flood of federal agents into Minnesota as part of Trump’s immigration crackdown, Letterman said “it’s sad and cool and exciting that they’re being remembered and honored because that state has been pummeled unnecessarily.”

Jack Schlossberg, grandson of former US President John F. Kennedy, from left, Federal Reserve governor Jerome Powell, and former U.S. Ambassador Caroline Kennedy, JFK's daughter.
Credit: Mel Musto/Bloomberg via Getty

“They mobilized, organized, and refused to be terrorized by an overwhelming federal crackdown which sent 3,000 heavily armed ICE agents into their communities to arrest and deport citizens and non-citizens alike,” Caroline said as she presented the award named for her father.

Caroline also honored Renée Good and Alex Pretti, two Minneapolis residents and U.S. citizens who were killed by federal agents in January. Good’s father, brother and sister were also in attendance.

“It’s hard to be a profile in courage, but it is sometimes even harder to be their family member,” Caroline said.

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