Jack Schlossberg Reveals Reason Behind His Controversial Social Media Posts - E! Online
After months of sharing eyebrow-raising social media posts, Jack Schlossberg explained how his now-deactivated online presence was a political strategy.
Watch : Jack Schlossberg Shares NSFW Comment About His Grandma Jackie Kennedy & Usha Vance
Jack Schlossberg had a purpose behind his eyebrow-raising posts.
Before the grandson of President John F. Kennedy and Jackie Kennedy Onassis suddenly deactivated his social media accounts, he saw his many eyebrow-raising posts as a way to prove a point on what political messaging reaches people.
"I think that the internet is a place where it's difficult to break through," Jack explained on the Feb. 10 episode of the Blueprint with Jen Psaki podcast, which was recorded in January, "especially if you're not saying something that's controversial, or at least, somehow unexpected. I think that Democrats play that game not as well as we could."
Indeed, his posts were controversial, to say the least. For instance, the 32-year-old had asked social media users to compare the attractiveness of his grandmother and Vice President JD Vance's wife Usha Vance. He even agreed that his comments were "creepy" and "weird."
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Jack Schlossberg Reveals His Family's Reaction to His "Crazy" Social Media Videos
"I use my judgment to make posts that I think are funny or silly but have a purpose," he explained, "to make you think 'That guy's crazy. Why is he talking about his own family that way?' Then, you get all these retweets and quotes and everybody flips out about it. I think that that's the game that the other side has been playing really well, which is flipping people out and getting a reaction."Â
As Jackâwho is the youngest of Caroline Kennedy and Edwin Schlossberg's three kidsâput it, getting that attention is "almost half the battle."
One of his most confusing stunts was claiming to be Justin Baldoni's lawyer amid the actor's ongoing lawsuit with It Ends With Us costar Blake Lively. And he's now setting the record straight on what prompted the postsâwhich caught the attention of Baldoni's actual attorneys.Â
"It just came to me one night," Jack explained. "I see everybody arguing online about Justin Baldoni and Blake Lively, two people that otherwise I don't know anything about or have much invested in. I saw the entire country, seemingly, the entire internet, flipping out over this while I was focused on the change of administration and all the serious things that were going on."
MANDEL NGAN/AFP via Getty Images
"Our culture is obsessed with certain things," he continued. "Some are more important than others, you might say. How do you inject yourself and shine a light on that in a way that is totally out of the box?"
Although Jack has a law degree, he was shocked that anyone believed it. Despite the onslaught of coverage about his stunt was scary at first, the Vogue political correspondent knew that the controversy would eventually dissipate.
"I knew no one's going to remember this in a week," he said. "Everyone's going to forget about it because they've forgotten about a lot of way more serious things. At first, I was freaked out because everyone was mad. Then, once people started to understand it was a joke or that it was satire, I think people started to understand the game I was playing."
However, Jack's strategy also required different tones for other messages.
"Not every post is going to be hilarious or risky in some way," he noted. "Some of them have to be serious and boring, but they can't all be serious and boring. It's very important to switch it up and to take risks because that's not only entertaining for me as I laugh and post it on my phone but also a good way to signal to people that you're willing to either fight for them or speak your own mind."
Especially, he emphasized, "if you're willing to say something that other people might not get or you know might engender a reaction that some people don't like."Â
The interview, conducted the day after President Donald Trump's inauguration, was posted four days after Jack unexpectedly deactivated all of his social media accounts.Â
"I'm sorry to everyone I hurt," he wrote Feb. 6. "I was wrong. I'm deleting all my social media. Forever. It's been fun. Thanks anyways everyone."
Read on for a breakdown of the sprawling Kennedy family tree.
Everett/Shutterstock
Joseph P. Kennedy and Rose Kennedy
Joseph Patrick "Joe" Kennedy married Rose Elizabeth Fitzgerald on Oct. 7, 1914.
Bachrach/Getty Images
By 1932, they had nine children together: Joseph P. Kennedy Jr., John F. Kennedy, Rosemary Kennedy, Kathleen Kennedy, Eunice Kennedy, Patricia Kennedy, Robert F. Kennedy, Jean Kennedy and Edward Kennedy.
Keystone-France/Gamma-Keystone via Getty Images
Joseph P. Kennedy Jr.
Born July 25, 1915, Joe Jr. was going to be president, as far as his father was concerned.
He was a delegate to the 1940 Democratic National Convention and planned to run for Congress after he got out of the Navy. But the 29-year-old and his co-pilot Wilford John Willy were killed Aug. 12, 1944, when explosives they were carrying detonated prematurely while on a bombing run that was part of Operation Aphrodite.
Neither pilot's body was ever recovered and their names are among those on the Tablets of the Missing at the Cambridge American Cemetery and Memorial honoring casualties of World War II.
Mikki Ansin/Getty Images
John F. Kennedy
It was John, born May 29, 1917, who made it to Congress, then became a U.S. senator and ultimately was elected president in 1960.
He married Jacqueline Bouvier on Sept. 12, 1953, and they welcomed daughter Caroline Kennedy on Nov. 27, 1957, and son John F. Kennedy Jr. on Nov. 25, 1960.Â
A daughter, Arabella, was stillborn in 1956 and son Patrick, born prematurely on Aug. 7, 1963, lived for only 39 hours.
JFK was assassinated on Nov. 22, 1963, one of the defining events of the 20th century.
Tatiana, Jack, Rose, Edwin, Caroline (Clodagh Kilcoyne/Getty Images)
Caroline Kennedy
Caroline, the U.S. ambassador to Japan during the Obama administration and to Australia for the Biden administration, married Edwin "Ed" Schlossberg in 1986.
They share daughters Rose Kennedy Schlossberg (born June 25, 1988) and Tatiana Kennedy Schlossberg (May 5, 1990) and son John "Jack" Bouvier Kennedy Schlossberg (Jan. 19, 1993).
TV producer Rose went to Harvard like her mom and married restaurateur Rory McAuliffe in 2022.
Tatianaâa journalist who didn't know at the time that her 2014 New York Times article about a dead bear being found in Central Park involved her cousin RFK Jr.âgraduated from Yale and married college sweetheart George Moran in 2017. They welcomed a son, Edwin Jr., in 2022.
Jackâa Yale alum, graduate of Harvard's JD/MBA program and quite the hoot on social mediaâspoke at the 2024 DNC Convention and is a political correspondent for Vogue.
Justin Ide
John F. Kennedy Jr.
The former first son, named People's Sexiest Man Alive in 1988, was considered one of the most eligible bachelors on the planet before he married Calvin Klein publicist Carolyn Bessette on Sept. 21, 1996.
In a shattering twist of fate for his oft-grieving family, JFK Jr. died young like his father, his potential snuffed out when he was killed, along with Carolyn and her sister Lauren Bessette, in a plane crash on July 16, 1999.
Keystone/Getty Images
Rosemary Kennedy
Rosemary (at right, with sister Kathleen and mom Rose) was born Sept. 13, 1918.
While she attended a special boarding school for students with learning difficulties, Rosemary had behavioral issues that led to her father's decision to have her undergo a prefrontal lobotomy when she was 23.
Rosemary emerged from the experimental procedureâwhich was touted as a potential cure for mental illness and Joe did hope it would help herâseverely disabled and spent the rest of her life (she lived till Jan. 7, 2005) institutionalized.
"All along I had continued to believe that she could have lived her life as a Kennedy girl, just a little slower," Rose told historian Doris Kearns Goodwin years later. "But then it was all gone in a matter of minutes."
Bettmann Archive/Getty Images
Kathleen "Kick" Kennedy
Born Feb. 20, 1920, Kathleen got a kick out of life, hence her jaunty nickname.
She married William Cavendish, the Marquess of Hartington, in a civil ceremony in London on May 6, 1944âagainst her mother's wishes, as her beloved wasn't Catholic, so the bride's big brother Joe Jr. was the only member of her family who attended the wedding.
A month later, William, a major in the British Army, was killed by a sniper in Belgium.
She remained in England and fell for still-married William Wentworth-Fitzwilliam, 8th Earl Fitzwilliam. Before he could secure a divorce, they both died when the plane carrying them to the French Riviera crashed on May 13, 1948.
Bettmann
Eunice Kennedy Shriver
Eunice was born July 10, 1921.
The devoted philanthropist and founder of the Special Olympics married Robert Sargent Shriver Jr. on May 23, 1953.
Their had five childrenâRobert "Bobby" Shriver III (born April 28, 1954), Maria Shriver (Nov. 6, 1955), Timothy (Aug. 29, 1959), Mark (Feb. 17, 1964) and Anthony (July 20, 1965).
When she died at 88, Eunice had 19 grandchildren, including Maria's four kids with now-ex-husband Arnold Schwarzenegger:Â Katherine (born Dec. 13, 1989), Patrick (Sept. 18, 1993), Christina (July 23, 1991) and Christopher (Sept. 27, 1997).
Everett/Shutterstock
Robert F. Kennedy
The son known familiarly to the whole country as Bobby Kennedy married Ethel Skakel on June 17, 1950.
They went on to have 11 children: Kathleen, Joseph II, Robert Jr., David, Courtney, Michael, Kerry, Christopher, Maxwell, Douglas and Rory.
Ethel was pregnant with Rory when Bobby was fatally shot on June 6, 1968, shortly after winning the California Democratic primary.
David Kennedy died of a drug overdose on April 25, 1984, at the age of 28. Michael Kennedy was killed on Dec. 31, 1997, when he slammed into a tree while on skis and simultaneously tossing a football around during a family trip to Aspen, Colo. The 37-year-old shared three children with wife Victoria Gifford.
Her husband died when their eldest child was only 16, but Ethel Kennedy went on to be a grandmother of 34. Two of her grandchildren have died: Courtney and husband Paul Hill's daughter Saoirse Hill, 22, in 2019 of an accidental drug overdose and Kathleen and husband David Townsend's daughter Maeve Kennedy McKean, 40, in a 2020 canoeing accident.
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Robert F. Kennedy Jr.
RFK Jr., born Jan. 17, 1954, is a thrice-married father of six.
He shares son Robert Francis "Bobby" Kennedy III (born 1984) and daughter Kathleen "Kick" Kennedy (born 1988) with first wife Emily Black.
They divorced in 1994 after 12 years of marriage.
Amaryllis Fox/Instagram
Robert F. Kennedy III
RFK III has been married to CIA analyst turned author and TV host Amaryllis Fox since 2017.
They share daughter Bobby (born Jan. 7, 2019) and son Cassius Watts Thoreau Kennedy (Aug. 30, 2021), as well as Amaryllis' daughter Zoë from a previous relationship.
Â
Andrew Toth/Getty Images
Kick Kennedy
"I like to say life is just a collection of experiencesâsome good, some badâand the more you have the better," the Stanford grad told Town & Country in 2012.
And merely knowing Ben Affleck "in passing," as a source put it, brought Kick Kennedy to the top of the trending bar in August 2024 days after Jennifer Lopez filed for divorce from the actor.
Affleck's rep was quick to shut down romance speculation, telling E! News, "Everything about him and Kick is untrue."
So nothing about being a Kennedy had really changed in a decade. Or a century.
"People ask me, 'What's it like to be a Kennedy?'" she told T&C. "Maybe it's just the temperature of the water, but I'm just like, 'I have no idea.' When I see my face or name in the tabloids, I get a knot in my stomach. It's just not meâit's reading something that's not real."
But she did feel a kinship with the great aunt she was named for, who died two years before her father was born.
"It's funny how similar we are," Kick mused. "She was fun and social and a performer in many ways."
Stewart Cook/Shutterstock
RFK Jr. married Mary Richardson in 1994 and they went on to have four children: Conor Richardson Kennedy (born July 25 ,1994), Kyra LeMoyne Kennedy (Aug. 22, 1995), William Finbar "Finn" Kennedy (Nov. 8, 1997) and Aidan Caohman Vieques Kennedy (July 13, 2001).
The couple were legally separated when Mary died by suicide in 2012.
Rob Latour/Variety/Penske Media via Getty Images
Father and sons: Conor, Aidan and RFK III.
Axelle/Bauer-Griffin/FilmMagic
Conor Kennedy
Conor has maintained a fairly low profile, high-profile activism and other exploits aside, since rocketing to fame as an 18-year-old Harvard student and happened to bring Taylor Swift home to meet the family.
Their romance only lasted a few months, and Conor went on to grow up and graduate from Georgetown Law School. But, the headlines were made.
"Taylor Swift's ex Conor Kennedy" is now engaged to singer Giulia Be.
Thomas Razzano/BFA.com/Shutterstock
Kyra Kennedy
Kyra, a regular among the high-fashion set, lives in Milan.
She said in an Aug. 27, 2024, video posted in partnership with Elle and Bvlgari that she's working on a project in memory of her late mother.
"Have I experienced a rebirth in my life?" she asks in the clip. "Yes, I definitely have. As a little girl, I was one person. And when I became a young adult, I did a complete 180."
Matt Baron/BEI/Shutterstock
RFK Jr. married Curb Your Enthusiasm star Cheryl Hines in 2014.
The actress shares daughter Catherine Young (born March 8, 2004) with ex-husband Paul Young.Â
Kick Kennedy/Instagram
Modern Family
In wishing her dad a happy Father's Day in 2018, Kick wrote on Instagram, "Thanks for giving me all these wacky brothers and sisters!"
Mike Coppola/Getty Images for 2022 Robert F. Kennedy Human Rights Ripple of Hope Gala
Kerry Kennedy
Ethel and RFK's seventh child shares three daughtersâtwins Mariah Kennedy-Cuomo and Cara Kennedy Cuomo (born in 1995) and Michaela Kennedy-Cuomo (born in 1997)âwith ex-husband Andrew Cuomo.
Kerry and Andrew, who was governor of New York from 2011 to 2021, married in 1990 and separated in 2003 before divorcing in 2005.
Ron Galella/Ron Galella Collection via Getty Images
Edward "Ted" Kennedy
Sen. Ted Kennedy, more scandalous than 90 percent of his family put together, shared three children with first wife Joan Bennett: Kara Kennedy (born Feb. 27, 1960), Edward Kennedy Jr. (Sept. 26, 1961) and Patrick Kennedy IIÂ (July 14, 1967).
He and Joan divorced in 1982 after 24 years of marriage and he wed Victoria Reggie in 1992.
Kara suffered a fatal heart attack on Sept. 16, 2011, two years after her father died.
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