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JFK Jr.'s Inner Circle Shares Rarely Seen Photos & Touching Memories

John F. Kennedy Jr. died on July 16, 1999, in a plane crash that also killed his wife and her sister. Here, friends remember the man behind the famous last name

By Liz McNeil 
 
Updated on November 25, 2022 11:05 AM
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01of 13

A Forever Bond

John F. Kennedy Jr.
SASHA CHERMAYEFF/AUGUST

John first met his dear friend Sasha Chermayeff at Andover, the elite boarding school he attended as a teenager. Pictured: John and Sasha in 1992.

"John always carried a lot of responsibility and weight," Chermayeff says. "I think he had his share of burdens. But in a manner that seemed fearless, he sought out a real life."

 
02of 13

Great Expectations

John F. Kennedy Jr.
SASHA CHERMAYEFF/AUGUST

"No one will ever live a life like John F. Kennedy Jr," says Gillon, a historian, author of America's Reluctant Prince and a friend of John's since John's time at Brown University.

"There's probably no one who's ever walked the earth that was the focus of media attention their entire life," says Gillon of John, seen here in 1978 at Andover.

 
03of 13

A Life of Promise

Memorial Day 1992John on Martha's Vineyard, MA.
SASHA CHERMAYEFF/AUGUST

"There's many layers to the tragedy of his death," Gillon says.

John, pictured on Martha's Vineyard in 1992, "had spent his life trying to figure out who he was and what he wanted to do," Gillon says. "And he finally figured it out in those last couple of years. He discovered that his calling was to go into politics."

 
04of 13

A Loving Heart

John F. Kennedy Jr.
SASHA CHERMAYEFF/AUGUST

John was the godson to Chermayeff's son Phineas. (They are pictured here in 1993.)

"Although there is pain and endless sorrow, I am always so glad to think of him, so glad I got to really know him and I feel blessed by that remarkable twist of fate," Chermayeff says.

 
05of 13

No Shirt, No Problem

1992John on the beach on Martha's Vineyard.
SASHA CHERMAYEFF/AUGUST

John (in 1992 on Martha's Vineyard) was often teased by pals about his love of showing off his body.

"He had all the physical attributes of a body builder," says Gillon, "but he was a really sensitive caring person inside."

 
06of 13

'Alive to the Fullest'

Labor Day 1998John & Philip (Sasha's husband) in Hyannis Port, MA.
SASHA CHERMAYEFF/AUGUST

John (here in 1998 in Hyannis Port, Massachusetts, with Phillip Howie, Chermayeff's husband) "was openhearted, compassionate, warm," Chermayeff says.

He was "alive to the fullest."

 
07of 13

Soaking Up the Sun

John F. Kennedy Jr.
SASHA CHERMAYEFF/AUGUST

John in the summer of 1993 on Martha's Vineyard with actress Daryl Hannah, whom he dated off and on for several years.

 
08of 13

Just John

John F. Kennedy Jr.
SASHA CHERMAYEFF/AUGUST

Raised in the spotlight, John carried his fame with natural ease, friends say. Here he is seen goofing off at a dinner party with Chermayeff (right) and her sister, Maro, in 1991.

But, says Gillon, "John did not just lead a charmed life. He led a complicated life."

 
09of 13

Carefree Memories

1988Sasha, John, Stuart Fullerton and Jenny Landey in New York City.
SASHA CHERMAYEFF/AUGUST

John, with Sasha (right) and a few friends in New York City in 1988.

 
10of 13

True Confidantes

JFK JR
SASHA CHERMAYEFF/AUGUST

"John did things with his male friends — ski trips, kayaking, and many travels — but he confided in his female friends, especially Sasha," says Gillon, who befriended John after he became John's teaching assistant in a history class John attended at Brown.

John (seen here with Chermayeff in 1988) "was also the best person to get advice from," Gillon says. "He had spent a lot of time analyzing himself and, in doing so, he had a better sense of other people."

 
11of 13

A Fond Regard

JFK JR
SASHA CHERMAYEFF/AUGUST

Chermayeff (here with John in 1991 at her birthday party) was close to both him and his wife, Carolyn Bessette Kennedy.

"John and Carolyn were wonderful people," she says. "They fell in love and had a stunning, dream-like wedding. I don't know what would have come to pass ... no one does."

 
12of 13

A Friend Remembers

JFK JR. and Carolyn
SASHA CHERMAYEFF

Chermayeff tells PEOPLE she hopes that "by sharing my images, people can see a genuine, loving and kind nature that was both John and Carolyn." (The couple is pictured here on Martha's Vineyard in 1996.)

"I sincerely hope people can enjoy the photos and see a taste of something unique in all the perfection and imperfection that was their life," Chermayeff says.

 
13of 13

The Way They Were

JFK JR. and Carolyn
SASHA CHERMAYEFF

From left: Carolyn and John on the beach at Martha's Vineyard with Chermayeff's son, Phineas, in 1996.

 
 
 
 
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A Dynamic Duo.

 

CR Fashionbook

CR Fashionbook

BY Diego Villarreal Nov 25, 2019

 

 
 

 

From the moment John F. Kennedy Jr. was born–59 years ago today–(and his now-iconic salute to his father’s funeral at the age of three) to when he tragically passed away in a plane crash in 1999, media scrutiny has focused on the oldest son of President Kennedy and Jackie O. When JFK Jr. secretly wed Carolyn Bessette, a publicist for Calvin Klein who was unaccustomed to media attention at the time, the young couple was suddenly thrown into the spotlight and constantly hounded by the press, who documented their every move. In a paparazzi-esque shoot with models Brooke Buchanan and Benj Lee, lensed by Diego Villarreal, and styled by Daniel Gaines, CR explores one of the most infamous couples of the late 20th century who hailed from one of the last remaining bastions of near-American royalty.

 
 
 
 
 
 
 
 
 

PHOTOGRAPHS DIEGO VILLARREAL
FASHION DANIEL GAINES
MAKEUP LOUISE O’NEILL USING BOBBI BROWN
HAIR SIRSA PONCIANO
MANICURIST RICA ROMAIN
CASTING RICKY MICHIELS

SPECIAL THANKS TRIBECA JOURNAL STUDIO

jfkjr1-1-1521487309-scaled.jpg DIEGO VILLARREAL
jfkjr2-1-1521493110.jpg Diego Villarreal
jfkjr3-1-1521493125-scaled.jpg Diego Villarreal
jfkjr4-1-1521493114.jpg Diego Villarreal
unnamed-1521555172.jpg DIEGO VILLARREAL
jfkjr7-1-1521493126-scaled.jpg Diego Villarreal
jfkjr8-1-1521493111.jpg Diego Villarreal
jfkjr9-1-1521493119.jpg Diego Villarreal
jfkjr10-1-1521493123.jpg
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On 2/1/2023 at 4:29 AM, YouNoMe said:

A Dynamic Duo.

 

CR Fashionbook

CR Fashionbook

BY Diego Villarreal Nov 25, 2019

 

 
 

 

From the moment John F. Kennedy Jr. was born–59 years ago today–(and his now-iconic salute to his father’s funeral at the age of three) to when he tragically passed away in a plane crash in 1999, media scrutiny has focused on the oldest son of President Kennedy and Jackie O. When JFK Jr. secretly wed Carolyn Bessette, a publicist for Calvin Klein who was unaccustomed to media attention at the time, the young couple was suddenly thrown into the spotlight and constantly hounded by the press, who documented their every move. In a paparazzi-esque shoot with models Brooke Buchanan and Benj Lee, lensed by Diego Villarreal, and styled by Daniel Gaines, CR explores one of the most infamous couples of the late 20th century who hailed from one of the last remaining bastions of near-American royalty.

 
 
 
 
 
 
 
 
 

PHOTOGRAPHS DIEGO VILLARREAL
FASHION DANIEL GAINES
MAKEUP LOUISE O’NEILL USING BOBBI BROWN
HAIR SIRSA PONCIANO
MANICURIST RICA ROMAIN
CASTING RICKY MICHIELS

SPECIAL THANKS TRIBECA JOURNAL STUDIO

In some pictures John is not him, is a model. Why lie?????

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