Political Families- The Saga of John F. Kennedy, Jr and Carolyn Bessette- My Perspective
Yes, I grew up with the ultimate Kennedy tragedy glued to the black and white TV set at nine years old. John Jr’s salute is forever a sign of family solidarity.
Sometimes, we have to take various streaming documentaries with a big grain of salt. Even the 6 p.m news- is “newsertainment” at best in 2026.
After reviewing various expert opinions online we know that the “Love Story of John F. Kennedy Jr. and Carolyn Bessette” was fictionalized and romanticized. In particular, the veracity of how the circumstances unfolded prior to the fatal airplane crash.
There have been over 40,000 JFK Sr. books written alone, not including the other cast of characters and interrelated topics.
The American Royal Family has paid an extraordinary price.
The human toll has accumulated beyond all imagination for decades. (Never considering what is fair in life).
True or not, if I was an actual movie reviewer, I would have listed these elements as major themes about John F. Kennedy, Jr, specifically:
1)The horrendous, unrelenting super celebrity burden that was so outrageous, virtually making John and Carolyn prisoners in their own skin and in their loft apartment. This fact alone, set them up for failure in every conceivable way!
2) Immaturity-John’s cocoon upbringing in a multi-generational family set him up to witness all of the resources brought to bear at a moment’s notice; ‘Without having to put in the sweat equity; Where manipulation and power controlled others.
This was the modus operandi. The secret family mantra was protect and cover up at all costs!
This signaled an unrealistic privileged view of life, where every problem was a non-problem, every flaw and frailty was downplayed or lied about and every real tragedy accumulated more scars in their vulnerable psyches and hearts.
The full truth could never be revealed. Their armor against it all was family loyalty. This way of life almost guarantees that children will not develop the needed maturity in which life is neither normal nor predictable or manageable.
3) Extreme Risk Taking - When the clan will run to the rescue and fix everything imaginable and unimaginable by wealth, influence and power, what on earth is there to worry about?
In John’s mind, everything would work out within this scenario. Responsibility, accountability, maturity, communication were concepts that were not understood or practiced.
Hyannis Port, Massachusetts
The big dichotomy, the elephant in the room, always present in the portrayal of John F. Kennedy Jr, was that he was aware that on the surface he could get away with anything given his charm and good looks.
This was really a false sense of confidence that he showed the world. Throughout the documentary, he struggled in his heart of hearts with ‘being a failure.’
It reared its ugly head so many times in his relationship with Carolyn, while trying to measure up for his mother Jackie, pass the New York Bar Exam, keep his magazine George afloat, and while trying to be a proper and thoughtful husband. He verbalized it particularly, when their marriage was in deep trouble.
The documentary made it appear that John did virtually no work, preferring to play all day, leaving his business partner to make it successful. I suspect the truth lies somewhere in between.
The other secret revealed according to the documentary, told during the final scenes, was that although John swore to Carolyn that he would never, ever pursue a career in politics (a condition of her ‘saying ‘yes’), he, in fact, had at least one secret conversation about doing just that.
The depths of desperation concerning his beloved magazine supposedly drove him to it.
Maybe he thought that in his family, this choice was a ‘no brainer.’
Carolyn Bessette- Kennedy-
In the documentary, Carolyn’s allure was her indifference to John Jr’s status and the fact that she had goals, was her own person and never wanted to be a celebrity wife. This fact motivated John like he had never been motivated before.
Carolyn underestimated the enormous task of becoming a Kennedy wife and paid dearly for it, even in the most everlasting way- tragic death.
She showed her vulnerability in waffling back and forth about his proposal ( Who wouldn’t?). She also admitted her high standards and struggle with the fact that her parents were divorced - something she wanted no part of.
The writers drove home the point that Carolyn was like a caged tiger in their apartment, with nothing to do, as the paparazzi ruined their daily quality of life and any chance of her finding a real job, which threw her into a tailspin of disillusionment.
Although they were in marriage counseling, Carolyn learned that love does not always conquer all. But, the tragic irony of this truly human story was that her sister, Lauren Bessette, (her true confidant), convinced her to somewhat compromise her principles and ‘do it for John’.
(i.e. Attend the event for the revitalization of George Magazine and their impromptu trip to fly to Martha’s Vineyard and Hyannis Port in Massachusetts the night they met their fates.
The Plane Crash-Reams have been written and broadcast about the whys and what really happened.
In a literal and emotional sense, it was ‘the perfect storm’ on July 16, 1999. Some of the major contributing factors were:
John was not appropriately certified for night flying or instrument flying;
The sea and sky blended into one, combined with ‘tricking the brain’ causing spatial disorientation;
John was using weather data that was 2/1/2 hours old;
He declined help from at least one instructor;
Delays in John’s, Carolyns’ and Lauren’s schedules contributed to the fatality;
John had only 5 hours sleep the night before after attending a Yankees game with friends and probably was experiencing pain from his broken left ankle;
John was stressed and wanted to prove to his wife that he could be the husband she needed;
John filed no flight plan;
John did not radio for help during the flight.
Period, end of story… How could someone be so reckless with life? We will all wonder about this forever…
***The one good thing to come out of this awful aviation disaster, is that this experience has been analyzed and used to train thousands of pilots concerning what to do and not do. ( Probably NOT the legacy JFK Jr. wanted!)
The Kennedy family could not and would not compromise their lifestyles by ‘living large.” Assassinations, Aviation and Car Accidents, Skiing fatality, Cancer, a failed lobotomy for Rosemary at age 86, Cerebral Vascular Accident. ,( ‘a stroke’), pneumonia and more took so many Kennedys. ( Undoubtedly, all of the ‘affairs of the heart’ contributed as well…
A Final Footnote-
A final footnote to the long line of tragedies occurred when Tatiana Schlossberg, the daughter of Caroline Kennedy and granddaughter of JFK, passed away from leukemia on December 30, 2025.
This was one day after her 35th birthday and just months before the early 2026 release of the TV series Love Story, which dramatized the 1999 death of John F. Kennedy Jr ; Carolyn Bessette Kennedy and Lauren Bessette
Tragedy begets tragedy….. Many of us have known this life. The resilient keep going…in spite of it all!
Thank you for reading, sharing and commenting!
Donna
Other blogs you should read-
https://donnagore.com/blog/guns-roses-amp-funerals-dont-mix-updated;
https://donnagore.com/blog/the-intersection-of-life-and-death-the-life-of-melissa-milan-revisited