Two Friends From Two Wainscotts

A tale of connections and coincidences
John McCaffrey and Scott Kennedy met up in New York City this month to discuss their recent projects. Jennifer Landes

Thanksgiving is a time for families and old friends. The story of the friendship of Scott Hamilton Kennedy and John McCaffrey touches on both. It is also a tale of connections and coincidences, all born of two Wainscott households, one on each side of a subdivision line that separates the Georgica Association from the rest of the hamlet.

Mr. McCaffrey’s grandparents were Irish immigrants who came to Wainscott to work in the sprawling houses of the association. His grandmother Mary Lynch worked at Kilkare, probably the most photographed house in the Hamptons, overlooking Georgica Pond and the Atlantic. Mr. Kennedy’s  father, Michael Kennedy, who died in January, was a prominent criminal lawyer also known for representing Ivana Trump in her divorce from Donald Trump. He bought Kilkare as a summer residence in 1976.

Mr. McCaffrey’s grandmother was originally a linen maid to the Edwards family, the house’s first occupants. “It’s an old, old house,” he said, dating from 1877. His grandparents met at a weekly beach picnic held on Sundays by the Irish immigrants who worked at the estates. She later joined his grandfather, also named John, at a house owned by the Hendrick family, where he was the groundskeeper, and became a cook. Mr. McCaffrey said the Hendricks gave his family the house on Sayre’s Path where his father was born.

Scott Hamilton Kennedy and John McCaffrey, now in their early 50s, met when Mr. McCaffrey was invited to play in the games organized for the association’s children, “things like softball and flashlight tag,” he said. The two boys often played together on the third floor of Kilkare, where his grandmother had her room. “It was such an American story that I would visit the same room with Scott, where a maid would bring us lemonade. I thought, ‘Oh god, that was my poor grandmother.’ ” 

The old friends sat down together at a Midtown Manhattan hotel on Nov. 12, the day “Food Evolution,” a film made by Mr. Kennedy, was premiering at the DOC NYC film festival. Mr. Kennedy, who grew up in Berkeley, Calif., and now lives in Los Angeles, was in town to promote the film. They recalled that their friendship really cemented over basketball games at the Wainscott School on a court no longer there. They still play. “Every time he comes in the city I organize basketball games. It’s one way we stay in touch,” Mr. McCaffrey said. 

Mr. McCaffrey, a writer, lives in Hoboken, N.J. The author of two books and several plays, he also teaches creative writing. Mr. Kennedy has been in film production for many years, and Mr. McCaffrey wanted to discuss another of his friend’s projects called Time Capsule Films, inspired by the film producer’s fascination with The New York Times’s obituaries and the recent loss of his father.

“I met a lot of those people The Times wrote about with my father. Some of them may have had media produced on them already,” he said, on series such as PBS’s “American Masters,” but many have not. “Why aren’t we documenting those lives, or the lives of all of us?”

He decided to make those films himself. An Oscar-nominated director of “The Garden,” a feature documentary, he wanted to “take my art and democratize it, scale it down and bring it to more people at a price point for people of certain means. Everybody has a story to tell.”

His first subject was Michael Donaldson, a successful entertainment lawyer, on the occasion of his 75th birthday. Mr. Donaldson, who came out as gay at the age of 60, is shown taking trapeze lessons on the eve of his birthday. “It was a test run to give us a sense of what we can capture in a couple of days of shooting, working with a family and the media they want to include.” 

“Food Evolution,” his other current project, is likely to be more controversial. The film, narrated by Neil deGrasse Tyson, looks at how science is distrusted not just on the right in religiously conservative circles, but also on the left, where fears about vaccinations and genetically modified organisms have persisted in spite of scientific evidence that shows they are safe. 

Mr. Kennedy said the field of food, science, and sustainability is broad enough that the film could be the first in a series. “I wanted to make a film about science communication and fact-based evidence.” Mr. Tyson strongly agreed with him that “this [genetically modified organism] situation had gotten out of hand.”

Mr. McCaffrey said the Time Capsule concept appealed to him in thinking about the life of his own father, who is 84. “He is one of the last of the generation that has this institutional memory of that earlier time” in Wainscott, he said, citing rumrunning during Prohibition and the Irish and Italian workers on the South Fork who helped bring in the hooch from the boats moored off the coast. 

He would love to have his father’s stories preserved, he said, but for now, he is using some of the period’s history as the inspiration for a novel. 

His father sees the South Fork’s traffic and crowds as a sign of progress, he said, but the son is “sad about the land being gobbled up and sad about the environment. My dad could catch tuna off the beach. Now you have to go 600 miles out.”

Mr. Kennedy agreed. “So many people who go out there have no appreciation of how beautiful it is. They go to the beach and parties or are there to show off that they are wealthy enough to be there.” He added, however, that “most of the wealthy people I know out there love it and treat it with respect.”

This article was altered from the print version to correct a misunderstanding regarding the status of Kilkare. The house, which was referred to in the print version as being sold is actually still owned by Eleanora Kennedy, who is Scott Hamilton Kennedy's stepmother.