This is the unusual story of the unlikely relationship between the families of Vineyard photographer Peter Simon, his rock ’n’ roll star sister, Carly, and baseball pioneer Jackie Robinson.
The tale begins in 1955, when the fleet-footed Mr. Robinson — the first African-American Major League baseball player in history — was leading the Brooklyn Dodgers to their first World Series title. 
While Mr. Robinson patrolled second base, his wife, Rachel, was combing the Connecticut suburbs for a family home. It was a painful search, derailed by racist brokers and neighbors who were afraid that selling to an African-American family — even to Mr. and Mrs. Jackie Robinson — would cause lower property values, block busting, or worse.
These troubles were chronicled in a local newspaper, attracting the attention of neighboring ministers as well as Andrea Simon, a sharp-eyed, energetic community activist and the wife of publisher Richard Simon.
Concerned citizens called a meeting at the Simon home. Almost immediately, a bond was struck between Rachel Robinson and Andrea Simon; later that afternoon, the pair went house-hunting together.
This was a more fruitful search. On that afternoon, with her new friend Andrea in tow, Mrs. Robinson found the property of her dreams — just a mile down the road from the Simons.
“It was exactly what I had been looking for,” Mrs. Robinson, now 74, told the Gazette recently. “I was just thrilled. The minute I saw it, I knew that I wanted it.”
Thus began the relationship between the Robinsons and the Simons. The Robinsons stayed in the Simon family home while they waited for the completion of their own Stamford house. Andrea and Rachel were now close friends, sharing dinners and the company of their children — Peter, Carly, Joanna and Lucy Simon, and Jackie Jr., Sharon and David Robinson.
The Simons also became dedicated fans of Jackie Robinson Sr., who was already a baseball legend.
“My whole family was crazy about baseball,” Peter Simon recently recalled. “And whenever the Dodgers were on television and Jackie Robinson stepped up to the plate, my mother would lean over and kiss the screen — good luck so he’d get a hit.”
Ten seasons after he broke baseball’s color barrier, Mr. Robinson retired from baseball in 1956. This meant more time with his family in Stamford, plus a serious crash course in baseball for Peter, Carly and Jackie Jr.
“Jackie spent so much time teaching us about baseball,” Peter said. “We’d stand out in the backyard, and he’d hit us grounders with a tennis racquet and a tennis ball. He used to whale the ball and hit these towering high flies. 
“We were so into it, especially Carly, who was a true-blue Dodger fan.”
Peter grew to be close with Jackie Jr., who was his age. For several Stamford summers and sleepaway camps, the two were inseparable, hanging out on lazy, hot days and hitting rocks into the Robinson family’s pond. 
Mrs. Robinson recalls many summer gatherings at the Simon home. Mr. Simon, who co-founded the Simon & Schuster publishing company, was a major figure in Manhattan cultural circles, and his backyard parties were often glorious affairs, with guests such as Benny Goodman and Jimmy Durante.
“It was a very active, fun place to go,” Mrs. Robinson said. “They always had so many interesting guests. There were games and outdoor activities and many families. Andrea loved to feed people. We just liked going there.”
Occasionally, these outdoor parties revolved around high-spirited baseball games. Thanks to Mr. Robinson, there is one particular game that Peter Simon will never forget.
“When I was little, there was this woman named Lucy Monroe who used to sing the Star-Spangled Banner before every Dodgers home game,” he recalls. “I got very attached to her. I used to imitate her all the time and when she would sing on the television, I would tell everyone in the house to be quiet.
“Well, one day, we had a baseball game up at our house, and Jackie brought Lucy Monroe all the way up to Stamford. She sang the Star-Spangled Banner before our little game in the backyard.”
Despite these unexpected, kindly gestures, Peter Simon remembers Jackie Robinson as a low-key person, a man who never sought fame or attention.
“I really don’t think Peter was aware of Jack’s celebrity,” Mrs. Robinson said. “I’m not surprised. Jack was not the kind of person who tried to impress you with that sort of thing. He was very much at home when he was with friends and he was particularly close to children, especially small children. When we lived in Brooklyn, all the neighborhood boys would sit on the front stoop and wait for him to come home from his game.”
As Jackie Jr. and Peter Simon grew older, they developed different interests and took separate paths. Peter became an avid photographer; Jackie Jr. enlisted in Vietnam where, sadly, he grew addicted to drugs. Upon his return, he successfully completed a rehabilitation clinic and became a youth counselor, only be killed in an automobile accident in 1971.
But over these years, Rachel Robinson and Andrea Simon remained close. Richard Simon died in 1960, and Andrea — always an independent-minded, indefatigable soul — began spending more time on Martha’s Vineyard.
“I loved visiting her on the Vineyard,” Mrs. Robinson said. “I loved the natural beauty of the place, and we’d take long walks in the woods and along the beaches.”
Mr. Robinson also visited the Island a few times. Peter Simon recalled one such trip, when Mr. Robinson came to watch him play in a pickup softball game at the Menemsha School.
“He didn’t want to be identified,” Mr. Simon said. “He just sat on the bench and watched the whole game. But the word got out — people were saying, ‘Hey, that’s Jackie Robinson’ — and people wanted him to come up and take a few swings at the plate. He didn’t do it, but you could tell from the glimmer in his eye that he wanted to go up there and get a hit.”
Jackie Robinson died on Oct. 23, 1972, at the age of 53. Subsequently, Mrs. Robinson grew even more close with Andrea Simon; in addition to large families and fame, both women now shared the loss of a husband. It was a bond that lasted until 1994, when Andrea Simon died at age 84.
“Andrea and I had more than a friendship — we were like sisters,” Mrs. Robinson said.
This year marks the 50th anniversary of Jackie Robinson breaking baseball’s color line. There will be ceremonies, presidential tributes and teary recollections, but this is not a total celebration. A half-century later, the second baseman’s struggle is not over. Said Mrs. Robinson: “The residue of racism is still with us.”
But to Mr. Simon, this anniversary is a more personal moment.
“When I was a kid, I didn’t really think very much about the effect Jackie Robinson had on me,” he said. “But now, I think about it all the time. He taught me so much.”