At around the same time, another event took place that turned out to be nearly as important. It happened in the cafeteria at Roslyn High. “It was my junior year, and I was talking with a friend about how we were going to be in Palm Beach over Thanksgiving break, and we were saying we were going to rent a boat to go fishing,” Jeff Wilpon said. “And this little kid came up to us, and he said he was going to be in Palm Beach, too, and he had a boat, and we could go fishing together. He was a freshman, so we basically ignored him. We told him sure, sure, but we never thought anything was going to happen.
“But, when we got down to Palm Beach, all of a sudden a light bulb went off,” Jeff continued. “Maybe we wouldn’t have to pay to rent a boat. Maybe we should call this kid up. Next thing you know, we’re hanging out with this freshman down there. We became friends. It was a weird, freak thing.” The freshman was Mark Madoff.
“Jeff and my sons all went to Roslyn High School together,” Bernard Madoff wrote to me in an e-mail from federal prison in North Carolina, where he is serving a sentence of a hundred and fifty years. “Although Jeff was a couple of years older, they all had many of the same friends and grew up together. Jeff was always a lovely boy and well liked. He was quite an athlete. I first met Fred in the 80’s thru our sons. We both were very family oriented and had many similar interests.”
According to Fred Wilpon, “Jeff was in school and was friendly with Mark Madoff and Andy Madoff—mostly with Mark, because Mark was more his age. Andy was a little younger. And Jeff introduced me to Bernie.” Although Fred Wilpon and Bernie Madoff came out of the same world—during the nineteen-forties, Madoff’s father started a business called Dodger Sporting Goods Corporation—for a few years they had contact only through their sons. Then Madoff made a casual offer to manage some of Wilpon’s money. After Madoff made the invitation a second time, Wilpon happened to have lunch with an old friend named Howard Squadron. Squadron, who died in 2001, was a prominent New York lawyer and was also president of the American Jewish Congress.
“I was having lunch with Howard one day at the Century Club, where he belonged, and he said something to me about Bernie Madoff,” Wilpon said. “He and his partners were investing now for years and they were doing great. ‘And Bernie is an amazing investor. And he’s got a strategy that is a very safe strategy.’ And I said, ‘Describe the strategy to me. I don’t know too much about that kind of stuff.’ Howard certainly wasn’t looking for major, major returns. He was looking for safety. So he said, ‘You ought to consider investing with him.’ ” Wilpon made his first investment with Madoff in 1985. “So we decided to jump in,” he said. “And we jumped in very small. And, as the years went, it became more and more and more and more.”