“We’re snakebitten, baby,” Wilpon said. Clockwise from left: David Wright, Wilpon, Jason Bay, Terry Collins, and Jose Reyes. Photograph by Steve Pyke

This article can be found in “At the Ballpark,” a collection of New Yorker baseball stories for the iPad.

Nearly a decade ago, Fred Wilpon, the chairman and chief executive of the New York Mets, had his first meeting with the architects of what would become Citi Field, the team’s new ballpark, in Queens. “The first day the architects came to the site, they started saying blah, blah, blah, and I said to them, ‘Let me tell you how this is going to work,’ ” Wilpon told me recently. “ ‘The front of the building is going to look like Ebbets Field. And it’s going to have a rotunda—just like at Ebbets.’ And then I said, ‘Guess what. Here are the plans for Ebbets Field.’ And I handed them over.”

As we spoke, Wilpon was walking through the rotunda of the new stadium, which opened in 2009. The façade does indeed resemble that of Ebbets Field, the home of the late Brooklyn Dodgers. The rotunda serves as a memorial to the life and work of Jackie Robinson, who broke baseball’s color barrier when, in 1947, he joined the Dodgers, and who, for his achievements on and off the field, remains Wilpon’s hero. Photographs of Robinson line the rotunda walls, and in the middle of the vast room an aluminum sculpture of his number, 42, rendered in Dodger blue, stands as a kind of shrine.

When Citi Field opened, the Brooklyn focus drew some criticism. After all, the Dodgers left Brooklyn in 1957, and Ebbets Field was demolished shortly thereafter. Only the very oldest fans have any first-hand memory of the place. The Mets, who had been in existence for almost a half century, were virtually ignored in their own home. “All the Dodger stuff—that was an error of judgment on my part,” Wilpon told me. Still, the ballpark combined the guiding preoccupations of Wilpon’s professional life—baseball and real estate. More than that, the stadium, in its architectural homage to Ebbets Field, underlined the omnipresence of Brooklyn, where Wilpon grew up, in everything that followed.

Wilpon, who is seventy-four, has run the Mets since 1980—for more than half his adult life. He has the rolling, slightly pained gait of an ex-athlete, a well-trimmed crown of silver hair, and a taste for fine tailoring, even in casual clothes. He walks the corridors of Citi Field with such a proprietary air that it’s not necessary to make out the bodyguard, hovering at a discreet distance, to recognize that he is the boss. Wilpon has a deft touch with fans. “I bet my husband that you were the guy who owns the Mets,” a breathless woman said to him. “You win,” Wilpon replied.

In the past two years, the Dodger problem at Citi Field has largely been addressed. The team added a Mets Hall of Fame, just off the rotunda, and plenty of banners and photographs of the Mets’ storied and eccentric existence are now spread around the ballpark. The Mets are a family business, run by Wilpon, his brother-in-law Saul Katz, the president of the team, and his son Jeff Wilpon, the chief operating officer. Jeff supervised the construction of Citi Field on a day-to-day basis, but Fred has an almost tactile sense of every inch. “See the floor here?” he said, as we walked in the corridor outside the Mets’ locker room. “The concrete we put in was too slippery for the guys when they got out of the showers.” So a new, pebbly surface was added, in the Mets’ colors of orange and blue.

Wilpon was making a circuit to visit players and coaches before a mid-April night game. The Mets were off to an awful start. A loss the previous evening had given the team the worst record in the National League. (“THAT STINK? IT’S THE METS,” read the headline in the Post.) Wilpon stopped at the coaches’ locker room and chatted with Mookie Wilson, the first-base coach and long a favorite of both Wilpon and the fans. Mookie (who has almost never been known by anything but his first name) came up with the team in the early eighties and played in the Mets’ last World Series victory, in 1986. (“You want to talk about old?” Wilpon said later. “When Mookie came up, he always had this little kid running around his ankles in the locker room.” That was Mookie’s kid Preston, who went on to play for a decade in the major leagues. “Now that little kid is retired!” Wilpon said, with a laugh.) Wilpon inquired after the health of Mookie’s wife, who has been ailing, then commiserated about the team’s troubles. “We didn’t see these problems in spring training,” Wilpon said. He chuckled with Dan Warthen, the pitching coach, about a member of the staff who tends to dawdle on the mound. “Tell him to throw the fucking ball!” Wilpon said. As we walked on, toward the training room, he said to me, “Those guys are proud. They are teachers. It drives them crazy to lose.”

Three pitchers, including Jason Isringhausen, at thirty-eight the senior member of the staff, were perched on training tables, their arms iced and swaddled in yards of Ace bandages. Wilpon asked how they were doing.

Fine, they said, almost in unison.

“What are you doing in here if you’re fine?” Wilpon said.

They all laughed.

“C’mon, guys,” Wilpon said, more seriously. “One game at a time, one game at a time.”

He repeated the message when he stopped in to see Terry Collins, the manager, and Sandy Alderson, the general manager, who are both new this year, their predecessors having been dismissed after several seasons of dismal results. Wilpon stepped through the tunnel and onto the field, where the Houston Astros were finishing batting practice. He came upon Pedro Beato, a boyish six-foot-four-inch rookie pitcher with a broad smile displaying a mouthful of braces. Beato, who is twenty-four, was born in the Dominican Republic but went to high school in Brooklyn. Wilpon had shaken hands with the other players, but he gave Beato a hug.

“Brooklyn boy!” Wilpon said. “My man!”

It isn’t a Brooklyn boy but, rather, a son of Queens who now threatens to undo Fred Wilpon’s life’s work: Bernard Madoff. Wilpon and Madoff had much in common. Wilpon is just a year and a half older than Madoff, and both grew up as outer-borough strivers. Three decades ago, when they met, the two men were already rich and respected beyond their youthful dreams; both were poised to become leaders in their fields. Sterling Equities, Wilpon’s company, became a national power in real-estate development, and also acquired interests in biotech, cable television, and, of course, baseball. Bernard L. Madoff Investment Securities, L.L.C., developed a pioneering electronic stock-trading operation, and Madoff himself operated a separate money-management business, which he made available to a select group of investors. Fred and his wife, Judy, and Bernie and Ruth Madoff became friends, if not intimates, sharing occasional trips and dinners a few times a year. Both families had vacation houses in Palm Beach, and they enjoyed a landmark night at the movies there. “It was the first time I ever got in as a senior citizen,” Wilpon recalled. “We were going to meet them at the movie theatre in West Palm. And I remember going to the booth to buy the tickets. And Bernie was of senior-citizen age at that time, too, but I didn’t think Ruth was. So I bought three senior citizens and one regular, and we laughed about it.”

Mostly, though, the relationship was about business. Starting in the mid-eighties, Wilpon, along with his partners, his family, and his friends, began sending money to Madoff to manage. The returns were not spectacular, but they were steady; indeed, that was the core of Madoff’s appeal. In bull and bear markets, Madoff returned about ten per cent a year to Wilpon. He and his partners used Madoff as a bank, sending spare cash Madoff’s way until it was needed for investments or to make a payroll. Sterling employed an accountant whose responsibilities included managing the many accounts that the firm and its partners and associates had with Madoff. The investments took place automatically, without any specific orders from the Sterling partners.

The Wilpon stake with Madoff grew to be enormous. There were eventually some four hundred and eighty Sterling-related accounts with the firm: three hundred or so belonged to Wilpon, his partners in Sterling, and their family members, trusts, and charities; the other accounts were owned by close friends, employees, and business associates. In all, the Sterling cluster was one of the largest groups of Madoff investors. On December 11, 2008, the day that Madoff’s money-management business was revealed to be the largest Ponzi scheme in American history, Wilpon and his partners’ stake was listed at five hundred and fifty million dollars. On that one day, it all vanished.

That was bad enough. Then, last December, Irving Picard, a lawyer at the firm of Baker & Hostetler, who is the bankruptcy trustee charged with salvaging assets to compensate Madoff’s victims, filed a lawsuit against Wilpon and his partners. “There were thousands of victims of Madoff’s massive Ponzi scheme,” Picard wrote. “But Saul Katz is not one of them. Neither is Fred Wilpon.” Instead, according to Picard, Wilpon and Katz were enablers, virtually Madoff’s accomplices in the vast crime, who “willfully turned a blind eye to every objective indicia of fraud before them.” For the Madoff investors, Picard had adopted a formula whereby the “net winners”—that is, those who cashed out more than they put into their Madoff accounts—would pay back their winnings to compensate those who were net losers. By this standard, the Wilpon people would have had to repay approximately a hundred and sixty million dollars in profits that they had taken out of their Madoff accounts over the years. (The precise amount is in dispute.) However, Picard was treating Wilpon the way he treated those he believed to be complicit in Madoff’s fraud. From this group, Picard was seeking a refund of their Madoff principal, not just their profits. In other words, they would have to make good even on the money they had lost in the scam. Specifically, he was demanding that the Wilpon group pay damages of approximately a billion dollars.

Fred Wilpon is rich, but he is not Michael Bloomberg. He cannot simply write a check of that size to make the case go away. The mere filing of Picard’s lawsuit forced Wilpon into a painful financial reckoning. Most important, the lawsuit compelled him to put a big piece of his beloved Mets up for sale. For decades, Wilpon has lived in the fraught and contentious worlds of New York real estate and professional sports and has had an enviable reputation: thoughtful, decent, philanthropic, even kind. But now, in the later innings of his life, he must rise to an unseemly challenge: to salvage his reputation and his fortune, Wilpon must prove that he was a dupe rather than a crook.

The headquarters of the Wilpon empire resembles an English manor house transplanted to a high floor in Rockefeller Center. Wood panelling, thick carpets, and pastoral landscapes in heavy frames offer a serene contrast to the hubbub below. Soft drinks are decanted into crystal glasses. (No Coke; Pepsi is a Mets sponsor.) True, the muted television in the reception area is set to SNY—the Wilpons’ successful cable sports channel—and there is the obligatory LeRoy Neiman painting. But the Neiman shows the trading floor of the New York Stock Exchange, rather than his customary jock kitsch, and the over-all feel of the offices is boardroom, not locker room. The suite previously served as the aerie of the late Steve Ross, when he was chairman of Time Warner. “I liked Steve,” Wilpon told me. “He got his start in the funeral business, so we had that in common.”

Unlike many rich men, Wilpon is an asker of questions as much as a dispenser of opinions. He learns about people’s backgrounds—their home towns, schools, parents, kids—and makes connections from his own wide-ranging life and contacts. It’s a winning trait, especially useful for a salesman. As for the Ross connection, it was actually Wilpon’s father, Nat, who made his living among the deceased—as a manager of Sherman’s Memorial Chapel, which is still welcoming customers on Coney Island Avenue.

Every spring, Wilpon takes a half-dozen or so close friends to Florida, to the Mets’ training camp, at Port St. Lucie, for a long weekend of baseball and Italian food. The men, who call themselves the old farts’ club, have found success in varying fields—Jim McCann founded 1-800-Flowers; Robert McGuire is a former New York City police commissioner—but the similarities among them are striking. All are self-made, grew up in the outer boroughs of New York City, and can now look back on middle age. (Ray Lamontagne, the chairman of the board of City Center, comes from New Hampshire, but otherwise fits the profile.) During one recent lunch together, the old farts had a contest of sorts to determine who grew up in the most modest circumstances. They had all shared a bedroom with siblings, but Wilpon was deemed the winner, because he was the only one who had to share with his sister.

The Wilpons lived in Bensonhurst, and Fred grew up on the baseball fields at the Parade Grounds and in Dyker Park. He pitched for Lafayette High School and for sandlot teams, and quickly drew notice as a professional prospect. Wilpon was so well regarded that he was invited to pitch batting practice to the major leaguers. When he threw at Ebbets, he would get an extra ticket to the games, and he often brought along a friend from high school, Sandy Koufax. “Sandy was one of the best basketball players in Brooklyn,” Wilpon said. “The only reason he joined the baseball team was so we could hang around together. Sandy played first base.”

“I really didn’t play much baseball at all,” Koufax told me. “I didn’t go out for the baseball team until my senior year, when basketball was over and I didn’t have anything better to do. Fred was the baseball player.” Koufax won a basketball scholarship to the University of Cincinnati. There he took up baseball more seriously and stopped playing the infield.

The Dodgers tried to sign Wilpon in high school, but his parents insisted that he go to college. The University of Michigan had a good team, and offered Wilpon a partial scholarship, which he accepted. Before his sophomore year, though, he blew out his arm and was unable to pitch again. Ray Fisher, the baseball coach, made sure that the school converted Wilpon’s athletic scholarship into an academic grant, and he was able to graduate on time, in 1958. Wilpon and Judy, whom he met in Ann Arbor, are loyal alums. In 2008, they supplied most of the funds for a nine-million-dollar renovation of the Michigan baseball stadium, which is named after Fisher. The Wilpons also underwrite dozens of scholarships every year. Fred’s ringtone is the Michigan fight song.

After graduating, Fred tried to sell primitive calculators door to door in midtown Manhattan, and Judy worked as a secretary. One day, Fred decided to try to find Judy a new job. He stopped in at 680 Fifth Avenue, where Branch Rickey, the former president of the Brooklyn Dodgers, was attempting to bring a new team to the city. “When I introduced myself to the secretary, I heard Rickey’s big, booming voice in the background saying, ‘I remember him—send him in!’ ” Wilpon recalled. A half-century earlier, Rickey had graduated from Michigan’s law school and had also coached its baseball team; he said he would be happy to have Judy come by for an interview. Rickey hired her as a secretary for his new operation, which was a predecessor of the Metropolitan Baseball Club. Later, the name was shortened to the Mets. (Judy left the job after a few years to raise two sons and a daughter, but she never gave up her love of baseball. “We’ll be together at dinner in Sun Valley or somewhere, and you’ll look over at Judy and you think she’s zoned out—she’s staring at her lap,” Jim McCann said. “But she is monitoring every pitch in the Mets game on her phone.”)