The Wilpon family, a wealthy and well-connected New York clan, should have been everything sports fans would want in the owner of a team. They were local, passionate about their game and desperately wanted to win.

It didn’t work out that way.

The legacy of this New York real estate family’s stewardship of its beloved team, the New York Mets, ended up reflecting many aspects of the family itself. There were periods of success, but also dysfunction, intense rivalries among relatives and a financial crisis that, for a time, threatened much of what the family had built.

At their best, the Wilpons, self-made multimillionaires from the city’s outer boroughs, shined as generous philanthropists who occasionally broke the bank for a star player. At their worst, they were a squabbling, disorganized clan with a baseball team that fans saw as inept and thrifty, and functioning as a vanity play for the family scion, Fred Wilpon, and his eldest son, Jeff, who has overseen a team with mostly disappointing results since 2002.

After Wednesday, when the Wilpons announced they were negotiating to sell controlling interest in the Mets to the hedge fund billionaire Steve Cohen, a minority investor, in a deal that valued the team at more than $2.5 billion, a narrative that had been roiling the family in recent months emerged into public view.

With Fred Wilpon, 83, and his siblings aging, their children were increasingly wary of having Jeff Wilpon, their aggressive, short-tempered relative, in charge of the family’s most valuable heirloom. That issue will go away with a deal to sell Cohen 80 percent of the franchise that will give the family a huge profit, consideringwhat the Wilpons paid each time they increased their stake in the Mets.

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Tensions between Jeff Wilpon and his relatives have been brewing for years. Many of them work with Sterling Equities, the family’s closely held umbrella company, but the baseball team, which last won a World Series in 1986 — before the family took full control — was largely Jeff’s domain.

For years, some family members have questioned his choices behind the scenes.

In 2003, for example, Jeff and his father called on Jeff’s younger brother, Bruce, who is fluent in Japanese, to help pursue the free-agent infielder Kazuo Matsui.

Soon after Matsui joined the Mets in 2004 and reported to spring training, he injured his finger. Jeff Wilpon was adamant that Matsui play in televised spring training games to build excitement for the season after a last-place finish a year earlier. Bruce was more protective of Matsui and urged caution.

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The disagreement came to a head when Jeff, seeing a promotional opportunity, wanted Matsui on the field. Bruce pushed back. The argument grew heated and ugly, as Jeff dug in. After that, Bruce rarely, if ever, was involved with the team again.

Such accounts of the family and its decision to sell are based on interviews with more than a dozen people with direct involvement with the Wilpon family and the Mets, nearly all of whom asked not to be identified so as not to damage their relationship with the family. Through a spokesman, Fred and Jeff Wilpon declined to comment.

From real estate to baseball

Before they ventured into baseball, the Wilpons were a blip on the New York real estate scene. Fred Wilpon still rode the train from his home on Long Island to his office in Manhattan. He and his family owned and managed a collection of properties but as empires went, their portfolio was tiny compared with those of New York’s more renowned families — the Lauders, the Tisches, the Newhouses.

Then, in 1980, Wilpon acquired a 1 percent stake in the Mets when Doubleday, the publishing company, bought the team. Six years later, against the wishes of his partner Nelson Doubleday, he exercised a clause in his contract to wrest control of 50 percent of the team. Practically overnight, Wilpon became a major New York figure. His phone started to ring more often with business proposals. There were invitations to serve on the boards of prestigious charities. And his baseball team began to occupy more of his time and interest.

During the years he controlled the team, Nelson Doubleday had insisted that neither his children nor Wilpon’s have a role within the team. Insiders at the time said it was well known that the purpose of the rule to was exclude Jeff Wilpon, who had played baseball at Palm Beach State College and was even drafted twice by major league organizations.

“Doubleday was very hard on Jeff,” one executive said.

But when Fred Wilpon and his relatives bought the remaining 50 percent of the Mets from Doubleday 2002, for about $135 million, he also cleared the way for Jeff to take a more active role in team affairs. Jeff quickly emerged as a dominant figure. Jeff’s siblings, who attended Brown University, never had much interest in sports. For Jeff, though, running the team was a dream job.

And few would have complained about the Wilpons’ hands-on management style had the team been successful. But since the Wilpons assumed full control of the team nearly two decades ago, the Mets have made the playoffs only three times. They have not won the World Series since 1986, despite the financial advantages of playing in the country’s largest market. During that same period, the Yankees have been to the postseason 14 times and won the 2009 World Series, their fifth championship in 13 years.

Both Jeff and his father, who played high school baseball and basketball with Sandy Koufax, the Hall of Fame pitcher, fashioned themselves as baseball experts. Their involvement in the operations of the team often had few limits.

Fred Wilpon liked to watch pitchers throw their bullpen sessions, and sometimes interacted during the process. “Fred knows just enough to be dangerous,” one former pitching coach said. If a player on the major league roster got injured, Fred and Jeff would weigh in on which minor-league affiliate would host the player’s rehabilitation assignment. Jeff liked to be informed about all roster moves, even those in the low minor leagues.

Fred also liked to talk to his manager in his office before games. He once suggested to Terry Collins, who managed the Mets from 2011 to 2017, and his pitching coach Dan Warthen, that they call pitches from the dugout. Gracious and collegial in public, he sometimes yelled in baseball meetings, and would ask derisively about a struggling player, “Who scouted him?”

In an era when front-office employees in the majors are screened extensively for their skills with math and advanced statistics, Fred Wilpon, a friend of Chris Christie, the former New Jersey governor, once asked that Christie’s son, Andrew, be hired as an intern. Andrew, a former Princeton University baseball player, is now the Mets’ assistant director of amateur and international scouting.

A micromanaged team

In conversation, Jeff Wilpon often drops the names of former baseball greats with whom he speaks and plays golf. He regularly cozied up to star players in the clubhouse, and occasionally spoke to players or coaches about their performance in the tunnel connecting the team’s dugout and the locker room.

There were other puzzling incidents. One star player recalled how Jeff flipped a new baseball glove toward him one day and instructed him to break it in. (The player ignored the command.) And in July, the Mets traded the pitcher Jason Vargas to the Philadelphia Phillies for cash and a light-hitting minor league catcher with little value named Austin Bossart. Bossart, some in the organization noticed, had played baseball with Jeff Wilpon’s son on the University of Pennsylvania baseball team.

Former executives said the team changed philosophies from year to year, and sometimes from month to month.

“We were never given a clear number for the payroll,” one official said. Recalling how Fred Wilpon handled matters, the official said, “In January, he would say, ‘O.K., you’ve got more money to spend.’ Well, we wished we had known that in November when it counts.”

There were occasional successes. One of Jeff’s initial duties was to oversee construction of the Brooklyn Cyclones’ stadium in Coney Island, and then the much larger project to build Citi Field. The stadium is now considered first-rate, but it hit some early bumps. When it opened, Mets fans complained that the stadium celebrated the team Fred Wilpon had worshiped as a child, the Brooklyn Dodgers, more than the Mets. The fences were initially so far from home plate that Mets batters, who played there most often, struggled and free agents cited it as a reason to stay away from the club. Eventually, the Wilpons added a Mets Hall of Fame and moved the fences in.

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In 2014, Jeff Wilpon was accused of gender discrimination by a former director of ticket sales who said he had chided her for being pregnant while single. There were several witnesses to the incidents, and the Mets ultimately agreed to a financial settlement in March 2015 that resolved the complaint.

And yet, even as the Mets and the Wilpons fumbled along, fans tended to embrace the team’s identity as the idiosyncratic but more approachable member of New York’s baseball universe. Then, in December 2008, everything changed.

With the country tumbling through its worst economic crisis since the Great Depression, the world was introduced to Bernard L. Madoff, a New York investor who was revealed to have been running one of the largest Ponzi schemes in American history. Madoff’s investors included dozens of boldfaced names and institutions, many of whom were ruined by his fraud. The investors also included the Wilpon family.

Wilpon and his brother in law, Saul Katz, had over 500 accounts with Madoff, according to one analysis. They were sued for $1 billion by the trustee for the victims who claimed they knew, or should have known, that Madoff’s returns were fraudulent.

The collapse of Madoff’s fund changed everything for Wilpon and Katz, depriving them of an automatic source of income that had helped plug the financial holes of their often struggling baseball team. Hundreds of millions of dollars — even some deferred payments owed to Mets players — had been invested with Madoff and his magical guaranteed 15 percent, or better, return.

As the Madoff scandal unfolded, and the broader Wilpon family empire was forced to pay a multimillion-dollar settlement by the trustee unwinding the fraud, the Wilpons struggled to maintain control of the Mets. The family resorted to taking out at least $65 million in loans just to meet payroll and other obligations, including $25 million from their fellow owners in Major League Baseball. After years of costly litigation, the Wilpons agreed to pay $61 million to the trustee.

Since the Madoff crisis, and as Fred Wilpon and his siblings and relatives approached their 80th birthdays, the decision for the family to relinquish control of the Mets seemed almost inevitable. Since 2011, the Wilpons have been seeking investors to help carry its financial burdens.

When the Wilpons first invested in the Mets, baseball was a mostly harmless dalliance for wealthy businessmen. Now it is an $10 billion-a-year business, with huge risks. People familiar with the team’s finances said the Mets have lost more than $60 million during each of the past two seasons, as the team struggled to attract fans, and they are at the limit of debt allowed by Major League Baseball rules.

In 2012, with the economy rebounding, the Mets sold 12 minority shares in the team, including one to Cohen, raising $240 million. That enabled them to pay back loans that were overdue.

Their two-thirds ownership of Sportsnet New York, the regional sports network, has helped cover financial shortfalls related to the team, which is now carrying hundreds of millions of dollars in debt, exacerbating tension between Jeff Wilpon and his relatives. In recent months, selling the franchise became the most equitable way to divide up the asset among the Wilpon family members.

When the deal with Cohen closes, however, the Wilpon family will be reduced to minority investors in the team. According to the deal, Fred and Jeff Wilpon will maintain what figure to be largely ceremonial roles during a transition period. And then the Wilpon clan will once more be just another New York real-estate family with a closely held company that, like all real-estate families, wins some and loses some.

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