Elsa Garrison / AP

By just about any measure of an athlete’s “success,” Derek Jeter grades out as exceptional. Statistics? He tallied 3,465 hits, sixth all-time. Championships? He won five of them with the Yankees. Money? He earned more than $250 million in salary throughout his career. Crossover stardom? He was baseball’s most famous player and remains a staple of tabloid gossip. Adoration? Yankees fans name their children after him, while even rival supporters grant grudging re2pect. By the time he retired from playing in 2014, his resume was essentially flawless.

And that’s why Jeter’s brief tenure as CEO of the Marlins has been so jarring. In the five months since Jeter and the retired businessman Bruce Sherman agreed to buy Miami’s baseball team for $1.2 billion, they have traded their two best players, angered an already jaded fan base, fired beloved team employees, and committed a stream of public-relations faux pas. After surviving 20 years under the New York spotlight with nary a major controversy, the 43-year-old Jeter has occupied a new role this offseason: baseball villain.

Last week, the Miami Herald rolled out a multi-part series detailing a confidential document Jeter reportedly circulated to investors last summer as he assembled an ownership group. Per the Herald, Jeter vowed to slash payroll in hopes of generating profit, while somehow increasing attendance at the same time. The latter promise, which fell somewhere between optimistic and delusional, was clearly composed by a man accustomed to success. Its public airing, however, calls attention yet again to Jeter’s repeated missteps.

Jeter’s involvement with the Marlins was messy even before it officially began. His initial partnership with former Florida Governor Jeb Bush fell apart last spring when, according to Bloomberg, the former shortstop demanded complete control over the team’s business and baseball operations. Undeterred, Jeter partnered with Sherman, and together the duo pushed toward a purchase.

But before the sale was finalized, Jeter found himself waist-deep in controversy. In September, the Herald reported that the Marlins’ prospective new owners planned to cut payroll from $115 million (21st highest in baseball) to as low as $55 million, a figure that would likely make them the cheapest team in baseball.The news stung bitterly for fans who had hoped Jeter and Sherman might offer a contrast to previous penny-pinching regimes and for taxpayers who had forked over $488 million in bonds to build the stadium that ownership stood to profit from. And then things got worse.

Later that month, the Marlins informed four high-profile and beloved employees —the Hall of Famers Tony Pérez and Andre Dawson, the World Series–winning manager Jack McKeon, and Jeff Conine, a former player nicknamed Mr. Marlin—that they would not have jobs under the new ownership. Instead of firing the franchise icons himself, Jeter reportedly delegated that awkward responsibility to the outgoing president David Samson. Then, after a public backlash, the neophyte CEO attempted to bring back Conine, Perez, and Dawson in diminished roles with reduced pay. All three declined. In what would quickly become a trend, Jeter had made a questionable decision and executed it clumsily.

MLB owners approved the Jeter-Sherman ownership group on September 27, and the sale became official days later. Almost immediately, Jeter began shopping Giancarlo Stanton, the reigning National League MVP and arguably the greatest player in franchise history. From a baseball perspective, trading Stanton was a defensible move. For a Marlins team that had floated aimlessly through baseball purgatory—not good enough to contend for the playoffs but not bad enough to embark on a rebuild without angering fans—trading Stanton for a package of top young players would at least mean committing to one course of action.

The problem was, the Marlins appeared interested less in restocking their farm system and more in scrubbing Stanton’s large (but deserved) contract from the franchise’s balance sheet. So when Stanton used his no-trade clause to block several potential trade destinations, Jeter and company, according to reporting from the Herald, threatened Stanton that if they couldn’t trade him, they’d deal away his most talented teammates, leaving him to waste away on a last-place team.

The Marlins wound up trading Stanton to Jeter’s former team, the Yankees, unloading most of the slugger’s contract but reaping only a modest haul of prospects. (Days later, they sent another All-Star, the outfielder Marcell Ozuna, to St. Louis for a similarly meager return.) As fans stewed, reporters prepared to grill Jeter at the Winter Meetings, baseball’s annual convention. Except Jeter never showed up. While his colleagues in other front offices haggled with free agents in Orlando, Jeter was back in Miami, watching Monday Night Football from a suite.  (His absence from the Winter Meetings was partially explained by his presence at an event benefiting hurricane victims.) A week later, he caught an earful from fans, including the legendary Marlins Man, at a turbulent town hall–style meeting, where one team supporter reportedly cried while asking Jeter why he hadn’t pursued any free-agent pitchers.

Most of Jeter’s decisions over his opening months painted him as a baseball executive in over his head, but at least one choice suggested something even less palatable. In December, Yahoo revealed the Marlins had fired a longtime scout who was hospitalized following colon surgery and was waiting on a kidney transplant. The story, complete with tragic quotes from the deposed employee, made Jeter sound heartless. The Marlins’ choice to publicly blame the president of baseball operations Michael Hill for the fiasco made the former Yankees captain look unaccountable as well. Once again, the Jeter-led franchise had created a problem for itself and made the situation worse at every turn.

Of course, it’s unfair to pin the Marlins’ blunders on Jeter alone. Sherman, as the Marlins’ moneyman, presumably made the final call to slash payroll, and Hill may bear some responsibility for firing the hospitalized scout and mishandling the Stanton trade. But Jeter chose to be the public face of this ownership group, and he accepted a contract that apparently awards him bonuses not for winning teams, but for profitable ones. Jeter may not deserve full blame for the Marlins’ complications, but as CEO he has earned a share of it.

And although sports history is dotted with great players who floundered as executives (Michael Jordan, Wayne Gretzky, Isiah Thomas, and more), Jeter stands out. Few athletes have entered a front-office role with as spotless a reputation, and fewer athletes have compromised that reputation so quickly. Because not only have Jeter’s personnel moves fallen flat, but his actions have also chipped away at his previously unblemished image, as many fans question not only his competency, but also his intentions.

This version of Jeter didn’t materialize from nowhere, and it’s tough not to glance back at the former shortstop’s playing days in search of clues. Did he fall on his sword for a teammate often enough as Yankees captain? Did his beefy endorsement portfolio hint at a lust for profit? Maybe some coldness always lurked beneath his famously inscrutable disposition. Or, on the other hand, maybe this string of crises constitutes a mere blip. Jeter’s tenure in Miami is only months old, and if he avoids further scandal and leads the flailing Marlins back to the playoffs, his rocky opening months could fade away quickly—much like the 56 errors in a season he once committed as a 19-year-old in A-ball.

Regardless of how Jeter’s front-office career plays out, his on-field legacy remains safe. Fans in New York and beyond will forever admire his talent, grace, and clutch performance. In the summer of 2020, he will assuredly stand at a lectern in Cooperstown, New York, to accept his well-earned Baseball Hall of Fame plaque, and no number of objectionable firings or controversial contract clauses will jeopardize that. But Jeter’s mishaps have eroded his status as baseball’s unimpeachable ambassador, offering a less flattering set of characteristics one might know him by. As a player, Jeter enjoyed one of the most successful careers in sports history. As an executive, his reputation hinges on how well he learns to fail.

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