The Tampa Bay Devil Rays joined the American League as an expansion team in 1998 and immediately became an object of ridicule. Playing in a dingy, depressing stadium in six-color uniforms that could have been pajamas, they finished in last place every season but one for a decade — and next-to-last in the other one. By 2008, though, a former options trader named Stuart Sternberg owned the franchise and had hired a cohort of baseball novices to run it. Sternberg tweaked the colors and shortened the nickname to the Rays. And to the surprise of just about everyone, when his Rays arrived at Yankee Stadium for a doubleheader that September, they led their division.

Mike Mussina, a right-handed pitcher who was in the final weeks of a Hall of Fame career, started the first game for the Yankees. Nearly all right-handers are more effective against right-handed hitters, so teams usually prefer to send lefties up to bat against them. But Mussina, who would win 20 games that season, was an anomaly: Righties hit significantly better against him than lefties did. “Everyone knew it about Mussina — they had the numbers — but nobody had the nerve to do anything different,” Sternberg told me. “We said: ‘Look, this is stupid. We shouldn’t be putting lefties up against this guy. He’s carving them up.’”

The lineup that the Rays’ manager, Joe Maddon, sent out to face Mussina included only one left-hander and two switch-hitters. Maddon asked the switch-hitters to bat right-handed. “I haven’t hit right-handed against a righty since I was a kid,” one of them, Ben Zobrist, remembers thinking. “But my manager thinks it will work, so let’s go with it.”

When Zobrist, an infielder and outfielder who started in the minors with the Houston Astros, arrived at Tampa Bay, he found a low-budget team willing to consider almost anything that might create a competitive edge. It was as if the Rays had taken Billy Beane’s “moneyball” — a concept introduced to baseball fans through Michael Lewis’s 2003 book of that name — and stretched it as far as it would go. “They were looking for different ways to be better so they could compete against the Yankees and the Red Sox,” Zobrist says. “That was the approach of the whole organization. ‘So what if our names aren’t as big as the Yankee names? Why can’t we figure out something that hasn’t been figured out yet?’” In the fifth inning of that game, Zobrist doubled. Then he scored on a single to put the Rays ahead, 5-0. They won that game, and eventually the division. A month later they advanced to their first World Series.

A remarkable run followed. Since April 2008, only two teams, the Yankees and the Dodgers, have won more games. At one point, this poorly supported, low-revenue franchise managed to win 860 games over the course of a decade — that is, it averaged 86 wins a season while playing in the same division as the Yankees, Red Sox and Blue Jays. “What they do down there, I think, is very special,” says Rocco Baldelli, the Minnesota Twins’ manager, who played and coached for the Rays. “Not just in baseball, but in the world of sports and even business.”

Along the way, their iconoclastic thinking spread throughout the sport. Many of their tactics were adopted as industry standards. Some, like repositioning fielders across the diamond — the “shift” — or using relievers to retire a single batter, were so effective that Major League Baseball banned them. “They would play four outfielders at times,” says Mark Attanasio, the owner of the Milwaukee Brewers. “Other times they would play two outfielders. I would say that Billy Beane invented moneyball, and then Stu and his group perfected it.”

It’s quite a success story. Except it also isn’t. Somehow, all that winning never inspired more people to drive to St. Petersburg to see the Rays. “It’s a singular situation in baseball for certain, and all of sports, probably,” Sternberg says, “that a team has won as much as we have but has been at or near the bottom in attendance.” In that sense, at least, Sternberg’s Rays have failed. They’re the only major-league team this century that hasn’t drawn two million fans in a single season.

More than most teams, the Rays are willing to trade emerging stars for low-salaried prospects rather than re-sign them at the going rate. Rob Manfred, the league commissioner, believes that this approach is part of the problem. “Every baseball team,” he told me, “no matter how successful, has to balance the desire to win on the field with the business side of the business, which largely turns on building fan loyalty. A strategy where you have high player turnover, regardless of the success you have on the field, makes it harder to develop a large, loyal fan base. Fans get attached to players.”

When I relayed Manfred’s opinion to Sternberg, he didn’t disagree. “We just don’t think we have the luxury of doing both — winning and keeping those guys,” he said. He shrugged. “So we just win.”

Since taking control in 2005, Sternberg has been trying to increase revenue by building a more enticing home for the team. Last summer, a deal was announced for a glass-walled, $1.3 billion ballpark, to be financed by the Rays, the city of St. Petersburg and the county. Sternberg agreed to cover cost overruns. And then, in October, Hurricane Milton tore the roof off Tropicana Field. In the aftermath, the City Council postponed the final vote on replacing it, effectively making Milton the storm that destroyed two stadiums.

By March, when St. Petersburg was prepared to consider the issue again, the Rays’ projected costs had increased by at least $100 million. When elected officials refused to share the additional burden, Sternberg abandoned the deal. At that point, the city announced it would not negotiate further. This season, while Tropicana Field is being repaired, the Rays are playing in a spring-training park they rent from the Yankees.

Sternberg, now 65, once envisioned passing the team on to one or more of his children. But faced with growing pressure to secure the Rays’ future, he decided to consider a sale. In June, he revealed that he was negotiating with a group led by Patrick Zalupski, a Jacksonville developer.

Sternberg keeps a low profile. Few fans outside his market could identify him, though he will leave behind a legacy that extends far beyond an impressive winning percentage. “They changed the way that many of us think about the game,” Baldelli says of the Rays. His team is also worth more than eight times the $200 million he paid for it. Still, his Rays have never won a World Series, they draw fewer fans than any consistently good team since the days of black-and-white television and he never was able to get them out of the unappealing stadium he inherited. Because of that, he is now reluctantly selling them. And many of the strategies he pursued that made possible all the Rays have accomplished, it seems, are the same ones that will lead to his departure.

Sternberg’s parents owned a business on Brooklyn’s Flatbush Avenue that made decorative pillows from needlepoint canvases. The first time he attended a baseball game, he saw Sandy Koufax pitch at Shea Stadium, an experience that jump-started a lifelong infatuation with the sport. In 2000, when he was 41, Goldman Sachs paid $6.5 billion for the Wall Street firm Spear, Leeds and Kellogg, where Sternberg was a partner. He agreed to stay at Goldman for two years. A young associate named Matt Silverman, who was also a baseball fan, was assigned to work with him. Eventually, Sternberg told Silverman that he planned to invest in a team, and he wanted Silverman to help.

From the beginning, M.L.B.’s Tampa franchise was star-crossed. Tropicana Field, poorly designed and shoddily constructed, was situated on the other side of Tampa Bay from most of the area’s residents. The club’s owner, Vince Naimoli, operated it on a shoestring. The team was terrible, and once the excitement of its first season faded, almost nobody came to see it. By 2002, Naimoli had been trying to sell it for a while. To Sternberg, this seemed an ideal situation. “If we’d bought, I don’t know, the Cardinals, we’d be getting something that’s already working, and you just turn the key, add your little stuff to it,” he says. “This was more fun.” He and a few partners started the process of buying it that winter, though Sternberg didn’t take full control of the franchise until October 2005.

At the time of Sternberg’s initial investment, Bud Selig, then the league commissioner, suggested he relocate to the area. Sternberg, who makes his way through the world with a twinkle in his eye, told him, “If George Steinbrenner can live in Tampa and run the Yankees, I can live in New York and run the Rays,” he says. Instead, Silverman moved to Florida. Then Sternberg asked him if he had friends who might also want to get involved.

Silverman did. One of them, Andrew Friedman, had been working in finance while trying to get a job in baseball. Sternberg figured that Friedman, who briefly played at Tulane, could handle baseball operations. Brian Auld, a former teacher in East Palo Alto, Calif., working toward an M.B.A., would help on the commercial side; he and Silverman had attended high school together in Dallas. None of them had worked for a sports team or run a business of any kind. But that, Sternberg told them, was the point. “You’ll fail miserably for five years,” he said. “You might be a disaster. But you’re smart. You’ll figure it out. And when you do, I’ll have you for the next 20 years.”

That mind-set, that failure was fine — even encouraged, as long as it was in the service of learning — permeated the franchise. It allowed Rays executives to take risks that led to innovations, on the field but also off it. (The Rays were the first major-league franchise to abandon cash payments for tickets and go fully electronic, for instance. And to try to establish loyalty with emerging fans, they provided free uniforms for area youth leagues, outfitting every team in an iteration of a Rays shirt.) Some of their early attempts at learning the business were laughable. Friedman wanted to claim another team’s castoff player from the waiver wire, but he didn’t know how. Among the candidates he and Silverman interviewed to manage the Rays were the Hall of Famer Mike Schmidt and Alan Trammell, who would also be inducted years later. “How do you interview someone to be a major-league manager?” Silverman wondered. “What do you even ask them? I remember being very scared that I was going to say something that would just expose my complete lack of experience.”

In the end, they settled on Joe Maddon, a coach for the Los Angeles Angels, who had never advanced beyond the low minors as a player. A baseball lifer with the mind-set of a contrarian, Maddon says he would have been “absolutely disappointed” if the Rays hadn’t hired him. “It was the spot — the one spot — where my baseball sensibilities would be appreciated. You could try things. Everything was in play. And that became a huge part of our success.”

Friedman hired two stats geeks, James Click and Chaim Bloom, who had written for the website Baseball Prospectus. (Both would go on to become general managers of major-league teams.) The analytics group that took shape would crunch numbers, then offer recommendations. For example, they considered pitch framing, a catcher’s talent for making balls look like strikes, to be so critical that the Rays sought out masters of the art, like the journeyman José Molina, then kept them in the lineup no matter how poorly they hit. “When we had Molina,” Auld says, “I think we thought he was like the third-most-valuable player in all of baseball. And he was hitting around .200, and he didn’t like chasing passed balls, and all our fans hated him, and we just put him out there every day.”

The shift, relocating fielders to the areas of the field where, according to the data, individual batters tended to hit the ball, saved more runs. Pitchers hated the idea that a grounder would occasionally dribble past where the shortstop traditionally stood. “But then rockets are hit right over the mound, a surefire hit, and the shortstop is standing right there,” Silverman says. “And it took a little time, but eventually they said, ‘I’m willing to accept that I’m getting the benefit of this, even though it doesn’t feel natural.’”

Sternberg not only encouraged those experiments, he also insulated his employees from unwelcome consequences. “Whenever we wanted to try something a little bit crazy, Andrew would always say, ‘Well, in a couple of years we’ll all be pumping gas anyway,’” Click told me. “But because of Stu, we didn’t have to worry about that. So we could say, ‘We’re going to take the long view and try to put this organization in a position to succeed for 10 or 15 years.’ There’s not a lot of places in sports where you have the ability to do that.” And as it turned out, Silverman, Friedman and Auld didn’t need five years. They reached the World Series in three.

Before long, the Rays had baseball’s best defense. Because defensive statistics are nearly always undervalued in players’ salary arbitration hearings, the team was saving runs far more cheaply than it would have cost to create them. Later, the Rays would sometimes use a reliever to pitch no more than once through the opposition’s lineup before replacing him with a starter who could then work deep into a game. The Rays didn’t invent all the tactics that became associated with the use of analytics, but, Silverman says, “we leaned into them harder than other teams did.”

And the Rays kept churning their roster. Alone among league owners, and perhaps among franchises in any sport, Sternberg values a win at some future date as much as he values one in the present. He never minded Friedman’s trading an established star for prospects. That’s a strategy often employed by bad teams that are hoping to improve in the coming seasons, but not by those chasing a World Series. “The amount of risk aversion in professional sports, the fear of making a mistake because the present is valued so much, is enormous,” says Erik Neander, who became general manager in 2016 following Friedman’s departure for a similar position with the Dodgers two years earlier. “Stu has given us the freedom to make the trade that might not look like it makes sense in the present — the ‘delayed-gratification transaction.’ That’s the magic.”

Most low-revenue franchises have the wherewithal and good fortune to construct a championship contender perhaps once a generation. That means fans of the Kansas City Royals, the Miami Marlins and the Pittsburgh Pirates, to name three examples, spend long stretches of their lives following losers. They celebrate a trip to the World Series about as often as they attend a high-school reunion. When one of these potentially magical seasons emerges, the executives who run those franchises do what they can to increase the odds of getting there, even if it means pillaging their farm system to trade for a veteran who might make the difference.

That is antithetical to how Sternberg thinks. “You always hear the expressions: ‘We’re going for it! We’re all in!’” Sternberg says. “We’ve never done that. We’ve never been ‘all in.’ We might be up by three games in the standings in July, but we’ll trade one of our top players if it will make us better in the next few years.”

The trade that sent the starting pitcher Chris Archer, a two-time All-Star, to Pittsburgh in 2018 was a typical Rays transaction. Tyler Glasnow, one of the players they received in return, was an intriguing pitching prospect whose yearly earned-run average never got below the mid-4s, mostly because he did not consistently throw strikes. Rays coaches told Glasnow that his darting pitches would be successful if he stopped trying to locate them too precisely. “I got to the Rays,” Glasnow says, “and they were like: ‘Your stuff plays out. If you aim down the middle, with your characteristics, your extension, they’re not going to end up there. You’re going to miss bats.’”

Over the next five-plus seasons, batters on average hit below .200 against him. With his long hair and expressive demeanor, he became a fan favorite. But in December 2023, when Glasnow was a year away from securing a huge contract as a free agent, Neander traded him to the Dodgers for two more young players, Ryan Pepiot and Jonny DeLuca. Glasnow then signed a $136.5 million extension with his new team.

Pepiot replaced Glasnow in the Rays’ rotation. As I walked into a recent game in Tampa, I was surprised to see a fan wearing a uniform with Pepiot’s name on the back. Once inside, though, I saw plenty of fans in Rays jerseys that said “Glasnow,” though he himself hadn’t worn one in nearly two years. They struck me as a statement honoring a player who, by all rights, should have still been with the Rays — and could have been, if their business model had allowed it.

The Rays reached the World Series for the second time in 2020. It was the pandemic season, so the games were played at a single site, Globe Life Field in Arlington, Texas, and attendance was limited. They lost, to Friedman’s Dodgers in six games, but in the process gained additional respect around the country as “innovators in a sport often yoked by tradition,” as The Christian Science Monitor put it.

Back home, though, fans barely noticed. In 2022, the first season with no pandemic-era restrictions on crowd size, the team drew just 1.12 million fans, fewer than in 2019. “Stu is forced to reinvent every year,” says a major-league executive who requested anonymity because the league does not want officials with one team talking about another team. “And I think there is a huge fan-fatigue factor with that.” A franchise that relies on arbitrage strategies and quirky tactical advancements to overachieve year after year is an entertaining addition to any sport, but it is perhaps not as lovable to hometown fans. The last time the Rays made the playoffs, in 2023, their attendance for a wild-card game at Tropicana Field was just 19,704. It was the smallest crowd at a postseason game in a non-Covid year since 1919.

Of course, the proposition to fans would have been different if the Rays had managed to build a new stadium. In 2018, after a plan collapsed that would have put one in Tampa’s Ybor City neighborhood, the Rays applied their creativity to what was starting to feel like an existential issue. Because Florida summers are wet and oppressively hot, it had been assumed that any new venue would need a roof, which could add hundreds of millions of dollars to construction costs. But what if the team didn’t play in Tampa or St. Petersburg during the summer? Since 2005, when the Montreal Expos moved to Washington and became the Nationals, Montreal had been pining for a replacement. If the Rays could play in an open-air ballpark in Tampa in the spring and fall and escape to the far more temperate climate of the St. Lawrence Valley during the months between, they could reap the advantages of both markets.

The idea was met with incredulity from nearly everyone. But upon closer examination, it was logical — as logical, at least, as sending out a lineup of right-handers to face Mike Mussina. In June 2019, the league gave Sternberg approval to pursue it. “I am 100 percent convinced — and, more importantly, the other owners have been convinced by Stu — that this is best way to keep Major League Baseball in Tampa Bay,” Rob Manfred, the league’s commissioner, said the following February. But in January 2022, with the Rays coming off consecutive division titles, Manfred scuttled the plan without public comment. Sternberg called the development “flat-out deflating.”

Even into this season, though, Silverman still fantasized about making Montreal work. “If you ask fans if they want this four months a year or a dome all year, they might take this,” he said at the Yankees’ minor-league field, gesturing toward the timeless tableau of outdoor baseball in front of him. He pulled out his phone, swiped and scrolled, then showed me the screen. It still had Montreal on his weather app.

Last summer’s deal for a new stadium — with wide concourses, clubs, restaurants and enhanced suites — would finally have ended the decades-long saga. But the Rays would still have faced the formidable task of coaxing much of their potential fan base across one of the bridges that connect Tampa and St. Petersburg, which invariably clog with traffic on weekday afternoons. They would still be competing nightly with recreational opportunities at the beachfront and beyond. And prioritizing staying competitive year after year might never have satisfied fans who in recent years celebrated a Super Bowl victory and two Stanley Cups. In a sense, Sternberg figured out how to solve baseball. But he never managed to solve Tampa.

After the hurricane, Sternberg’s refusal to accept the terms of the original deal, which hadn’t been approved by the city, was perceived as a betrayal by St. Petersburg officials. “When we said we were not going forward with the project in March, they were clear they did not want to do anything with me,” Sternberg says. As months passed, the perception grew inside baseball that Manfred, backed by many of the owners who employ him, preferred that he sell the Rays. It seemed unlikely that Sternberg could handle the political maneuvering necessary to get financing for a new ballpark. And because Manfred had publicly dismissed the idea of Sternberg’s relocating the Rays to another market, Sternberg didn’t even have that as leverage.

There is also no love among fellow owners for the competitive model that Sternberg’s team has constructed, one in which the sport’s behemoths not only often find themselves chasing the Rays but also — through a tax-and-fund system that the league uses to help offset imbalances in team revenues — actually subsidizing Sternberg to beat them. As the major-league executive put it to me, rich teams like the Yankees were fed up with paying the Rays to finance their competitiveness. Finally, with Major League Baseball using the widening gap between the richest and poorest clubs as an argument to cap team payrolls, Sternberg’s track record is an inconvenient counterexample. “He’s put a real wrinkle into the argument of competitive balance, and how teams in the bottom five in revenue have no chance of competing,” Friedman says. “He has debunked that in a way that is not helpful to that overall narrative.”

In early June, Manfred and baseball’s owners convened for meetings on Manhattan’s West Side. That Thursday, just after the final session of the three-day gathering, Sternberg suggested we meet at a tearoom inside the Church of Sweden, off Fifth Avenue. Sternberg ordered strawberry-rhubarb pie. He sat down with it and told me that the issue, clearly, was money. “There are strong feelings at M.L.B.,” he said, “especially because we are revenue recipients. If we were revenue-payers, or neutral, people would be concerned for us. But they wouldn’t be concerned for themselves.” At that point, he said that he was open to selling the Rays and that he seemed to have a buyer.

That buyer, Zalupski, was a robust contributor to the presidential campaign of Florida’s governor, Ron DeSantis. If the $1.7 billion sale is approved by league owners in the coming months (a vote has not yet been scheduled), having a wealthy, politically connected owner may help get them a stadium. Sternberg’s departure will indisputably be a loss for baseball, which historically has managed to limit the tenure of freethinking, maverick owners — like Bill Veeck, who invented the exploding scoreboard and once sent a 3-foot-7 player up to bat. It will also, for better or worse, make the Rays feel a lot more like every other team. It is easy to imagine a future in which a relatively flush version of the franchise signs 29-year-old outfielders to nine-digit contracts and aspires to, every so often, push past the wealthy teams from the biggest cities. While some Rays fans might find that idea appealing, it is hard to argue that it would result in, say, close to 900 wins over a decade. “Stu has set a high bar for sustained success,” the Dodgers’ Friedman said. “It will be really challenging for anyone else to match that.”

The day I saw Sternberg in New York, his Rays defeated Texas to win their third successive game. As of early August, they were still in contention to once again make the playoffs and, against all odds, give Sternberg a valedictory championship. None of the other owners I spoke with would begrudge him that; Sternberg is almost uniformly viewed with affection. But several acknowledged that they were frustrated by his Rays’ lack of fan support and had grown tired of the unfavorable comparisons between their own teams and one that spends so little and wins so much. I got the sense that none of them will be unhappy to see him go.