From 1998-2007, the Tampa Bay Devil Rays, a Major League Baseball expansion team, lost 90-plus games every season, finishing fourth in the division once and dead last in the other nine. It was as if they were in baseball hell.
When Rye resident Stu Sternberg took ownership of the team in 2005, he began exorcising their demons. A major step in the overhaul was removing “Devil” from the team name after the 2007 season.
Since the rebrand, Tampa Bay won the third-most games in baseball – behind only the Yankees and Dodgers – made the playoffs nine times, won four division titles, and reached the World Series twice, all the while following Sternberg’s philosophy of buying low and selling high.
Now, the former Wall Street trader and Goldman Sachs partner has cashed out. In October, Sternberg sold the Rays for $1.7 billion, 20 years after his ownership group acquired the team for $200 million.
In a recent interview with The Record, Sternberg said far less important than the $1.5 billion return on investment are the relationships and experiences he cultivated along the way.
Rays of Hope
Sternberg grew up loving baseball. Born in 1959, two years after both of New York’s baseball teams relocated to California, he rooted for Sandy Koufax and the Dodgers from the age of three. When the Mets were added as an expansion team in 1962, he eventually became a fan, holding season tickets in the 1980s.
He built a career in finance and moved his young family to Rye 33 years ago. His four kids – Sanford, Jake, Natalie, and Ella – all graduated from Rye Country Day and moved out, but Sternberg and his wife, Lisa, remain rooted in their Bellevue Ave. home.
“I grew up in a part of Brooklyn, in Canarsie, where people grew up there, then just sort of left,” Sternberg said. “So, it was a real nice change of pace to come up to a place like Rye and see that people have been here for a couple of generations of families, and to know that people care about the area.”
Even after he became owner of the Rays, Sternberg spent many years managing another ballclub — this one in Rye. Second Chance, a men’s softball team, was led by Sternberg, who formed the lineups, played centerfield, and, according to teammates, never once acted better than anyone else on the team.
Since his family’s arrival in 1992, Sternberg has admired the continuity and atmosphere of community in Rye.
“Even though there’s been change over the years, it hasn’t been dramatic,” Sternberg said. “And I think there’s a real sense of place. I think the people who live in the community want to be part of something and like to see familiar faces.”
Sternberg brought that same kind of care to the Rays, and others quickly took notice. As MLB competitors watched the Rays succeed, they poached key contributors in hopes of replicating Tampa Bay’s winning culture. Many of those departures helped improve other franchises. But the personnel losses didn’t subtract from the Rays’ win totals.
“One thing we’re proud of is we’ve got five of the 30 guys running teams right now,” Sternberg said. “You know, presidents of baseball operations who came from our organization, and a number of managers, and there have been other guys who run baseball teams. From 2008 on, those young guys who came in with us have spun out to run their own baseball departments for other teams as well.”
Mark to Market
After 25 years working on Wall Street, Sternberg built the Rays’ front office around executives who shared his economic acumen, more so than his passion for baseball.
Andrew Friedman, a Bear Stearns analyst, became the Rays general manager. Matt Silverman, one of Sternberg’s fellow Goldman Sachs partners, became co-team president along with Brian Auld.
“The nice part was, it was all new to us,” Sternberg said. “We didn’t have any preconceived ideas or anything, and so we were able to work with a fresh slate. And it was easy to teach them and work with them, and use the Wall Street valuation approach, a mark-to-market approach, which was something that hadn’t been done, really, in baseball before.”
Former Oakland A’s general manager Billy Beane’s cost-efficient “Moneyball” philosophy was popularized by Michael Lewis’ best-selling book in 2003 and the movie starring Brad Pitt in 2011. But Oakland’s small-market success never reached the heights of Sternberg’s Rays. The A’s never won a game in the American League Championship Series and have since returned to mediocrity, with 100-plus loss seasons in 2022 and 2023.
Under Sternberg, the Rays had nine seasons with 90-plus wins and claimed two American League pennants.
While the Yankees and Dodgers both eclipsed the $300 million-mark last season, Tampa Bay’s 2025 payroll was $88 million. The team never spent $100 million on a roster.
“If all you have to cook is corn and eggs, you make the best corn and eggs you possibly can,” Sternberg said. “When we came in, we had a strong sense we would do a lot better, because quite frankly, you couldn’t do much worse. But we never anticipated having the kind of success that we had for such an extended period of time.”
Silverman and Auld, who were childhood friends, worked alongside Sternberg for the entire 20 years. Friedman left Tampa Bay after the 2014 season to run the Dodgers’ baseball operations. Through a combination of Friedman’s brilliance and the Dodgers’ league-leading payroll, Los Angeles has been to five of the past nine World Series, winning championships in 2020, 2024, and 2025.
While Sternberg would have preferred a different outcome in 2020, when the Dodgers beat the Rays in the World Series, he’s followed Friedman’s ascension with pride.
“It was amazing,” Sternberg said the morning after Los Angeles’ 18-inning win over the Toronto Blue Jays in Game 3 of the 2025 World Series. “Andrew’s our guy.”
The Rays’ best players have gone on to succeed elsewhere as often as the front office stars have, but each departure created room for budding new talent that kept the team competitive without breaking the bank.
Six Degrees of Chris Archer
The headwaters of Tampa Bay’s ever-flowing fountain of youth is deft drafting. From September 2010 to June 2012, every Rays starting pitcher was drafted by the team, spanning a major-league record 232 games.
When promising minor leaguers become proven big-league contributors, the Rays typically trade them to a team willing to dole out a lucrative, multiyear contract. Scrolling the list of names in Tampa Bay’s transactions is like playing a game of “Six Degrees of Kevin Bacon,” orchestrated by Sternberg.
For instance, look at the web of connections that stems from the 2011 trade for Cubs minor-leaguer Chris Archer. His MLB debut for the Rays in 2013 snapped the team’s two-year streak of homegrown starting pitchers. He finished third in rookie of the year voting (Rays teammate Wil Myers won the award) and played in two All-Star Games. That alone makes the acquisition a resounding success.
But why settle for one All-Star today if you can turn him into two All-Stars tomorrow? The Rays sent Archer to the Pirates in 2018 for pitcher Tyler Glasnow and outfielder Austin Meadows. The next year, Meadows represented the Rays in the 2019 All-Star Game.
Glasnow made an even bigger impact. In his first month with the Rays, he won AL Pitcher of the Month. At the end of his rookie year, he started two games in the American League Division Series. In his second season, he started a decisive Game 5 of the ALDS, then two games in the World Series against the Dodgers.
Glasnow also started playoff games in 2022 and 2023, then the Rays traded him to Los Angeles. In return, they received Ryan Pepiot, Tampa Bay’s Opening Day starter in 2025. And the never-ending chain of dominoes plows ever onward.
“It wasn’t like it was just done cold and hard,” Sternberg said of the team’s penchant for wheeling and dealing. “You had to take a lot of things into consideration. But the most important thing was, we knew who we were and who we weren’t. We weren’t a team that was going to be able to spend $100-plus million, $200 million a year, and we had to work within our confines.”
Building a winning roster isn’t just about finding hidden gems, but also creating the conditions they need to succeed. From 2006 No. 3 overall pick Evan Longoria, to 2020 ALCS MVP Randy Arozarena, to 2025 All-Star Junior Caminero, the Rays consistently got more out of their players than any team in baseball.
But how?
“It really all starts with the people, because at the end of the day … you have a uniform, and you have a ballpark,” Sternberg said. “Then it’s, how do you fill the uniform? And who are the people selecting those players? How are they getting trained? How are they getting treated? And how are they meshed together?”
Just as important as knowing when to acquire players is knowing when to move on. And for Sternberg, the writing was on the wall last season.
Moving Right Along
Even when the Rays’ franchise debuted in 1998, their home, Tropicana Field, was in need of upgrades. Sternberg was in the process of developing a new, $1.3 billion stadium in St. Petersburg, Florida, last year when things went from bad to worse. In October 2024, Hurricane Milton ripped most of the roof off of “The Trop,” forcing the Rays to play their 2025 home games at George M. Steinbrenner Field, the Yankees’ spring training home in Florida.
Keeping the team in Tampa Bay suddenly came at a higher cost. Sternberg said that’s a major reason he decided to sell the team to a Florida-based ownership group.
“I’m a pretty pragmatic guy, and you know, I had an amazing 20 years in the game, and it was just time to move along and give them all the role that was going to be ahead of us,” Sternberg said. “The difficulty for us was to get a new ballpark that was sorely, sorely needed in the area. It just was going to be difficult to happen in Tampa Bay.
“So, I found a guy in a group that was committed to trying to get that done, and I think they’ve got the right connections and the right support. My partners and I still have a small piece of the team, and we’re excited to see how they do going forward. But, you know, it’s in somebody else’s hands.”
Breaking ground on a billion-dollar stadium, and all the unexpected costs, politics, and decisions that come with it, may be a burden Sternberg is happy to avoid. But the unmatched thrill of being around the game of baseball makes his departure bittersweet.
“Having stepped away now, the most important moment was beating the Red Sox in Game 7 to get to the 2008 World Series, and there were some circumstances that led to us even getting to Game 7,” he said. “But to do that was probably the most rewarding – no, definitely the most rewarding – time owning the team, because we’d only owned them for a couple of years.
“We had the worst record in baseball for two years running before that, and to get to the World Series that next year was just incredible … I would tell you, I pinched myself every time I went on the field, or anytime I was able to be around the game.”
The ability to see two steps down the road was critical to Sternberg’s success on both Wall Street and in the MLB, yet for someone who’s made a living predicting the future, even he could use a break before deciding what’s next.
“The one thing I said to myself is that I didn’t want to make any decisions about future plans while we were waiting for the transaction to happen,” Sternberg said. “When the baseball season starts again, I’ll see how I feel about it … I started working at 18, and worked on Wall Street for 25 years, and baseball for 20 years. So, I’ll take a little time to just try to figure out if there is a next step.”
