The New York Yankees haven't won a World Series since 2009.
Granted, 15 years isn't a long drought compared with many other teams. The Cleveland Guardians (formerly Indians before choosing one of the worst possible names in 2021) won their last title in 1948. It could always be worse.
But these are the New York Yankees. After their historic late-1990s run—four championships in five years from 1996 through 2000—plus two more trips to the Fall Classic in 2001 and 2003, they've won it all just once.
The last time the Yankees went this long without a ring was the period of time between the 1978 and 1996 seasons. Their failure to make the postseason in 2023 marked the fourth time their season ended in September since that 2009 World Series, with the Bronx Bombers missing the cut in 2013, 2014, and 2016 as well.
The last time the Yankees missed the postseason four times within a 10-year bloc was the stretch from 1982 through the strike-shortened 1994 campaign, when only two teams from each league qualified.
The 2010s were the first decade since the 1910s in which the Yankees didn't play a single World Series game. For a fanbase so often described as being spoiled by success, repeated playoff losses—often to the hated Houston Astros—leave a bad taste in the mouth.
Through it all, from the late-1990s glory days up to now, there's been one constant. General manager Brian Cashman, the longest-tenured front-office leader in baseball, has run the show since 1998 after having joined the organization as an intern in 1986.
Sportswriter Andy Martino, in his recently released history The Yankee Way: The Untold Inside Story of the Brian Cashman Era, traces Cashman's path from up-and-comer to captain of the largest superyacht in professional sports.
Unsurprisingly for Yankees fans familiar with their team's history, Cashman was not the main character in the story of the franchise's most recent dynasty. Neither was owner George Steinbrenner. It was Cashman's predecessor, Gene Michael, who operating on his own accord during Steinbrenner's suspension from baseball (for paying a gambler to dig up dirt on star outfielder Dave Winfield) laid the foundation for the late-'90s Yankees.
Sure, Cashman pulled off big trades after taking the helm in 1998, and sure, he had to contend with an increasingly involved owner after the dynasty ended. But after being left to his own devices, with the roster he inherited from Michael—which included Derek Jeter, Paul O'Neill, Andy Pettitte, Jorge Posada, Mariano Rivera, and Bernie Williams—either graying or gone, he won just one title.
Martino describes Cashman as having done just about everything—instituting advanced statistical analysis in front-office decision-making, managing the array of egos in the Yankee locker room, taking special note of the impact of a player's mental state on his performance—in pursuit of championships. But it hasn't worked. And maybe it's because Cashman is an unremarkable strategist who won the lottery by being with the Yankees in the right place and at the right time.
During Steinbrenner's absence from baseball, Michael was able to build up the organization's farm system. That was not the case when Steinbrenner oversaw front-office operations.
By the late '80s, before Steinbrenner's suspension, "the Yankees' player development apparatus was ahead of its time." The problem, said Bill Livesey, the team's then-scouting director, was that "we traded them all away. With the exception of [Don] Mattingly, we traded them all away."
With Steinbrenner out and the franchise under Michael's management, the front office "learn[ed] to hold on to our core guys," Livesey told Martino. "We traded for Tino [Martinez], David Cone, and others. But this time we tried to have enough prospects where we could say no to trading the core guys—the Jeters, the Posadas, the Bernies, the Marianos, Pettittes. And we did say no to trading those guys."
Cashman learned that lesson, but perhaps too well. Refraining from trading players in the Yankees' farm system cost the team its chance at pitching aces like Cliff Lee in 2010—Cashman refused to part with either Ivan Nova or Eduardo Nuñez—and Jacob deGrom in 2018 (Miguel Andújar or Gleyber Torres constituted too high a price tag).
Lee would finish in the top 10 in Cy Young Award voting three times between 2010 and 2013, and deGrom, of course, put together one of the greatest pitching stretches in baseball history from 2018 through 2021. Nova and Nuñez never found their footing and washed out of the league, and the Yankees ultimately cut Andújar after he regressed following a productive rookie season. Torres, the team's current second baseman, is in the midst of the worst season of his career after seeing his play decline nearly every year since his debut.
Interestingly enough, Martino does not include that information in his book.
He does include a sympathetic portrayal of Cashman's struggles with Steinbrenner, who took a more active role in the team's baseball operations after the Yankees stopped winning it all each year. And some of Cashman's instinctive decisions were correct.
Following a 2003 season in which a sapped Yankees team lost the World Series to the Florida Marlins, the GM came to terms with then-28-year-old Montreal Expos outfielder Vladimir Guerrero. Steinbrenner had other ideas, pursuing a 34-year-old Gary Sheffield instead. Needless to say, while Sheffield found some success in his two years and change with the Yankees, Guerrero was simply a better player. He finished in the top 10 in Most Valuable Player voting each year from 2004 through 2007, winning the award in his first season with the Anaheim Angels.
But other instances of Steinbrenner's heavy-handed involvement proved fruitful.
When reigning MVP Alex Rodriguez opted out of his contract after the 2007 season, Cashman "did not recommend re-signing" him, wanting instead to "spread that money around on the roster." Steinbrenner intervened, signing A-Rod to a new deal and retaining a player who ended up carrying the Yankees to the 2009 World Series—the only championship the team has won since Cashman began building out his own roster.
Cashman would continue to hew to that idea of "spread[ing] that money around on the roster" over the next decade-plus, often to baleful effect. Declining to offer standout hitter Bryce Harper—now a two-time MVP—a contract after the 2018 season, Cashman ended up trading for a 35-year-old and washed-up Josh Donaldson, alongside utility infielder Isiah Kiner-Falefa, three years later.
Harper made $27.5 million in 2022. Donaldson and Kiner-Falefa combined for $26.45 million that year. Harper is one of the best players in baseball. Donaldson spent a disappointing year-and-a-half on the Yankees and is now out of the league, while Kiner-Falefa made it through two full years in New York before hitting free agency. The Yankees didn't try to re-sign him.
That's not in the book, either.
Martino tells the reader at the outset that "this was not [Cashman's] book." At the same time, he continuously notes that Cashman will likely end up in baseball's Hall of Fame.
He quotes Oakland Athletics front-office executive Billy Beane—he of Moneyball fame—as claiming Cashman is "the greatest executive in the history of the sport."
"He has four championships and the longest tenure," Beane told Martino. "It's not unlike Tom Brady's career, from an executive standpoint. He is the Tom Brady of GMs."
A better comparison would be Jonathan Kraft, son of New England Patriots owner Robert, who has worked in the organization since 1994. Sure, he has the rings and the tenure. But he's really just along for the ride.
The Yankee Way: The Untold Inside Story of the Brian Cashman Era
by Andy Martino
Doubleday, 320 pp., $30
Zach Kessel is a William F. Buckley Jr. fellow in political journalism at National Review.