With the retirement announcement of former star reliever David Robertson this week, the amount of active Major League Baseball players to have won a World Series ring as a member of the New York Yankees drops to the lowest possible amount – zero. Nil. Zilch. Nada.
As every Yankees fan will know, the franchise is in what is, by its own high standards, a vast yawning chasm of a World Series drought. The team has not won the Fall Classic since the 2009 season, its only title in the 21st century, and only once since then (2024) have they even made it to the Series at all. Theirs is now a futility streak longer than the 1962-1977 stretch, and is now the second-longest such stretch in Yankees franchise history, behind only the quiet years of 1978-1996.
And precisely because of that, every player involved in the 2009 title is now out of the majors.
No Yankees Still Standing
Because the Yankees’ most recent World Series championship occurred 16 years ago, a player who appeared on the 2009 roster would now be in his late 30s or 40s, and most such players have retired. With Robertson’s exit, that era’s last direct on-field bridge to the 2009 title has gone.
One player is at least playing. Long-time Yankees enigma Robinson Cano is still playing baseball, appearing for the Diablos Rojos del México of the Mexican League, and is doing well, hitting .372/.426/.573 with 14 home runs and 86 RBIs in 85 games last season. He even won the MVP award of the championship series, as befits the best player on the best team.
Cano, though, is 43 years of age, and never coming back to the majors. Unless Robertson pulls a swerve and signs back up for the second half of next season, neither will he. And everyone else – from Congressional candidate Mark Teixera to the best left fielder ever Brett Gardner – are all well into their post-playing career lives.
An end to the drought, then, is more than overdue.
Time For The Drought To End
The Yankees won 94 regular season games last season and triumphed over the great rival Boston Red Sox in the American League Wild Card Series by two games to one, but lost to fellow AL East rivals the Toronto Blue Jays in the ALDS. The fact that the Blue Jays went on to win the World Series was of scant little consolation. In an all-or-nothing environment, 94 wins was nothing.
Having lost out on Juan Soto in the signing period of winter of 2024, and coming up short on the field yet again in 2025, it was hoped that the Yankees would put the hammer down in the offseason and make some marquee acquisitions to put themselves in the American League’s driving seat. Edwin Diaz, for example, was one such target. But amid public grumbles about payroll concerns, the Yankees have instead had an extremely quiet offseason, losing out not only on Diaz to the free-spending Los Angeles Dodgers, but also losing their own bullpen battery of Devin Williams and Luke Weaver to the cross-town rival New York Mets. The Yankees will instead mostly be running it back, despite “it” not being good enough last year.
Even with the quiet offseason, the Yankees are considered by some to be favorites to win the American League in 2026. With Aaron Judge playing his way onto the Mount Rushmore of baseball’s all-time best hitters, Cody Bellinger returning as a free agent, Gerrit Cole returning from injury and a potential breakout season for Ben Rice forthcoming, maybe the Yankees can power their way through. You would think, though, that a drought this long would bring about some greater urgency.
No Active Players Have Won a World Series With the Yankees