Three free agents the Yankees must sign to make World Series return

The days of George Steinbrenner seem like a distant memory in the Bronx. The New York Yankees last won the World Series in 2009, while he still stood at the helm. But most, if not, all Yankee fans still openly echo his philosophy, believing there is no such thing as a good season; you either win or you lose. If you did not win, then you lost. And if you lost, how can it be a good season?

2025 was just the latest reminder that the shadow of The Boss has further diminished along with his all or nothing mantra. Still, it wasn’t the fact that the Yankees lost that was most disheartening, but the embarrassing way their season collapsed. The Yankees made it to the postseason, yet they never truly looked like they belonged there.

If the Yankees are going to recapture at least some of their once-dynastic dominance, they will need to start with the free-agent market. Here are three free agents who might best fit the Yankees’ needs.

OF Kyle Tucker

With Cody Bellinger and Trent Grisham heading into free agency, the Yankees are left with a massive opening, giving the team an opportunity to upgrade a crucial position. With 30-plus HR power outside of Yankee Stadium, ample speed, solid bat-to-ball skills and a keen eye at the dish, Tucker has the potential to be a transformational upgrade.

In an injury-hampered down year — though it’s hard to call it a down year — the former Gold Glover slashed .266/.377/.464 with 22 home runs and 25 stolen bases in 500 at-bats. His 162-game average over his career is 273/.358/.507 with 31 home runs, 25 stolen bases and 103 RBI.

1B Josh Naylor

Yankee fans and Gerrit Cole alike might not be fond of Naylor, but the Yankees desperately need a hitter who can excel in the postseason and doesn’t struggle to make contact, and Naylor is one of the few proven free agents who fit the bill. This year, Naylor slashed .295/.353/.462 with 20 home runs and a stunning 30-2 stolen base record. And in the Bronx, his stealthy, left-handed power (hit 31 home runs in 2024) could be a game-changer. In the 2025 playoffs, Naylor went 16-for-47 (.340) with three home runs and four walks — though this performance included a jump interference. 

The main problem with adding a first baseman is that Ben Rice appears to have already won the position. However, if he can be further developed as a catcher, Rice could take over for Austin Wells, who has been unproductive in the batting order. This would alleviate an important dead spot in the lineup while giving the Yankees an essential opportunity to improve. If the Yankees can’t find sufficient room to improve, they won’t win. Other options include Munetaka Murakami and Pete Alonso, but acquiring either star may be unlikely. 

SS Bo Bichette

Bichette has been derided for being one of, if not, the worst defender at shortstop. However, the Yankees currently have a shortstop — Anthony Volpe — who has struggled with both bat and glove. This season, Bichette posted a WAR value of 3.4 compared to Volpe’s 1.7. Still, the stats might not do either player justice as both dealt with injuries.

Bichette is coming off a year where he hit .311/.357/.483 with 18 home runs in 582 at-bats. He comes with proven 25-plus HR potential and could slot seamlessly into the lineup in front of Aaron Judge. While Bichette might not be a defensive improvement, he is an improvement nonetheless.