Yankees Should Adjust Free Agency Approach as One of Players' Top Destinations

A player poll named the Yankees as one of the best teams to play for, and they should flex their standing within the league a little more.

GM Brian Cashman needs to start using the Yankees' reputation to his advantage more often. | Jayne Kamin-Oncea-Imagn Images

The Yankees haven't won a World Series since 2009. 16 years is essentially a lifetime for those Bronx faithful who had become accustomed to winning in the mid-to-late 90's, and now have watched their team struggle to hoist the Commissioner's Trophy just once these days.

Droughts aside, if there is one thing that the Yankees have kept, it's their standing in the league among players. They're still a destination even if, from the outside looking in, it seems like Hal Steinbrenner has a reluctance to add stars at the rate his late father, George, did.

According to a recent player poll, The Athletic's Dennis Lin reported on Wednesday that 93 players were asked about which teams have the best reputations. The Dodgers came first, as they usually do in everything these days. 59 players mentioned them. The Yankees came in at second with 38.

Despite the Yankees' championship drought, the Bronx is clearly still an enticing destination for MLB players. | Vincent Carchietta-Imagn Images

The reasons for that are varied. One mentioned that he rehabbed with the Yankees in the minors and mentioned they treated him "amazingly." Another said they make every attempt to be a "class organization." Another said that they believe the front office has the players' backs.

"I think it comes down to the players feeling like the owner and the front office have their backs and they're willing to do what they need to do to keep their players happy," one player said of the Yankees in that poll for The Athletic.

With the glowing reviews rolling in, it's clear that general manager Brian Cashman and the rest of the Yankees front office need to capitalize on their reputation more often.

Yankees must use their reputation to lure stars

If the Yankees are still the place to be, it wouldn't hurt for them not to enter a season with some holes on their roster. Despite being the third-highest spender in baseball and one of three teams with a payroll north of $300 million, every year it feels like they enter the season already looking to the deadline to fill out their roster and use the winter accordingly.

With money coming off the books, and both Gerrit Cole and Carlos Rodón heading to free agency after the 2028 season, fortifying the rotation becomes paramount the closer that the Yankees get to their two bulldog starters potentially heading elsewhere. What better way to get ahead of that than by landing the biggest fish of the winter, Tarik Skubal?

Even if they don't trade for him, Tarik Skubal should be among the Yankees' top free-agent targets this winter. | Junfu Han / USA TODAY NETWORK via Imagn Images

They'll have some competition for Skubal, but, with room to work with, with the potential loss of David Bednar, Jazz Chisholm Jr., Trent Grisham, and Paul Goldschmidt, there's no reason they can't have the top offer on the table for him. They are the Yankees after all, and it wasn't that long ago that they had the biggest bid by a mile for their current ace, Cole.

Another name to watch could be Michael King if he opts out of his deal with the Padres.

King is having another solid season, posting a 3.33 ERA in 92 innings pitched so far, but one red flag for him at the moment is his drop in strikeout rates year after year. King had a 10.42 K/9 with the Padres in 2024, which fell to 9.33 in 2025, when he pitched just 73 1/3 innings, and had an even more dramatic drop-off this season. He owns a 7.63 K/9 in 2026. At that point, it could be better to stick with Will Warren.

The Yankees will also need an infielder if they don't bring back Chisholm. Luis Arráez will be available this winter, and his glove has finally caught up to this bat. He isn't the liability that he once was.

Bo Bichette is another name. Although after a tough year with the Mets, where he has posted a 93 wRC+ thus far, he may decide to stick with his club, which is paying him $42 million. The smart move may be to avoid opting out in his case.

Regardless of who the Yankees pursue, it's clear that their reputation is a tool that should be used more frequently. The most well-known baseball franchise of all-time is a household name for a reason, and it's time to start acting that way again.