The New York Yankees nearly acquired starting pitcher Jack Flaherty from the Detroit Tigers ahead of the 2024 MLB Trade Deadline, but the deal fell through due to medical concerns from New York's end. As a result, the Yankees saw Flaherty start two games against them in the World Series with the Los Angeles Dodgers. With the pitcher hitting free agency, the Yankees have been mentioned as a suitor, despite the previous medical concerns.

“Jack Flaherty, right-handed starter: There's a chance Flaherty doesn't reach $100 million, but doing so is enough of a possibility to warrant his inclusion in this tier,” Jeff Passan wrote. “He threw 162 innings in 2024, the most he had in five years, and booked a 5-to-1 strikeout-to-walk ratio. If the Washington Nationals decide to spend on an anchor for their rotation, Flaherty could make sense. And the Yankees — who killed a deal for Flaherty at the trade deadline out of concerns about his back — could be in again.”

The Yankees' priority is clearly trying to retain outfielder Juan Soto, who had the best season of his career during his one year in the Bronx. Still, there are some other needs the Yankees have to fill even if Soto does come back. The starting rotation is not necessarily in bad shape, especially with Gerrit Cole remaining on the roster for 2025, but the Yankees and other teams hold the position that you can not have too much pitching. It is known the Yankees like Flaherty as a player, and if he does cost less than $100 million, as Passan suggests he could, maybe he makes sense for them to sign.

Who else could the Yankees target this offseason?

We know Soto is the big fish, and the Yankees could be in play for Jack Flaherty. Are there any other players the Yankees could target, and in what scenario could they pursue those players? Passan outlined a few possibilities in Willy Adames, Pete Alonso, Teoscar Hernandez and Christian Walker.

Adames has made it known that he is willing to play third base on a contender, which opens up the possibility for the Yankees to get involved. It is unknown how Soto plays into this, if he does return to the Bronx, but it would seem unlikely with the contract that he could get. The same could be said for Alonso, as Passan mentioned that he is unlikely to sign before Soto with both New York teams' attention on him.

However, Passan had interesting things to say on Hernandez and Walker, specifically saying that the Yankees want Hernandez if Soto does not re-sign.

“Boston is in. So is Baltimore. And the Yankees want him if Soto doesn't come back, though he could have already signed by the time New York knows where it stands with Soto,” Passan wrote.

When it comes to Walker, the Yankees were the only team mentioned, and Passan noted that he is an ideal fit and could get a three-year deal.

It will be interesting to see the additions the Yankees make this offseason.