The Yankees at this point in the offseason are now in search of starting pitching, after missing out on Yoshinobu Yamamoto who signed a 12-year $325 million contract with the Dodgers. The Yankees made a very good effort, but now they have to pivot. I will be going over my preferred options for the rest of the winter heading into 2024.
Bring Back a familiar face
The Yankees could look for some familiarity in Jordan Montgomery. Montgomery fresh off a World Series ring with the Texas Rangers, could be a very interesting signing for the Yankees. Coming off a great Postseason as well, the Yankees could seek his services. He doesn’t have the vast market that was expected, teams like Boston, Baltimore, and Chicago (NL) have not reportedly been very involved in trying to sign him. I think now would be the time for the Yankees to get him back in pinstripes. Though he will be more expensive than he would’ve been previously, he is well worth the price as he can be a major addition to the rotation especially if Carlos Rodon regains form.
Contract: 6 Years, $150 Million
1-Year Prove it?
Frankie Montas missed almost all of the 2023 season, pitching in just one game at the end of the season. Since the end of the regular season it’s been talked about as almost a foregone conclusion that Montas would end up returning to the Yankees on a 1-year incentive laden deal. This could work out very well for the Yankees. Montas was acquired in a 2022 deadline deal that sent him and Lou Trivino to the Bronx. Montas however struggled due to various arm injuries. He will be healthy going into 2024, and if he regains the form we saw in Oakland before the trade, the Yankees will be very happy with the production in the middle of the rotation.
Contract: 1-Year, $13 Million
Bolster the Bullpen
The Yankees have reportedly been very involved in the bullpen market, particularly free agent reliever Robert Stephenson. Stephenson broke out this season for the Tampa Bay Rays and he is arguably the best reliever on the open market. And the Yankees have reportedly wanted to build a “super-charged bullpen” Stephenson certainly helps them with that. Adding Stephenson to an already established and very good bullpen would be a very good move for the Yankees, providing them with more quality depth.
Contract: 2-Year, $15 Million
Though the Yankees have a multitude of options available via trade and free agency. Dylan Cease, Corbin Burnes, and Shane Bieber through trade, Blake Snell, Shota Imanaga, and Yariel Rodriguez among others are also available. I believe that the Yankees will finish off their winter with signing Montgomery, Montas, and Stephenson. The trade targets available may cost too much in prospect capital that the Yankees aren’t comfortable parting with. Having already parted with multiple pitching prospects in the Juan Soto trade, I believe this is the most likely outcome.
Rotation Options and Bullpen:
RHP Gerrit Cole
LHP Carlos Rodón
LHP Jordan Montgomery
RHP Frankie Montas
LHP Nestor Cortes
RHP Clarke Schmidt
Bullpen:
RHP Clay Holmes
RHP Jonathan Loaisiga
RHP Robert Stephenson
RHP Ian Hamilton
RHP Tommy Kahnle
LHP Victor Gonzalez
RHP Luis Gil
BS Reports 
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