As the New York Yankees prepare for the beginning of the 2024 season, they are still looking to improve the pitching staff.
The Bronx Bombers already missed out on signing two-time Cy Young Award winner Blake Snell, who went to the San Francisco Giants on a two-year, $62 million deal with an opt-out after the first year. However, there is another option out there for the Yankees - one they know well.
Jon Heyman of the New York Post revealed that the Yankees have re-entered negotiations with free agent left-hander Jordan Montgomery. There is a gap between what each side wants, but talks have begun nonetheless. According to Heyman, Montgomery is using the seven-year, $172 million contract signed by Aaron Nola as a base value.
The 31-year-old Montgomery was a reliable starter for the Yankees from 2017 to the middle of 2022, being a durable innings-eater that was able to handle the bright lights of New York. However, the Yankees didn't think his ceiling was particularly high, and made a now-notorious deal with the St. Louis Cardinals at the 2022 trade deadline, acquiring outfielder Harrison Bader in return.
Montgomery blossomed into a top-of-the-rotation arm with St. Louis, assisting them in the 2022 stretch run before being traded again at the deadline in 2023; he recorded a 3.31 ERA in a Cardinals uniform.
After being traded to the Texas Rangers at the 2023 deadline, Montgomery continued to prove his former team wrong by being a driving force towards the Rangers' first World Series title. He logged a 2.79 ERA in 11 regular season starts before enjoying a fantastic postseason; in six appearances, he went 3-1 with a 2.90 ERA and tallied 17 strikeouts against just five walks.
Seeing what their former homegrown pitcher has become, it makes perfect sense for the Yankees to pursue a reunion. Adding a high-pedigree starter has gone from a luxury to a direct need for the Bronx Bombers, due to ace Gerrit Cole missing at least a month or two with elbow inflammation.
Also, while the Yankees believed Snell was too risky to sign, Montgomery doesn't carry nearly as much of a risk; assuming Montgomery would sign a short-term, higher AAV deal with opt-outs like Snell, the Yankees wouldn't be penalized as much by the luxury tax compared to signing Snell, while they wouldn't have to sacrifice a draft pick to sign Montgomery either.
Currently, both parties are far apart in talks, but the Yankees absolutely should continue negotiations with Montgomery, as his past experience pitching in the Bronx and recent breakout make him an ideal addition to a team that is going all-in for a World Series title.
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