Yankees can't afford to miss on free-agent reunion after whiffing on Frankie Montas

Now that they’ve strengthened the outfield, an offseason mission for the New York Yankees is to add to their pitching rotation. After missing out on signing of Yoshinobu Yamamoto, the Yankees made an effort to re-sign Frankie Montas. Despite a disappointing injury-riddled time in New York, the Yankees were interested in bringing Montas back for another shot now that he’s healthy. Montas ultimately signed with the Cincinnati Reds. 

The Yankees are looking for someone to fit into their rotation along with Gerrit Cole, Carlos Rodon, Nestor Cortes, and Clarke Schmidt. Right now, they simply don’t have a fifth starter. They have some young depth, including Luis Gil (looking to bounce back after Tommy John surgery) and Yoendrys Gomez. Depth is always needed, as injuries arise, but they need a fifth starter.

Where do the Yankees look next? Top options remaining in free agency include lefties Blake Snell and Jordan Montgomery. If the Yankees don’t lock up a pitcher in free agency, they may need to pivot to the trade market.

Jordan Montgomery would strengthen the Yankees' pitching rotation

The Yankees need Jordan Montgomery. It’s ironic considering Brian Cashman didn’t see Montgomery as a fit for their playoff rotation in 2022, with Gerrit Cole, Luis Severino, Nestor Cortes, and Frankie Montas slated as their starters. Montgomery was traded to the St. Louis Cardinals in exchange for center fielder Harrison Bader. He helped the Cardinals make the 2022 playoffs. Montgomery was then traded to the Texas Rangers ahead of the 2023 MLB Trade Deadline. He contributed to their postseason run and World Series title.

Rumors of a reunion between the Yankees and the 31-year-old free agent have floated throughout the MLB offseason. MLB insider Jon Heyman revealed that the Yankees are interested in bringing Montgomery back. Would he be willing to return to New York after being cast off? Despite the snub, Montgomery has a background with the organization that drafted him back in 2014. He has previously indicated that there’s no bad blood between him and the Yankees.

Despite spending six seasons with the Yankees, Montgomery never had much of an opportunity to pitch in the postseason with the club. He didn’t pitch in the ALDS or ALCS as a rookie in 2017. He was injured in 2018 and was left off the postseason roster in 2019 with not enough time to show what he could do after returning from Tommy John surgery. Montgomery pitched in Game 4 of the 2020 ALDS. The Yankees were knocked out of the playoffs in a Wild Card game in 2021.

In his time since being traded by the Yankees, Montgomery has proven he’s a reliable starter who can contribute to a postseason run. He had a 3.20 ERA in the 2023 regular season. He was a valuable asset for the Rangers on their road to the World Series. Montgomery held a 2.90 ERA across six games and 31 innings pitched in the 2023 postseason.

Now that he’s had an opportunity to log postseason innings, Montgomery has shown he can handle the big moments. With the Yankees looking to flip the script after a disappointing 2023 season that ended with missing the playoffs, a reunion with a reliable starter who has improved his value in recent years is a sensible move. Unfortunately, with increased value, he’ll come at a high price. Are the Yankees willing to pay enough to outbid other suitors? With limited options, they can’t afford not to.

The Yankees need to pull the trigger and bring Montgomery back to New York to fill out the rotation. If he does return, and the Yankees make a run in the 2024 postseason, expect to see a now-seasoned veteran Montgomery on the mound in the Bronx in October.