On November 25, Major League Baseball’s hot stove season is starting to heat up, and one player in demand is left-handed pitcher Jordan Montgomery. The Texas Rangers are keen on bringing him back, but they face competition from two familiar teams, the New York Yankees and the St. Louis Cardinals.
Montgomery, who spent the first six seasons of his MLB career with the Yankees, was traded to the Cardinals in 2022. The Yankees, along with numerous other clubs, are also interested in Japanese pitcher Yoshinobu Yamamoto.
While the Cardinals have bolstered their rotation with recent signings, including Lance Lynn and Kyle Gibson, they still lack a true ace. They were reportedly interested in Aaron Nola before he signed a long-term deal with the Phillies, and they are considered favorites to acquire right-hander Sonny Gray.
On November 15, it was revealed that Montgomery had a highly successful three-month stint with the Rangers during the previous season. He played a pivotal role in the team’s World Series triumph, pitching like an ace in critical postseason games. Despite becoming a free agent, there’s a chance he might return to the Rangers, and insiders believe it’s a good fit given his previous success with the team.
However, the Rangers’ rotation currently seems crowded with Max Scherzer, Nathan Eovaldi, Jon Gray, Dane Dunning, and Andrew Heaney set to return, with Jacob deGrom aiming to join later in the season after recovering from elbow surgery. Montgomery is expected to command a substantial contract, potentially exceeding $100 million, making his re-signing with the Rangers uncertain.
Nonetheless, the Rangers have shown interest in major free agents like Shohei Ohtani and Josh Hader, suggesting they might make a push to re-sign Montgomery.
On November 9, it was reported that while Montgomery won’t secure a $200 million contract in free agency, he could come close. The veteran starter is believed to prefer a return to the Rangers, Cardinals, or Yankees, three teams he has previously played for. Experts estimate his potential contract could be around $127 million.
On November 7, the Boston Red Sox, under new chief baseball officer Craig Breslow, expressed their interest in Montgomery. The Red Sox are prioritizing strengthening their rotation and have already engaged in discussions with Montgomery’s agent, Scott Boras.
Currently, the Red Sox have several pitchers penciled into their 2024 rotation, including Chris Sale, Brayan Bello, and Kutter Crawford, with other options like Nick Pivetta, Garrett Whitlock, and Tanner Houck. Montgomery’s consistent performance, including a 2.90 ERA in the postseason, makes him an appealing option for the Red Sox.
Notably, Montgomery isn’t subject to draft pick compensation, which could make him a more attractive choice for the Red Sox compared to other top free-agent pitchers. Having spent the early part of his career with the Yankees, he also brings familiarity with the AL East division, and he has a history of solid performances at Fenway Park.