Ex-Cardinals $22.5 Million Star Reportedly 'Bound To Intrigue' Red Sox This Winter

The St. Louis Cardinals will join several clubs this winter in looking for ways to improve their roster after missing the playoffs for a second straight year in 2024.

For a well-respected organization such as the Cardinals, missing the playoffs is foreign and unacceptable among the fanbase. Frustration has reached an all-time high and many are eager for change.

Another franchise with one of the most dedicated fan bases in baseball, that has missed the postseason for the last three years, could be in the market for a former Cardinals pitcher this winter as it looks to rejuvenate its lackluster pitching staff.

"The prospect of dealing away minimal resources for a hurler (Jordan Montgomery) who knows the American League East well and has posted stalwart production in multiple places is bound to intrigue Boston (Red Sox) brass," ClutchPoint's Alex House wrote Wednesday when discussing possible landing spots for the former Cardinals pitcher this offseason.

Montgomery, who spent two years in St. Louis, has a $22.5 million conditional player option for 2025 with the Arizona Diamondbacks, which he hasn't officially picked up yet.

However, Diamondbacks owner Ken Kendrick's recent negative comments regarding Montgomery's poor performance in 2024 have created a sticky situation for the left-handed pitcher.

The soon-to-be 32-year-old could return to a club that doesn't want him or seek free agency. The odds of Montgomery neglecting to pick up his player option are slim to none, considering he posted an 8-7 record with a 6.23 ERA, 83-to-44 strikeout-to-walk ratio, .312 batting average against and a 1.65 WHIP in 117 innings pitched for Arizona this season.

The 2023 World Series champion's market value will plummet if he elects free agency, so collecting the $22.5 million from the Diamondbacks would be wise. He could stick it out with Arizona for a year or perhaps be traded this offseason as Kendrick looks to remove Montgomery from the payroll.

Boston wanted Montgomery before he signed with Arizona but his agent at the time, Scott Boras, made it impossible for both parties to reach a deal. The feeling was mutual for the southpaw, so a Red Sox-Diamondbacks trade could be a transaction that makes everyone happy.

Considering how poorly Montgomery performed this season, Boston likely wouldn't have to give up much of anything to land him. If the Red Sox are serious about improving their rotation for 2025, they should be ready to take a chance on the veteran hurler, who still has plenty left in the tank.