Cubs Free Agency

Cubs free agency: Would Jordan Montgomery union make sense?

NBC Universal, Inc.

The Chicago Cubs in all likelihood feel as though their team is set to take the field for the 2024 season, but could a remaining free agent help establish them as the surefire favorite in the National League Central?

The free agent in question is pitcher Jordan Montgomery, who still remains on the market with just over three weeks until the start of the 2024 season.

Montgomery went a combined 10-11 in the 2023 season with a 3.20 ERA in 32 starts. He slashed his ERA to 2.79 in 11 starts after being acquired by the World Series-champion Texas Rangers, and picked up a pair of huge wins against the Houston Astros in the American League Championship Series.

Even with that resume, Montgomery still remains on the market as the clock ticks on the start of the regular season, and there’s been ample speculation about what kind of deal he would accept.

For the Cubs, the only way a deal would likely make sense for Montgomery would be if it were a short-term deal, perhaps similar to the one they had given to Marcus Stroman when he inked a three-year pact with the club prior to the 2022 season.

A longer-term deal would likely be seen not only as a block on pitchers like Cade Horton and Ben Brown, but would also take the Cubs out of the mix if they decided to jump back into the free agent market next year for a pitcher like Shane Bieber or Max Fried.

As for the viability of the short-term deal, Montgomery is represented by agent Scott Boras, who also represents Cubs outfielder Cody Bellinger. The slugger recently accepted a three-year deal with the Cubs, with opt-outs after each of the first two seasons.

On the question of whether Montgomery would accept a deal of similar structure, MLB insider Jim Bowden had this to say in the Athletic in the last few days.

“From what I’m hearing in conversations with major-league sources, it doesn’t sound like Montgomery will accept a pillow contract like the one Bellinger signed,” he wrote.

If Montgomery were to take a short-term deal, Bowden also reported that it would likely be with a team like the Rangers, who have shown reluctance to agree to long-term deals as they try to defend their World Series crown.

MLB Network’s Jon Morosi argues that a short-term deal is indeed a possibility for both Montgomery and for fellow free agent Blake Snell, who is still looking for a home.

While Morosi mentioned the Angels and Red Sox as potential options for Montgomery, such a deal could be enticing for the Cubs as well, especially with the openness of the National League Central for the taking this season.

The Cubs do have their starting rotation largely set, but adding a pitcher like Montgomery would not only ease pressure on Jameson Taillon to have a bounceback season, but it would also help backstop Justin Steele in the rotation and would allow the Cubs to ensure that pitchers like Kyle Hendricks get adequate rest.

The deal would also ease pressure on Shota Imanaga as he adjusts to big-league hitting, giving the Cubs even more incentive to explore a union.

The issue again would be what to do with some of the team’s younger hurlers. Adding Montgomery would certainly box Javier Assad and Jordan Wicks out of the conversation as rotation options, and both have shown flashes of serious skill on the mound that could play well in a middle or back-end rotation role.

What’s more, the deal would also send the Cubs sailing over the luxury tax threshold for the 2024 season. Currently, the team has around $6 million to play with, according to Spotrac, and while going over the tax isn’t necessarily the end of the world in year one, the compounding penalties for future overages could cause the Cubs some issues if they want to take another foray into the free agent market next offseason.

Deals like Hendricks’ and Smyly’s would be coming off the books, as would retained salary on Trey Mancini, but it still would require some creativity for the Cubs to make a Montgomery deal work, no matter how intriguing it might be.

Click here to follow the Cubs Talk Podcast.

Contact Us