Main Photo Credits: Matt Kartozian-USA TODAY Sports

Despite their staff being set for the 2024 season, there could be another fit in the Cubs rotation in the free-agent market. Left-handed pitcher Jordan Montgomery remains unsigned with the MLB’s official regular season starting today in South Korea. 

Montgomery is another Scott Boras client who has elected to hold out to get the compensation he feels is fair. He has seen fellow Boras counterparts sign contracts during Spring Training. Cody Bellinger, Matt Chapman, and Blake Snell all inked deals. They were much less money than initially expected entering the offseason. All three signed two or three-year contracts that include opt-outs after this season, essentially putting them back on the market next offseason. 

Montgomery likely won’t net a deal longer than any other Boras client who has held out this long. However, his market is rather interesting. The Boston Red Sox have come up frequently in rumors, along with a potential return to the Texas Rangers. Outside of that, specific team names haven’t been tossed out there as much as in Blake Snell’s saga. 

One of His Best Seasons to Date

After getting traded from St. Louis to Texas at the trade deadline, Montgomery flipped a switch. In 11 regular season starts, Montgomery went 4-2 with a 2.79 ERA. Across 67.2 innings tossed, the southpaw registered a 1.09 WHIP. 

Montgomery was essential to the Rangers’ World Series run this past fall. His work in the ALCS against Houston proved just that. Montgomery allowed just two runs in 14.0 innings pitched in three total appearances, good for a 1.29 ERA in the series. Although his lone World Series start didn’t bounce his way, the Rangers wouldn’t have been there in the first place if it wasn’t for the Sumter, SC native. 

Winning Pedigree 

Winning a title with Texas last year is enough of a winning background for Montgomery’s resume. Lone Star state aside, his experience with successful organizations has lasted his entire career. 

The now 31-year-old began his Major League journey with the Yankees in 2017, possessing an under-four era in six seasons. He was shipped off to St. Louis in a swap for outfielder Harrison Bader in 2022. 

As much as Cub fans don’t want to applaud the Cardinals in any way, they are another organization that has succeeded in how they run things. Despite never winning a title in New York, there is a standard for that club that echoes excellence at all times in everything performed. It helps the Cubs and other franchises that could be after Montgomery, knowing that he has won at multiple stops in the show. He knows what that culture and general expectations look like daily. 

Many Cubs fans believe Montgomery would be an excellent addition to the team’s rotation in 2024. The only worry comes with the rotation in place right now. Along with youngster Jordan Wicks, Justin Steele and Shota Imanaga are already in the fold. Would four lefties be too many for this staff? Only time will tell if that situation happens, but front-of-the-line starters like Montgomery are a luxury to have in any shape or form. The fit in the Cubs’ rotation could very well be there if Montgomery joins his fourth franchise. 

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