Insider Ties Cubs to Projected $110 Million Free Agent: ‘Cannot Rule That Out’

Getty Chicago Cubs president Jed Hoyer has a strong pitching staff going into the 2024 season, but it can always be improved.

Even as the Chicago Cubs seem to be the likeliest destination for a reunion with premier free agent Cody Bellinger, there’s a chance they pull off a blockbuster signing for their pitching rotation as well.

MLB insider Jon Heyman recently named the Cubs as a potential destination for reigning World Series champion Jordan Montgomery, seeming to hint that Cubs pitcher Jameson Taillon might be able to sway the free agent.

“Monty to the Cubs, not going to rule it out,” Heyman said in a video for Bleacher Report Walk-Off. “Monty (is) very good friends with Jameson Taillon, who I happened to run into when I was in Chicago about a month ago, and I’m sure he’d love to have him on the Cubs. And again, cannot rule that out.”

Heyman noted that the other teams linked to Montgomery include the Boston Red Sox, San Francisco Giants and Los Angeles Angels. 

Whichever team ends up signing him is likely to strike a deal in the six-year, $110 million range, per Sportrac.

Do the Chicago Cubs Need a Nine-Figure Pitcher?

In 2023, the Cubs’ pitching staff performed in the middle of the pack, finishing with MLB’s 14th lowest ERA,19th most strikeouts and 12th lowest OPS.

Last season, the Cubs saw seven pitchers start at least 10 games, with Justin Steele emerging as a bonafide top-of-the-rotation starter with a 3.06 ERA, 16 wins and 176 strikeouts in 30 starts. Ten-year veteran Drew Smyly had the next-most wins at 11, then Marcus Stroman (who was signed by the New York Yankees after the season) with 10 and Taillon with eight.

In smaller sample sizes, 26-year-old Javier Assad and 24-year-old Jordan Wicks demonstrated significant promise as well. 

The rotation also projects to include Kyle Hendricks (3.74 ERA in 24 starts in 2023) and Shota Imanaga, a Japanese professional who signed a four-year, $53 million deal with the Cubs in January.

All told, a major pitching acquisition may not be the biggest need for the Cubs, and Bellinger still appears to be a more likely candidate for a big deal there than Montgomery.

“Bellinger (is) likely with the Cubs, or that’s the likeliest scenario,” Heyman noted. “That’s the most likely scenario of all the scenarios I think for Bellinger, is to end up with the Cubs.”

Jordan Montgomery Would Immediately Become the Chicago Cubs’ Ace for 2024

If the team does want to pad its rotation, Montgomery would likely ascend to its top. Pitching in 11 starts for the World Series champion Texas Rangers after a trade last season, he maintained a 2.79 ERA and racked up 58 strikeouts in 67.2 innings.

As Brett Taylor noted for Bleacher Nation, there’s reason to believe a deal to bring the southpaw to the Cubs makes sense for the team.

“The right deal on Montgomery not only improves the rotation, it would improve the bullpen and the depth, and it could be a valuable addition for multiple years,” he wrote. “Bonus consideration? Because he could not receive a qualifying offer, Montgomery does not cost draft pick compensation. We know the Cubs care a great deal about that.”