There is a simple reason that free-agent lefty Jordan Montgomery has been connected with the Cubs so often. It’s because the signing would just make so much baseball sense. The North Siders have a chance this season to seize the N.L. Central, especially as one of the other favorites in the division, the Reds, have undergone a wave of injuries. The Central crown and a spot in the postseason is there for the taking.
But pitching depth is one of the questions that could hold back the Cubs this year, and Montgomery would so easily answer that question. A successful Cubs run in 2024 will require Justin Steele to repeat his breakout 2023 season. It would require that injured No. 2 man Jameson Taillon get healthy quickly. It requires that Shota Imanaga build on his spring momentum and hold up for an entire season.
Oh, and it requires the Cubs to fashion a decent back end of the rotation with Jordan Wicks and Javier Assad getting the first crack at the 4-5 spots.
Montgomery is, essentially, insurance against the Cubs coming up short on any of those requirements. That’s why, as The Athletic’s Patrick Mooney wrote this week, Montgomery “still makes sense” for the Cubs.
Cubs ‘Still Make Sense’ for Major Signing
Mooney also quoted team president Jed Hoyer saying, “We’re still having conversations,” as the team prepares to leave Arizona, which surely perked up some ears in Chicago. But then Hoyer also said the roster is not likely to change.
And he also said, according to MLB.com, that signing older pitchers (Montgomery is 31) to expensive deals (Spotrac projects his market value at six years and $110 million) is not tenable.
“It’s hard to rely on the free-agent market for enough pitching. It’s really expensive and it’s usually older [players]. Hopefully, we have some young arms that can help us,” Hoyer said.
Still, the point from Mooney is a valid one: “An entire offseason and almost all of spring training flew by and Jordan Montgomery still makes sense for the Chicago Cubs in theory.
“This waiting game couldn’t have been what Montgomery envisioned after he helped the Texas Rangers win last year’s World Series. Free agency hasn’t gone as planned for Montgomery, a Scott Boras client who remains unsigned into March Madness.”
Jordan Montgomery Deal Would Be a Taxing Issue
It is a two-way problem, though. Montgomery is still asking too much money for the Cubs, or for anyone else, to bite on signing him. Several others teams, including the Red Sox, Yankees and Astros, have been linked to Montgomery, too, as well as his old team, the Rangers. But Texas opted to tab another late-signing free agent, former Phillies pitcher Michael Lorenzen, instead.
If Hoyer decided he wanted Montgomery on the staff, there would be an even bigger hurdle to clear—the luxury tax. Owner Tom Ricketts has shown no willingness to allow the team over the $237 million tax threshold. According to Spotrac, the Cubs are at $230 million in projected payroll, just under the tax.
Even if Montgomery took a significant discount for this year, it would likely send the Cubs above the tax line. That is, of course, a Ricketts problem and not a problem for the team and its fans. But Ricketts signs the checks, and he has said the team is comfortable operating right around the tax threshold.
Signing Montgomery would change that quickly. It makes sense. But it remains highly unlikely.
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Cubs Again Linked to Projected $110 Million Starter Who ‘Still Makes Sense’