Cubs Linked to ‘Perfect’ Free Agent Projected for $110 Million Deal

Jed Hoyer

Getty Chicago Cubs President Jed Hoyer seems willing to spend on a "win-now" 2024 season.

The Chicago Cubs have demonstrated a willingness to spend big to improve their playoff chances in the immediate future, signing Cody Bellinger to an $80 million deal and Shota Imanaga to a $53 million one.

But their offseason spending might not be over yet, with an anonymous MLB competitor telling the New York Post’s Jon Heyman that the Cubs are an ideal match for free-agent southpaw Jordan Montgomery, who is projected to earn a six-year, $110 million contract, per Sportrac.

“Monty would be perfect for the Cubs,” the source said. “They can afford him.”

Heyman added that, even after signing Bellinger, the Cubs “still look like barely the cream of a middling NL Central,” suggesting the team could use another significant acquisition to make the most of their recent investments.

Jordan Montgomery Could Lead the Chicago Cubs Rotation

Even after the team lost Marcus Stroman to the New York Yankees in free agency, starting pitching does not currently project to be a major weakness for the team. The rotation is set to be led by Justin Steele and Imanaga, making it relatively strong at the top.

“I suspect some teams are going to kick themselves that the Cubs got Imanaga this cheaply,” Dan Szymborki wrote for FanGraphs, with the site’s ZiPS model projecting a close race in the division. “ZiPS is projecting a skosh of regression from Justine Steele, but some of that is simply the realities of projecting pitchers; both Imanaga and Steele fall just outside of the top 10 in NL starter projections, but with inning counts that are a little behind the league’s elite.”

Montgomery, however, would likely surge to the top of that order, particularly where inning counts are concerned.

In seven big-league seasons, Montgomery has maintained a 3.68 ERA and netted 140 total starts. In 2023, he pitched for a 3.20 ERA for the St. Louis Cardinals and the Texas Rangers, which he ultimately led to a World Series Championship. He is seen as a relatively durable workhorse, with at least 157 innings pitched in each of the last three seasons.

What Kind of Deal Will Jordan Montgomery Sign?

But even with an anonymous competitor telling Heyman that the Cubs “can” afford Montgomery, the projected cost of signing him seems to be why he’s still on the free agent market well into Spring Training. 

“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 gave Marcus Stroman when he inked a three-year pact with the club prior to the 2022 season,” James Neveau explained for NBC Sports Chicago. “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 Montgomery’s willingness to accept less than the $110 million market value that’s been projected, there are mixed reports. Jim Bowden of The Athletic reported that “it doesn’t sound like” he’d accept a “pillow contract” similar to Bellinger’s. 

But Bob Nightengale of USA Today suggested both Montgomery and fellow premier free agent Blake Snell would be open to such a compromise.

“They are now willing to exchange long-term deals for flexible, short-term contracts, if necessary, just as Bellinger and (Matt) Chapman did,” Nightengale reported.

If Montgomery is listening on shorter-term offers, the Cubs would likely see significant competition to add him.

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