Is Jordan Montgomery Still a Possibility for the Cubs? Should He Be? Yankees Back in?

Jordan Montgomery pitches for the Texas Rangers.
Jordan Montgomery pitches for the Texas Rangers.

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Will Jordan Montgomery end up on the Cubs? The short answer is probably not. I’m not trying to hide the ball there. The Cubs have already announced their starting rotation, and it’s not exactly thin. Even with Jameson Taillon starting the season on the shelf, the Cubs rotation is five deep (Justin Steele, Kyle Hendricks, Shota Imanaga, Jordan Wicks, Javier Assad), and that’s ahead of Drew Smyly, Hayden Wesneski, Cade Horton, and Ben Brown.

I don’t think that’s the best staff in baseball by any means, but it’s a solid group with plenty of depth, including both steady veterans and high-upside prospects. I’m perfectly fine with the Cubs starting pitching this year, as is.

But Jordan Montgomery Does Fit, Right?

But let’s also be honest here: Jordan Montgomery would immediately slot in as AT LEAST the second most trusted starter in that group. And for as much as I like all of the pitchers listed above, it’s not difficult to poke holes in the Cubs staff.

  • Kyle Hendricks is 34-years-old, and expecting him to repeat his 2023 season is not a safe assumption.
  • Jameson Taillon had a horrendous first-half last year and is currently injured.
  • Shota Imanaga looks like a stud, but has never thrown a pitch in the big leagues.
  • Jordan Wicks and Javier Assad had a lot of success in the rotation last year, but neither has the track record or the “stuff” to match Montgomery’s potential upside. And Assad has a lot of value in the ‘pen and as a swing-man.
  • Drew Smyly and Hayden Wesneski have flashed success in the big league rotation, but both looked far better in relief last year: Wesneski (5.51 ERA as a starter, 3.57 ERA as a reliever), Smyly (5.62 ERA as a starter, 2.51 ERA as a reliever).
  • Cade Horton and Ben Brown are great prospects, excellent even, but counting on either of them for anything is bad process.

Throw in the fact that the Cubs are *this close* to being the actual on-paper favorite in the NL Central and, well, yeah. Maybe signing Montgomery isn’t a “need,” but he would absolutely be a nice-to-have.

So What’s Stopping Them?

But here’s the thing, even if you think Montgomery’s lack of a deal this close to the season โ€” and what that means for the sort of deal he’ll get – makes him more likely for the Cubs (a fair conclusion), he’s not the only recent free agent who fit that description. I could have made that same case for 3B Matt Chapman, starter Blake Snell, and DH J.D. Martinez, each of whom would have filled a theoretical position of need for the 2024 Cubs. But all three signed with other teams over the last two weeks to the exact sort of last-minute, short-term deal the Cubs would’ve needed to get something done. Maybe that tells us something about their intentions.

So should we expect it to be any different for Jordan Montgomery? I’m not so sure.

Jordan Montgomery Rangers
Kim Klement Neitzel-USA TODAY Sports

Cubs Content for Now?

But the conversation did come up at The Athletic this morning, so I thought it was worth considering one more time (bolded emphasis mine):

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 couldnโ€™t have been what Montgomery envisioned after he helped the Texas Rangers win last yearโ€™s World Series. Free agency hasnโ€™t gone as planned for Montgomery, a Scott Boras client who remains unsigned into March Madness.

Instead of sensing an opportunity, sources indicated the Cubs seem content to let things play out before making their next big moves at the trade deadline. At the start of camp, Cubs chairman Tom Ricketts described the luxury-tax threshold as โ€œa natural place for us.โ€ Cubs president of baseball operations Jed Hoyer then closed a deal with Boras to retain Cody Bellinger, taking a $30 million chunk out of this yearโ€™s payroll.

So he still makes sense for the Cubs, but “sources indicate” that the Cubs are not itching to get anything done.

Context and Reaction

According to Roster Resource, the Cubs current payroll for purposes of the luxury tax calculation is right there at almost exactly $237M, which is the first threshold of the 2024 luxury tax. So signing Jordan Montgomery, even on a bargain, would all but guarantee that they’d go over the tax, probably even if they were to sell off at the trade deadline. And right or wrong (I’d argue wrong), the Cubs don’t want to be locked into that outcome.

Let me rephrase that: I think the Cubs will be perfectly happy to go over the tax *at the deadline* if they’re competing. But I also think that they REALLY want the flexibility to get back under if they’re not. It’s a little cowardly, if you ask me. But that’s how I understand their thinking.

But wait, there’s more.

Latest Jordan Montgomery Rumor

According to Jon Heyman, after finding out that they’ll be without Gerrit Cole for much of the season, and whiffing on their preferred target, Blake Snell, the Yankees have gotten back in contact with Jordan Montgomery. Montgomery has already pitched for the Yankees, so there’s familiarity there. And they reportedly had big money on the table for Snell throughout the offseason – so money is available.

So if Montgomery is still seeking that big-money, long-term deal, the Yankees might be his only option (and, of course, Montgomery is the YANKEES’ only high-quality option, too). It actually makes a good amount of sense for both sides if you stop there.

But here’s the thing: if Montgomery is going to sign before the season begins (an important detail, but hold that thought), he might STILL be looking for big money, even more than the Yankees were willing to give their preferred target, Blake Snell: “Montgomeryโ€™s camp compares him to Aaron Nola, who got $172 million over seven years,” writes Heyman not so inconspicuously.

And since the Yankees CBT (luxury tax) payroll has already exceeded the fourth and highest tier for 2024, any deal they sign now will be subject to the 110% luxury tax. That’s a BIG premium to pay to add Montgomery this late in the game, even for the Yankees. And if they gave him a long-term deal, they might be locking themselves into that tier for years to come. And remember, there are also significant penalties in the draft and international free agency for being that far over that many years in a row.

Short-Term Deal and Timeline Implications

But what if Jordan Montgomery wants to go short term, like the rest of the Scott Boras clients who whiffed this winter, looking to get back out there for his bigger deal next offseason? Well if he does, then he’s better off waiting until after Opening Day* to sign, so that no team can extend him a qualifying offer attaching him to draft pick compensation next winter. In other words, if he signed a short-term deal within the next six days, he might actually be in a worse position next year than he is now (a year older and attached to draft pick compensation … and that’s the best case scenario, because he could still get hurt or underperform).

I bring *that* part up because if you are holding out hope that the Cubs will get involved – maybe those sources cited by The Athletic were trying to drum up leverage for the Cubs – it’ll necessarily have to be on a short-term deal. And if it’s going to be a short-term deal, Montgomery won’t be signing that before Thursday.

*Did “Opening Day,” for the purposes of the CBA already happen when the Dodgers played the Padres in the Seoul Series? I don’t think that counts, but it’s an open question for me.

Too-long, Didn’t Read:

Okay, whew. This was a lot of details, so let me boil down the conclusions here just for some closing brevity.

  • The Cubs staff and depth is fine as is, but Jordan Montgomery would clearly be an upgrade.
  • However, the Cubs didn’t jump at similar opportunities to sign short-term deals with Matt Chapman, Blake Snell, or J.D. Martinez.
  • The Cubs are reportedly still a fit for Montgomery, but The Athletic’s sources indicate that they’re content to stand pat until at least the trade deadline.
  • We believe the above is true, because the Cubs are already at the luxury tax limit and prefer to have the flexibility to get back under at the deadline if things go sideways.
  • After whiffing on Snell and losing Cole, the Yankees have re-engaged Montgomery, but Montgomery might still be seeking a $170M+ deal.
  • The Yankees might be reluctant to sign such a deal given their current luxury tax status (110% penalty plus IFA and draft implications).
  • If Montgomery is going to sign a short-term deal, it won’t be until after Opening Day, so that he cannot be extended a qualifying offer.

Any questions?

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Tab Bamford
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Feb 06, 2025
Chicago Blackhawks Kyle Davidson

NHL Insider Talks Blackhawks Trade Buzz, Rantanen Trade Fallout, Future Contract Strategy

On Thursday morning, Elliotte Friedman dropped a loaded written version of his "32 Thoughts" and there are some good Blackhawks-centric nuggets in there. Here's what got my attention: Blackhawks trade buzz I noted in my bullets this morning that there were 14 teams represented in the press box scouting the Blackhawks-Oilers game. Friedman notes a light schedule and the looming two-week break meant there was plenty of attention in Chicago...

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Michael Cerami began covering the Chicago Cubs for Bleacher Nation as a part-time contributor in 2015. One year later, he joined Bleacher Nation full-time, covering the Chicago Cubs and Major League Baseball. Today, Michael runs Bleacher Nation, contributing as a writer (Cubs, MLB) and an editor for all sections of the site, including the Chicago Bears, Bulls, and Blackhawks, as well as MLB, NBA, NHL, and NFL. In 2019, Michael was the co-host of NBC Sports Chicago's Cubs Post-Game Show Outside the Ivy. You can find him on Twitter/X @Michael_Cerami

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The Catchers Part of Pitchers and Catchers, Morning Arrivals, and Other Cubs Bullets

Super Bowl prediction: nachos and ice cream and stiff-arming kids that demand my attention. Spring Training officially begins today, with Cubs pitchers and catchers reporting to Mesa, Arizona. Of course, the majority of them have been in Mesa working already...

THE BIG DAY IS HERE! (No, Not That One)

You wait for months and months for this days. When, after so much patience and build up, the happiest day of the year arrives. When it finally happens. CHICAGO CUBS PITCHERS AND CATCHERS REPORT TO SPRING TRAINING TODAY!!! ... what,...

What the Cubs Can Still Do, More Old Friends Sign, Spring Training Visuals, and Other Cubs Bullets

Everybody else was doing it, so I thought I would go ahead and get sick. As a treat. Pitchers and catchers officially report tomorrow, marking the nominal beginning of Spring Training. The Cubs' roster may or may not be complete...

Chicago Cubs Announce Non-Roster Invites to 2025 Spring Training

As expected, the Chicago Cubs today announced their non-roster invites to big league Spring Training. The full list is below, with the reminder that these are the NON-40-MAN players who are coming to big league camp. So if you're wondering...

Obsessive Alex Bregman Watch: Cubs Remain Involved, But Level-Setting Harder to Say

There's not a whole lot doing yet today on the Alex Bregman front, but there are a few updates to share, at least. First, from Bruce Levine, who says the Cubs are still working at it and seems to imply...

What About Lefty Jalen Beeks As an Additional Depth Option for the Cubs?

The Athletic did a thing where they picked an available free a gent for each of the 30 MLB teams, and although I want to underscore that there's no "rumor" here, I did find the selection for the Cubs to...

The Many New Top Chicago Cubs Prospects Lists

The many, many pre-2025 Chicago Cubs top-X-number-of-prospects lists have dropped the last couple weeks - MLB Pipeline is the only major one we're still waiting on - and if you haven't seen all or any of them, I thought I'd...

Shaw and 2B-3B, Ricketts on McCaskey, Early Start, Mizuhara, Padres, and Other Cubs Bullets

I feel like a genius and an idiot: for *YEARS* I have loved peanut butter sauce as an ice cream topping, but you can't get it everywhere, and there's basically no good take-home variety. So I get it when I...

Obsessive Alex Bregman Watch: How Many Suitors? How Many Years? Red Sox Back-Up Plan? More

A few Alex Bregman bits to chew on as you settle down for the night ... Jon Heyman tonight writes that although Bregman is receiving "creative short-term offers," he and Scott Boras are still looking for six+ years. That tracks...

Free Agent 3B Yoan Moncada Signs with the Angels

The Chicago Cubs, ostensibly still in the market for a free-agent third baseman, will watch one option fall off the board tonight. Former White Sox third baseman - and offseason Cubs target - Yoan Moncada is reportedly signing a modest...

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Sonego vs. Van de Zandschulp Prediction at the Open 13 Provence – Monday, February 10

On Monday, Lorenzo Sonego (No. 34 in the world) faces Botic Van de Zandschulp (No. 84) in the Round of 32 at the Open 13 Provence.In this match against Van de Zandschulp (+110), Sonego is the favorite with -140 odds.Open...

Virtanen vs. Korda Prediction at the Open 13 Provence – Monday, February 10

Otto Virtanen (No. 97 ranking) will meet Sebastian Korda (No. 22) in the Round of 32 of the Open 13 Provence on Monday, February 10.In this matchup, Korda is the favorite (-275) against Virtanen (+210) .Open 13 Provence InfoTournament: The...

Nishikori vs. McDonald Prediction at the Delray Beach Open by VITACOST.com – Monday, February 10

Mackenzie McDonald (No. 125) will take on Kei Nishikori (No. 71) in the Round of 32 at the Delray Beach Open by VITACOST.com on Monday, February 10.In this matchup, Nishikori is the favorite (-220) against McDonald (+170) .Delray Beach Open...

Collignon vs. Medjedovic Prediction at the Open 13 Provence – Monday, February 10

In the Round of 32 at the Open 13 Provence on Monday, Hamad Medjedovic (ranked No. 95) takes on Raphael Collignon (No. 124).Medjedovic is getting -295 odds to beat Collignon (+220).Open 13 Provence InfoTournament: The Open 13 ProvenceRound: Round of...

Nardi vs. Altmaier Prediction at the Open 13 Provence – Tuesday, February 11

No. 77-ranked Luca Nardi will face No. 93 Daniel Altmaier in the Open 13 Provence Round of 32 on Tuesday, February 11.Nardi carries -115 odds to beat Altmaier (-110).Open 13 Provence InfoTournament: The Open 13 ProvenceRound: Round of 32Date: Tuesday,...

Zhang vs. Halys Prediction at the Open 13 Provence – Tuesday, February 11

In a match scheduled for Tuesday, Quentin Halys (No. 74 in rankings) will meet Zhizhen Zhang (No. 50) in the Round of 32 at the Open 13 Provence.Zhang is the favorite (-115) in this matchup, compared to the underdog Halys,...

Yunchaokete vs. Hijikata Prediction at the Delray Beach Open by VITACOST.com – Monday, February 10

Rinky Hijikata (No. 73) will meet Bu Yunchaokete (No. 68) in the Round of 32 at the Delray Beach Open by VITACOST.com on Monday, February 10.In this matchup, Yunchaokete is the favorite (-135) against Hijikata (+105) .Delray Beach Open by...

Open 13 Provence Schedule Tuesday, February 11: Matchups & TV/Live Stream Info

The slate at the Open 13 Provence on February 11 includes five matches, among them Zhizhen Zhang (ranked No. 50) against Quentin Halys (No. 74). For live coverage of matches, and highlights, tune into Center Court and Center Court Live...

WTA Doha, Qatar Schedule Tuesday, February 11: Matchups & TV/Live Stream Info

The slate at the WTA Doha, Qatar on February 11 includes three matches, including Coco Gauff (ranked No. 3) versus Marta Kostyuk (No. 22). For live coverage of matches, and highlights, tune into Center Court and Center Court Live on...

Bublik vs. Gasquet Prediction at the Open 13 Provence – Tuesday, February 11

In the Open 13 Provence Round of 32 on Tuesday, we have a matchup featuring No. 130-ranked Richard Gasquet against No. 49 Alexander Bublik.With -140 odds, Bublik is favored over Gasquet (+110) in this match.Open 13 Provence InfoTournament: The Open...

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