Can I Sell You on Jordan Montgomery as the Final Piece for the Cubs' Rotation?

[Matthew Trueblood]

If ever a player needed a change of scenery, and if ever there was a time to ignore the ugly numbers, this might be it.

Image courtesy of © Ron Chenoy-Imagn Images

The modern baseball analytosphere demands that we have a good damn explanation for why any player who was bad in Year X should be any good in Year X+1. We have all kinds of numbers, all kinds of angles, all kinds of ways to see and to say whether or not a player was good in a given season, and if they weren't, then we expect there to be a concrete, performance-centric, highly data-fied reason why we should believe they'll turn things around. If there isn't one, any argument in support of that player will be met with skepticism—if not outright disdain.

Well, admittedly, I don't have an ideal analytics-based argument for the possibility that Jordan Montgomery will turn things around after his woeful 2024. There are some such arguments, and I'll briefly deliver them, but I want to start by putting my best case forward, and I don't think the best case for a Montgomery rebound is rooted in the numbers. I also don't think the truth of his terrible campaign with Arizona last year lives in them.

Scott Boras laid an egg when it came to Montgomery's free agency. He was a highly sought-after free agent last winter, but Boras priced his client out of the range of interested teams, until freezer burn overtook him so badly that he ended up signing a highly dissatisfactory deal on Opening Day. The season was a disaster, and it included several discouraging trends. Montgomery lost about 1.5 miles per hour on both of his fastballs, on average—some of which can be put down to his overlong free agency interfering with any organic ramp-up for the regular season.

The Diamondbacks also asked Montgomery to make some changes that were ill-suited to his unique skill set and approach, including swapping his cutter for a slider; leaning more on his four-seamer and less on his sinker; and locating differently. As a result, Montgomery lost the strike zone somewhat, especially because he doesn't throw strikes with his four-seamer as reliably as with the sinker. Using the former more and the latter less was an error, in his case, and while it could theoretically have worked and then-pitching coach Brent Strom has a track record of success with that pitch as the backbone of pitchers' arsenals, there was neither the time nor the trust between player and organization that usually comes when someone signs as a high-profile free agent. They didn't get a spring training together, and Montgomery was never happy enough in his place there to be especially open to whatever good suggestions the team did make.

Montgomery was genuinely bad in 2024, and there's no one reason to believe he'll be better in 2025, other than the simple, human, psychological one: as long as he's traded sometime this month and can get acclimated to the idea of a new team, then enjoy a normal spring training, he should enter the season as a much, much more prepared, mentally healthy pitcher. Last winter, I thought he was a marvelous fit for the Cubs, and I still think he will be. I think he'll bounce back resoundingly from the frustration and disappointment of 2024. I wouldn't be surprised if he gets that tick on the fastball back and goes right back to being the southpaw workhorse, playoff hero, and mid-rotation fixture he was when he hit the market last year.

Plenty of teams would have given him a six-figure deal, if his agent hadn't demanded such a gaudy one until the last possible moment (and beyond). Now, though, Montgomery is available on a one-year deal, which the Diamondbacks would have to subsidize in order to move him. That could mean eating some of the money he's owed, or it could mean sending along a prospect to clear as much cash as possible. Either way, the Cubs would benefit by acquiring him not only because I think he'll bounce back, but because they would have such leverage in a negotiation with Diamondbacks head honcho Mike Hazen.

Do the Cubs desperately need Montgomery? No. But he's the type of player who, because of the circumstances of this offseason, should cost far less to acquire than he's really worth, and he'd give the rotation the upside it's lacking right now—along with a healthy dose of stability. Landing him would also free up one or two of the Cubs' young pitchers to be dealt for a high-end trade asset, should that opportunity arise.

Many teams and pundits are feeling smug about Montgomery after last season, because they feel vindicated for not having believed in him. I think that's exactly the wrong conclusion. Montgomery wasn't stranded on the market because he was secretly bad, in some way that didn't show up while he was racking up 360 innings pitched over the previous two years and dominating in the playoffs as the Rangers made a run to the World Series. He was bad in 2024 because he'd been so disruptively stranded on the market. As such, he's a good buy-low opportunity at this moment, and if the Cubs have grand plans for 2025, they should prepare themselves to pounce.

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[CubinNY]

no sale.

[Development DL]

I love forward , and creative  value thinking .  Interesting at the very least .  Kicking the tires would be prudent . 

[Bertz]

I'm torn on Montgomery, and admittedly haven't thought about him since Rea.  On the one hand, he seems like one of the most obvious bounce-back candidates in the league.  The number of guys who have signed late, ate crap for a season, and then resumed their careers like. nothing happened is fairly lengthy.  And with Montgomery especially, it's easy to draw a line from abbreviated spring training -> not at 100% physically -> velo drop -> poor performance.  If Montgomery is throwing 93+ a few starts into the season it's pretty easy to say he's back.

On the other hand, particularly after Rea I don't know that I want to burn yet more roster spots on projects.  If Ben Brown or Cade Horton are striking out 35% of the batters they're facing at Iowa, and all of the Cubs' back end veteran types are pitching adequately, how many bullets do we have to sit around watching get wasted in Des Moine?

Ultimately I guess I'd chalk it up to cost.  If AZ eats enough salary that Jed can acquire Montgomery without having to skimp on the bench and bullpen options he wants, I'm probably up for it.  If Montgomery though is the difference between Kirby Yates + Mark Canha vs. Paul Sewald + Conor Joe I'm going to have a fit.

[Matthew Trueblood]

38 minutes ago, Bertz said:

I'm torn on Montgomery, and admittedly haven't thought about him since Rea.  On the one hand, he seems like one of the most obvious bounce-back candidates in the league.  The number of guys who have signed late, ate crap for a season, and then resumed their careers like. nothing happened is fairly lengthy.  And with Montgomery especially, it's easy to draw a line from abbreviated spring training -> not at 100% physically -> velo drop -> poor performance.  If Montgomery is throwing 93+ a few starts into the season it's pretty easy to say he's back.

On the other hand, particularly after Rea I don't know that I want to burn yet more roster spots on projects.  If Ben Brown or Cade Horton are striking out 35% of the batters they're facing at Iowa, and all of the Cubs' back end veteran types are pitching adequately, how many bullets do we have to sit around watching get wasted in Des Moine?

Ultimately I guess I'd chalk it up to cost.  If AZ eats enough salary that Jed can acquire Montgomery without having to skimp on the bench and bullpen options he wants, I'm probably up for it.  If Montgomery though is the difference between Kirby Yates + Mark Canha vs. Paul Sewald + Conor Joe I'm going to have a fit.

Well put. And yeah, you'd like to think they'll make sure they have a true top-flight reliever secured before considering an addition like this. (BTW, though, I'm not sure I wouldn't take Joe instead of Canha. It's close.)

[SOFNR]

59 minutes ago, Bertz said:

I'm torn on Montgomery, and admittedly haven't thought about him since Rea.  On the one hand, he seems like one of the most obvious bounce-back candidates in the league.  The number of guys who have signed late, ate crap for a season, and then resumed their careers like. nothing happened is fairly lengthy.  And with Montgomery especially, it's easy to draw a line from abbreviated spring training -> not at 100% physically -> velo drop -> poor performance.  If Montgomery is throwing 93+ a few starts into the season it's pretty easy to say he's back.

On the other hand, particularly after Rea I don't know that I want to burn yet more roster spots on projects.  If Ben Brown or Cade Horton are striking out 35% of the batters they're facing at Iowa, and all of the Cubs' back end veteran types are pitching adequately, how many bullets do we have to sit around watching get wasted in Des Moine?

Ultimately I guess I'd chalk it up to cost.  If AZ eats enough salary that Jed can acquire Montgomery without having to skimp on the bench and bullpen options he wants, I'm probably up for it.  If Montgomery though is the difference between Kirby Yates + Mark Canha vs. Paul Sewald + Conor Joe I'm going to have a fit.

Yah, Montgomery has always been pretty low on my list. If we are grabbing a pitcher in the 23-25 mil range I'd much rather go for Flaherty, Castillo, Lopez. I'd probably even prefer going with Wicks or Assad over giving that sort of money to Montgomery given their payroll limitations. Now after the Rea/Thielbar signings it's looking pretty difficult to pay 20+ for a SP while still adding to the back end of the bullpen and the bench. If Montgomery was only going to cost you 13-15 maybe it's worth exploring. Although I'm also not willing to give up anything of much significance to take a shot at him bouncing back.

[Rcal10]

1 hour ago, SOFNR said:

Yah, Montgomery has always been pretty low on my list. If we are grabbing a pitcher in the 23-25 mil range I'd much rather go for Flaherty, Castillo, Lopez. I'd probably even prefer going with Wicks or Assad over giving that sort of money to Montgomery given their payroll limitations. Now after the Rea/Thielbar signings it's looking pretty difficult to pay 20+ for a SP while still adding to the back end of the bullpen and the bench. If Montgomery was only going to cost you 13-15 maybe it's worth exploring. Although I'm also not willing to give up anything of much significance to take a shot at him bouncing back.

I think the only way they consider Montgomery is if Az takes on some of his salary. So he wouldn’t be $23M. Maybe $16m or so. At $16M if they can still add Yates and a decent bench bat, I would consider him. He also can’t cost much in the way of a prospect. The trade would have to be a payroll dump. Then I wouldn’t mind him. He would cost the Cubs less than Lopez or Castillo in a trade, and for 1 year I would take him at $16M with Yates and a good bench bat over Flaherty for $24M and Paul Seward and a lesser bench bat. I do think he can absolutely be as good as Castillo or Flaherty next years.

[Rob Grothman]

On 1/1/2025 at 12:43 PM, Brock Beauchamp said:

Welcome to NSBB!

If the Cubs bring in Monty for over 20 million, it defeats purpose of giving Bellinger away for nothing?

I am sure Monty recovers a bit from last year's decline. However, since Cubs are acting like small market team(including 3rd highest tickets in league?), there has to be better ways to spend that money.

Not much Hoyer does makes sense. Even bringing in Tucker, one of my favorite guys in league, who is bound to get plenty of long term contract offers, will not get one from Cubs because they have a policy of not giving out long term contracts. So you give up Cam Smith, Mr. 1032 OPS on his way to double A in just 32 games. Thinking we might have paid too much for Mr. Tucker for a year's rental or more likely at trade deadline. Hoyer is desperate and still not making sense.

[Brock Beauchamp]

1 minute ago, Rob Grothman said:

If the Cubs bring in Monty for over 20 million, it defeats purpose of giving Bellinger away for nothing?

I am sure Monty recovers a bit from last year's decline. However, since Cubs are acting like small market team(including 3rd highest tickets in league?), there has to be better ways to spend that money.

Not much Hoyer does makes sense. Even bringing in Tucker, one of my favorite guys in league, who is bound to get plenty of long term contract offers, will not get one from Cubs because they have a policy of not giving out long term contracts. So you give up Cam Smith, Mr. 1032 OPS on his way to double A in just 32 games. Thinking we might have paid too much for Mr. Tucker for a year's rental or more likely at trade deadline. Hoyer is desperate and still not making sense.

There's a lot to be confused about, for sure. If the Cubs swap Bellinger for Montgomery, I think that's an improvement. I actually consider that smart flexibility on the part of Hoyer.

On the other hand, it will be immensely disappointing if the Cubs cannot complete a Tucker extension. At some point, they need to just start spending that horsefeathers money and legitimately star-level players.

[Rob Grothman]

22 hours ago, Matthew Trueblood said:

Well put. And yeah, you'd like to think they'll make sure they have a true top-flight reliever secured before considering an addition like this. (BTW, though, I'm not sure I wouldn't take Joe instead of Canha. It's close.)

While I agree cubs bring in vetran closer to add support. I do not believe it will be a 12 million type. More like 6 for Yates for a season or maybe Sewald because Hodge is the closer. This way you make Hodge beat out Yates or have two closers. So a lefty closer would be nice?