Jordan Montgomery Finally Has a Job
Some 49 hours before their first regular season game, the Arizona Diamondbacks brought up the house lights to end the 2023-24 Hot Stove League. Jordan Montgomery is headed west on a one-year contract with a vesting option.
The 31-year-old Montgomery had been a well-regarded high-volume starter, but the 2023 postseason brought him to the verge of stardom. The Texas Rangers traded for Montgomery at the deadline, and with Jacob deGrom and Max Scherzer battling injuries, it was the big South Carolinian who emerged as the team’s ace. He won three games in the postseason, including Game 7 of the ALCS in a multi-inning relief appearance on two days’ rest, and was one of the World Series champion’s breakout stars.
That championship, of course, came at the expense of Arizona, his new team. The Diamondbacks, having come so close to winning it all, had already brought in reinforcements by trading for third baseman Eugenio Suárez and signing outfielder Joc Pederson and lefty starter Eduardo Rodriguez. Last October, this was a team with an improvised rotation; with Montgomery, Rodriguez (once he returns from his season-opening IL stint), Zac Gallen, Merrill Kelly, a full year of a maturing Brandon Pfaadt, and a healthy Tommy Henry, it’s among the best in the sport.
Montgomery will also be reunited with his college teammate, first baseman Christian Walker. The two played for a College World Series title together in 2012, though Montgomery was too young to be a member of the 2010 Gamecocks team that beat Kelly’s Arizona State Sun Devils in Omaha. Suffice it to say, this signing is bubbling with narrative portent.
Montgomery will make $25 million in 2024, and if he pitches anything resembling a normal workload, he’ll have an equivalent player option for 2025. If Montgomery makes 10 starts, that player option will pay out at $20 million, with an additional $2.5 million to be earned at both 18 and 23 starts, bringing the maximum value of the contract to $50 million over two years.
Montgomery’s one-plus-one deal gives his agent, Scott Boras, a hat trick of his prized clients asking for a mulligan on their free agency experience. Blake Snell took a one-year deal with an option to sign with the Giants; Snell’s new teammate Matt Chapman has a contract that could stretch as long as four seasons, but from which he can opt out after one. By holding out and trying to play the market aggressively, Boras managed to land all three of his prize clients with contracts Ted from Scrubs could’ve negotiated.
It’s a humbling defeat for the most powerful agent in American sports, especially as he gears up for next offseason, in which he’ll try to make Juan Soto the highest-paid player in baseball history.
The timing of Montgomery’s signing is interesting as well; unlike Snell and Chapman, Montgomery was not saddled with a qualifying offer this past offseason. By virtue of not having been with the Rangers all year, he was ineligible to be extended one. Because a player can only receive one qualifying offer in his career, Snell and Chapman will be in the clear the next time they become free agents. Montgomery, theoretically, could still be tagged.
If Arizona activates Montgomery for Opening Day, the Diamondbacks could stick a qualifying offer on him after this season. But Nick Piecoro of the Arizona Republic cited a source saying that Montgomery will start the season on a minor league assignment so he can get into game shape. That would count as not spending the entire season on the major league roster, leaving Montgomery free to leave without receiving a qualifying offer.
Montgomery might have burnished his reputation with that stellar showing last October — though he’s been excellent in the playoffs in lower-visibility roles, dating back to his days as an amateur — but he would’ve been an incredibly valuable addition for Arizona even before that.
Since 2020, he is 20th in pitcher WAR; the fact that he’s one spot behind deGrom on that leaderboard raises obvious questions about whether that makes him a capital-A Ace on a per-inning basis. (Montgomery has thrown more than twice as many innings as deGrom over the past four seasons.) But pitchers who can throw Montgomery’s volume are rare now, and they’ll only become more so in the coming years.
Montgomery has started 104 games over the past four seasons, which is the ninth-highest total in baseball. Only 19 pitchers have started 100 or more. That list includes two pitchers who are currently rehabbing torn UCLs (Lucas Giolito and Sandy Alcantara), two others who’ll start the season on the IL (Gerrit Cole and Taijuan Walker), the 40-year-old Charlie Morton, and three pitchers who aren’t good enough to trust in a playoff rotation (Kyle Gibson, Jordan Lyles, and Patrick Corbin).
That leaves Montgomery in a group of 11. Eight of those (Dylan Cease, Aaron Nola, Kevin Gausman, Luis Castillo, Logan Webb, Corbin Burnes, Zack Wheeler, and Gallen) are either Cy Young winners or make frequent appearances on Cy Young voting ballots. The other two, apart from Montgomery, are Chris Bassitt and José Berríos: no. 2 or no. 3 starters who’d upgrade almost any rotation in baseball.
So if the question is whether Montgomery is more like a Nola or Webb, or if he’s more like a Bassitt (and perhaps I’m being uncharitable to Bassitt or overly charitable to some of the pitchers in the first group), a one-year, $25 million contract is an absolute steal in either case.
And somehow, the Diamondbacks have been able to add all this veteran help to their pennant-winning team, splash $25 million on an opportunistic signing during Holy Week, and still have almost $22 million to go before they hit the lowest competitive balance tax threshold.
Earlier this week, I wrote about the subtle difference between using structural leverage to sign good players to team-friendly deals, versus just locking up whoever’s around because they’re cheap. In terms of actual 2024 salary, Montgomery is now Arizona’s highest-paid player, obviously. But Madison Bumgarner is tied for second place.
The Diamondbacks have limited their pre-free agency extensions to their stars: Corbin Carroll and Ketel Marte. Marte won’t make more than $16.6 million in any year of his contract, and Carroll won’t hit that number until 2029; both are massively overperforming their deals. And after taking a bath on Bumgarner, GM Mike Hazen has skillfully navigated the most treacherous type of baseball transaction: The mid-tier free agent signing. So many GMs have gotten fired by overspending on replaceable players, but Hazen has limited Arizona’s outlays to shorter-term deals at reasonable salaries, all while targeting solid contributors.
Finally, the Diamondbacks have taken the money they’ve saved and reinvested it in the roster. They weren’t in on the biggest free agents — Shohei Ohtani, Yoshinobu Yamamoto, Nola — but when the Mariners were willing to give Suárez away to anyone who’d pay his salary, Hazen was there. And when Montgomery entered the final week of March without a contract, Hazen had cash in hand and was able to point to a roster that should get back to the playoffs.
The Diamondbacks have their fair share of problems organizationally, but most of them are above the baseball ops level. With the major league team, the D-backs have got a good thing going, which allowed them to attract Montgomery and make it even better.
Michael is a writer at FanGraphs. Previously, he was a staff writer at The Ringer and D1Baseball, and his work has appeared at Grantland, Baseball Prospectus, The Atlantic, ESPN.com, and various ill-remembered Phillies blogs. Follow him on Twitter, if you must, @MichaelBaumann.
Maybe Arizona will sign Joey Pankake to an advisor role to complete the Holy Triumvirate of Gamecock Legends.
Montgomery’s 180 IP with a 4 ERA might be more valuable on the Diamondbacks than on a team with a deep bullpen but it might not. I’m not sure. Maybe Blake Snell fits better on the Phillies. Or Jacob DeGrom on the Dodgers. It’s not obvious to me.
The only times in his career Montgomery has had a 4+ ERA are the shortened 2020 season and when he only pitched 4 IP in 2019.
I always thought Boras was making a mistake by carrying Bellinger/Chapman so far into the offseason, but am surprised Snell/Montgomery got burned so badly too. Boras has historically won more than he lost, but I think the days of giving him the benefit of the doubt are over after this offseason.
The entire market is down. Focusing on just Boras misses the bigger picture.
The middle and lower tier Free Agents have been squeezed across the board. The J.D. Davis arbitration fiasco is a canary in the coalmine.
The players have bigger problems than the hyped Boras 4 storyline.
Is it, though?
There were 27 players whose median Fangraphs crowd projection was for $20M+.
Excluding the Boras big 4 (Bellinger, Snell, Montgomery, Chapman) and yet-unsigned Clevinger, 22 players were estimated for $1.34B total (across 67 seasons).
They signed for $1.36B total (across 64 seasons) after adjusting Ohtani’s contract to $460M due to deferrals.
Note that this is not including Yamamoto and Jung-Hoo Lee who signed a much more lucrative contract than expected.
Meanwhile the Boras quartet was expected to sign for $454M (20 seasons) and only guaranteed themselves $221M (9 seasons).
This is not the first time Boras messed up (Keuchel, Moustakas, Maldonado, etc.), and his winter wasn’t a complete failure as he also represented Jung-Hoo Lee. But this is the first time when Boras messed up four of his biggest clients in a single offseason. I would not read too much into it (Boras is capable of updating his strategy just as MLB teams dealing with him are), but blaming the overall market is not consistent with the fact that overall, non-Boras free agents did largely as expected.
It’s not about big FAs vs mid FAs like you say, but it’s not about Boras either. Lots of non-Boras guys have gotten much worse contracts than comparable players as well this offseason (ie Lorenzen, Clevinger, Rosario, Taylor).
It’s about there being a bimodal market, where teams like the Phillies, Dodgers, Padres, and like 10 other teams having money to spend boosts markets, and once those teams run out of cap space the market crashes b/c it’s just the cheap bum teams in the bidding.
The obvious relationship is that the FA market crashed once the big players spent all their money and it was down to the mid-market teams. Agents probably expected that mid-market contenders like Orioles would still have some FA interest/activity to keep markets up but a ton of teams just don’t seem to care.
It’s also obviously not the Bally stuff. The Royals gave Michael Wacha $32mil/2yrs earlier in the offseason. Teoscar Hernandez got $23.5mil. Sonny Gray got $75mil/3yrs.
These guys just ran out of buyers even though plenty of teams should still have money to spend.
I feel like part of it may be that teams and the market don’t consider these guys top of the line players worthy of paying a premium, and owners don’t either, so one of Boras’ strategies doesn’t work. Lots of the players I can pinpoint as people I feel like didn’t do well with Boras were at the top of the market that year but not truly worth top of the market money. Who knows whether the mistake was Boras telling them they could get more or the player saying “I’m the best FA pitcher on the market, I deserve $175M”.
all of this to say: if you’re a true top of the line guy, Boras still seems like he gets you your money. If you’re not clear top tier FA headliner in any year, he may either not work as well for you or you may have to accept more volatility to take a shot at that truly giant contract. I’m sure team spending comes into play too, but I think that there is some type of player that Boras may not be as tailored to.
Yeah, the bigger is issue is that those guys were merely star players who were trying to get paid like superstars.
While it only takes one team to overpay the perceived market value, none of those guys managed to get such a bite this time.
The Bellinger situation seems like it could work out. He had rebounded from a terrible run and his batted ball data looked iffy. I would have just taken a longer deal now but the market wasn’t that strong. The deal he got gives him a lot of flexibility and he won’t have the QO next year.
I think it’s pretty clear that this backfired on Chapman, Snell, and Montgomery. Chapman’s extension offer from the Blue Jays seems like the high water mark for him, and it’s going to be hard for Snell or Montgomery to have a better platform year.
We know that Snell could have walked out of there with $150M and I feel pretty confident Montgomery could have gotten $120M. Are they going to get back to that next offseason? Maybe but it’s unnecessarily risky.
Agree, I think Boras kinda got lucky with Bellinger and had the Cubs bidding against themselves. But Snell and Montgomery taking 2yr deals with an opt out is a huge fail. It’s fair for position players to bet on themselves but every pitcher is only a throw away from major surgery. There are basically no Nolan Ryan’s or Greg Maddux’s anymore. Pitchers need to max out dollars and years in free agency.
Agree with this. In another thread I said that there’s no such thing as a pillow contract for a pitcher. Especially pitchers on the wrong side of 30, which most free agent pitchers of import are. There’s “long term” and there’s “not long term”.
I was going to say that Zack Greinke is like Nolan Ryan and Greg Maddux but then I saw that he’s 85th on the all-time innings list. Then Justin Verlander 92nd and Max Scherzer 166th.
I cannot believe this was the best offer Montgomery got this offseason. We know Snell’s contract wasn’t the best offer he got. Boras did his clients a disservice by holding out for unrealistic numbers.
I’m surprised Boston didn’t offer him something like this, esp with the reports about his wife working in the area. I get wanting to actually be on a competitive team/not wanting to take a pillow contract in the AL East meat grinder, but still. Baltimore? Seems like a good fit. Yankees didn’t want to be charged double but they need the pitching floor that Montgomery provides.
If Boston is building for the next 3 years or something, a longer term deal would have made sense. The question becomes is Montgomery going to become a $150m 2 Win pitcher.
Rumor is that Montgomery had multiple $100M offers on the table, but Boras was demanding either a big $160M+ deal like Nola or an opt-out deal like Sonny Gray/Correa, where its shorter but all the risk goes on the team.
Sonny Gray didn’t get any opt-outs. He got a straight three-year deal with a mutual option for a 4th year.
It is absolutely shameful that the Red Sox are going to be rolling out their paper-thin rotation when Montgomery was available on this deal. And his wife lives in Boston.
I don’t know if it would universally be considered a benefit among ballplayers to work in the same city as their wives, given a choice.
The most interesting thing about this deal is that nearly everyone except for the D-Backs is going to get told they screwed it up. Boras and Montgomery obviously screwed it up; there is no way he should have exited this offseason with less than $120M guaranteed.
The Red Sox and Yankees got connected to him when they desperately needed pitching but they blew their money on (checks notes) Marcus Stroman and Lucas Giolito. Them, along with probably another dozen teams should have beaten this deal by 50% or more and could really use a playoff-worthy starter. This is definitely a situation where other teams fans should be mad.
Meanwhile, the D-Backs suddenly have one of the top rotations in Major League Baseball with a solid 1-5, and it’s not going to hurt the balance books long term at all. The NL West is loaded.
The Red Sox didn’t “blow their money” on Giolito – they had plenty of money to sign both.
At least Stroman is a groundball pitcher. Gumby was a fly baller who I saw get BABIP’d and then rocked too many times as a Yankee.
So what are the D-backs’ organizational problems?
Yeah that second to last line really has me scratching my head too. No idea what he is referring to. Arizona seems to have an average-ish or better front office and owner (relative to others).
How’s the farm? TV contract? Loge sales? Season ticket sales?
There’s more to organizational strength than the quality of the FO and the pockets of the owner.
The front office is elite, and as long as Kendrick stays out of their way it shows. But Kendrick has a habit of occasionally mandating things, which predictably goes poorly.
Hazen and crew don’t get nearly enough credit for the job they have done.
This for one:
https://www.cbssports.com/mlb/news/diamondbacks-dont-rule-out-moving-without-public-funding-for-renovations-we-may-run-out-of-time-in-phoenix/
I agree that owners asking for subsidies is crappy but is it really unique? They all want handouts for stadiums.
Bad ownership; good front office given constraints
So, the dodgers overpaid for Yamamoto by just a bit, huh?
I don’t think you can say that based on this contracts. If Yamamoto is an ace that contract is fair for a 25 year old (and one lousy start is not enough for us to say he isn’t an ace). Montogomery should have been in line for a 9-figure deal, seems pretty obvious Boras just butchered the negotiations.
Look, there’s no way the dodgers could have known this was how the offseason would play out. And Yamamoto may live up to the contract. But given that Snell and Montgomery signed for less than $100m guaranteed, I don’t think there’s a good argument that the Dodgers didn’t overpay relative to the market.
Snell and Montgomery’s free agencies are not representative of the general market. When compared to every other major pitching signing (Nola, ERod, Imanaga), and the 6/$150M contract the Yankees allegedly offered Snell, Yamamoto’s contract scales appropriately imo, provided that you believe in his ace level projection.
There was nothing stopping the Dodgers from signing Snell and Montgomery in addition to Yamamoto if they wanted to. James Paxton is in their rotation. They need a SS and have a bunch of young pitchers. They chose not to do that.
I think that contract is absolutely insane. It may turn out to be a fair deal, because who knows. But it’s insane.
That depends entirely on how well he does. If he’s good it’s a good deal. If he sucks it’s a bad deal. The amount of money 50% higher or lower wouldn’t change that.
Of course different amounts of money change whether it’s a good deal or not.
It will be interesting to see if any of his players change agents.
Two questions that Boras clients should ask themselves: “Does he have too much like-kind product to me?” That’s a question both Snell and Montgomery had to ask. And, next time around, do I accept the slightly light extension or early bid for good money/years or hope to do better. Past is not necessarily prologue, but If you are looking for some of the biggest money/CBT penalty types, there’s only so far they can go, and getting good money up front might be the only money they are going to spend.
At the very least they needed to do a better job of finding teams below their historic spending levels and with competitive ambitions. After the Yankees offered Snell $150M, Boras should have had some idea of who was in a position to top that before saying no
And after getting Semien they were unlikely to be an option anymore.
Other teams figured it out and adjusted.
Likewise, when tbe Dodgers made tbeir moves, they were off the board.
As more and more teams made their choices, Snell and Montgomery should have realized their market (and big deal prspects) were fading.
At least Bellinger settled for a decent multiyear deal that allows him a down year before going back out, on his terms.
Snell and Montgomery don’t have that option. They *have* to shine this year or they’re stuck with a 2 year deal and little chance of a long deal afterwards.
Good point. I think what happened to Boras is that he thought the supply of money was unlimited, not realize teams set their own limits, The CBT penalty thresholds are a huge bargaining win for the Owners. They don’t spread the penalty over the whole roster, they think cost of addition only
Won’t Montgomery be eligible for a QO after this season if he opts out? Seems like he should have waited two days to sign this deal. Maybe that’s part of the allure for the D-backs, but I doubt it.
Nope.
He would be if he was rostered on opening day but word is he’ll be in the minors as his spring training until he builds up to the usual outing.
No word if it is his idra to avoid the QO.
Interesting. I didn’t know that wrinkle about the QO regarding being in the minors.
“as he gears up for next offseason, in which he’ll try to make Juan Soto the highest-paid player in baseball history.”
Let me ask you a question: are you on drugs?
Soto is a bat-only player with zero complementary skills who is a bad defender and baserunner. He’s nowhere near the levels of real superstars like Ohtani and Trout in terms of performance. Really, he’s not even half the player Ohtani is.
Soto’s young age? Nah, that doesn’t really matter much when you are already a slow, unathletic bat-only player.
In other words, Soto is just a DH masquerading as an OF.
Everybody knows he’s really a DH, and a non-Ohtani DH at that, who is not the most talented and marketable player in baseball history.
Soto is probably the most overrated player in baseball right now.
Compare Soto’s career with Trout’s through 25, and Trout’s worst full season is better than Soto’s best full season in terms of both WAR and wRC+.
Compare Soto with Yordan Alvarez, who is a year older. You can see that Alvarez is a better hiitter/baserunner/fielder than Soto.
I guess I am a pitcher availability nihilist, or enough of one, where if I am offered Snell or Montgomery for comparable contracts, I take Snell every day of the week and twice on Sundays. But this is fine…
Different breeds.
Snell has a higher performance ceiling but is fragile, Montgomery more of a solid two but more reliable.
Seems to be that teams are just getting wise to the fact that guaranteeing these long-term deals is insane. We could have a whole other thread about which deals actually were net positive vs which ones weren’t. I know for me, I can rattle off many more bad ones than good ones. The Strasburg one by itself is the stuff of nightmares.
Eh, both Snell and Montgomery had 4-5 year offers, the problem is that they were demanding 7-10 year deals.
What was Boston’s standing offer to Montgomery is going to be the “why didn’t Malcolm Butler play a single snap in the Super Bowl” for the next few years. Just a huge miss not to elevate a team with low-80’s win projection into contention. FSG really is treating the team like a lifeless private equity asset to be stripped for parts.