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.