The veteran lefty, coming off a disastrous season with the Diamondbacks, could be a buy-low trade candidate for the Birds.
It’s no secret that the Orioles need starting pitching, but in a slow-developing market, they’ve yet to make an addition this offseason. Blake Snell, who would have been a nice fit for the Orioles, signed a five-year, $182 million deal with the Dodgers. The biggest names in free agency, Corbin Burnes and Max Fried, may take their time looking for a blockbuster offer.
It remains to be seen whether the notoriously prudent O’s front office is willing to shell out the money it will take for a top-of-the-line pitcher, even under new owner David Rubenstein. In the meantime, though, they should be pursuing every opportunity to upgrade the rotation, even if that means taking on another team’s salary dump to acquire a back-end type of starter. And veteran southpaw Jordan Montgomery may just fit that bill.
If the Orioles are interested in Montgomery, the Diamondbacks are, shall we say, a motivated seller. At $25 million, the well-traveled lefty was an expensive dud in his first year with Arizona in 2024, finishing the season with a disastrous 6.23 ERA in 117 innings and ultimately getting banished to the bullpen. After the season, Diamondbacks president Ken Kendrick openly regretted the Montgomery signing, calling it “a horrible decision to invest that money in a guy who performed as poorly as he did. It’s our biggest mistake this season from a talent standpoint.”
To think that just one year ago at this time, Montgomery was on top of the world. He was a prize free agent who’d just propelled the Texas Rangers to a championship, pitching brilliantly down the stretch and in the playoffs after they acquired him from St. Louis in July. Montgomery was as reliable as pitchers come, compiling a three-season stretch in which he had a 3.48 ERA in nearly 100 starts, including 2.79 during his remarkable Rangers run. At 30 years old, he expected a contract that would set him up comfortably for nearly the rest of his career.
It didn’t play out that way at all. Montgomery, then represented by Scott Boras, had a very similar experience to fellow Boras client Blake Snell, waiting all winter for a nine-year deal, only to be left twisting in the wind and still unsigned well into spring training. It wasn’t until March 28 — Opening Day — that Montgomery settled for a one-year deal with the D’Backs with a vesting option for 2025. Shortly afterward, Montgomery fired Boras as his agent, saying he “kind of butchered” his contract negotiations.
The lack of spring training threw Montgomery into a tailspin, just as it did for Snell, who signed with the Giants on March 19 and got off to a miserable start. But while Snell recovered in the second half and returned to his former glory, Montgomery never did. He only got worse as the season went on, looking nothing like the poised hurler who’d beaten the Diamondbacks in the World Series the previous year. The last time his ERA was under 5.00 was on May 25, his seventh start of the season. His final start of May was an eight-run, 10-hit disaster. So was his final start of June.
Across the board, Montgomery’s numbers were way off from his career norms. His WHIP was 1.65, up significantly from his 1.21 career mark beforehand. He averaged more than three extra hits and nearly one extra walk per nine innings than before. His strikeout rate plummeted to a career-worst 6.4, ranking in the fourth percentile in MLB. His K/BB mark, which was a respectable 3.41 entering the season, dropped to 1.89.
Of particular concern was a dip in velocity, as Montgomery’s sinker and four-seam fastball both were 1-2 mph slower than the year before. All told, he was one of the least valuable players in baseball with a -1.4 WAR. The Diamondbacks, who missed the playoffs by just one game, surely can’t help wondering how their season would have played out if they hadn’t bothered signing Montgomery.
Montgomery smartly exercised his $22.5 million player option with Arizona for 2025 rather than head back to free agency with his value at an all-time low. The Diamondbacks could hang onto him and hope he’ll improve with the benefit of a full spring training, but the comments from the team president Kendrick indicate the team is looking to part ways with the veteran.
That’s where the Orioles come in. The O’s could acquire Montgomery for a negligible return that wouldn’t involve any significant prospects, especially if they agree to take on most or all of his salary. It’s an interesting, low-risk proposition with a potentially rewarding payoff.
Montgomery still has the attributes that would have made him an intriguing free agent target for the Orioles a year ago. He’s a dependable veteran with a track record of success, including ample AL East experience as a member of the Yankees from 2017-2022. If the O’s could be sure that’s the version of Montgomery they’d be getting, he’d be a fine addition. The question, of course, is how much stock they should put into his nightmarish 2024. Were his struggles merely a one-year blip, compounded by his late start to the season? Or has he fallen off a cliff at age 31?
That assessment will need to be made by smarter people than myself, and the Orioles have many. I trust that the front office and pitching coaches would have some ideas about how to fix whatever’s ailing Montgomery, though of course there’s no guarantee they’d be successful (see Rogers, Trevor). Still, there’s not much downside in giving it a try. The cost isn’t prohibitive, and if he can pitch well enough just to be a fourth or fifth starter who keeps his team in the game, there’s value in that. He’s no Snell or Fried, and he wouldn’t replace Burnes as the club’s ace, but Montgomery can help the Orioles in his own way.