A's Off-Season Trade Target: Jordan Montgomery

It looks like the A's are looking to add to their 2025 team payroll. Could this former World Series Champion be a possible option for the team?

Sep 22, 2024; Milwaukee, Wisconsin, USA; Arizona Diamondbacks starting pitcher Jordan Montgomery (52) pitches in the first inning against the Milwaukee Brewers at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images / Benny Sieu-Imagn Images

The off-season is filled with players shuffling from one team to the next, and many players are on the move throughout the league. The A’s have made several moves including the addition of 2-time All-Star Luis Severino, Jeffrey Springs, and Gio Urshela. 

It has been reported that the A’s need to get their payroll up over $105 million for the 2025 season to avoid risking grievance from the MLBPA. Adding Severino to a 3-year $67M deal certainly helps the team get closer to their targeted payroll, but more moves need to be made. 

The A’s ended up trading for left-hander Jeffrey Springs which added an additional $10.5 million to the 2025 team payroll, and Urshela added $2.15 million as well. That puts their total luxury tax payroll estimate at around $90 million.

The moves won’t stop here though. The team will likely have to add more money to their current payroll. After addressing needs at third base and the top of the rotation, the A’s will have a choice on what other position they’d like to improve. 

When looking at the A’s 40-man roster, the A’s currently have 7 left-handed pitchers. This includes Ken Waldichuk, who will likely miss most of the 2025 season. It also includes long shots to make the Opening Day Roster such as Brady Basso, Hogan Harris, and Jacob Lopez. This leaves T.J. McFarland as the lone lefty bullpen arm, with JP Sears and Jeffrey Springs as lefty rotation options for the club.

With that being said, the A’s have a clear need for a left-handed pitcher. One possible option for the A’s to spend some money and fill this hole is MLB veteran and former World Series champion, Jordan Montgomery.

In Montgomery’s lengthy eight-year career, he has posted a 4.03 ERA. If you take out his 2019-2020 seasons where he only pitched a combined 12 games, and his 2024 campaign, he never had a season ERA over 3.88. His ceiling is certainly higher than some of the team's other rotation options, which could be worth the risk for the A’s. 

On paper, his 2024 season with the Arizona Diamondbacks looked super rough. He posted a 6.23 ERA in 117 innings. One big reason that could have caused a down year for Montgomery, is that he did not sign until late March, missing Spring Training with the D-backs.

The late signing was caused by his former agent Scott Boras holding out many of his players that off-season in hopes to get more money--which didn’t turn out well for his clients. Jordan Montgomery ended up firing Boras after his signing with the Diamondbacks. He received a two-year, $47.5 million deal with an opt-out. After his struggles, he decided to stick with the D-Backs and is owed $22.5 million in 2025.

Jordan Montgomery is certainly a guy who could be a bounce back candidate in 2025. Although, it seems as if the Diamondbacks would likely be willing to trade him, and also willing to trade a prospect alongside him to get rid of his large contract.

The Diamondbacks also recently added top free agent arm, Corbin Burnes. Arizona is unlikely to keep Montgomery’s contract with the addition of Burnes, so there’s a high chance they trade him, and the A's should be in line to acquire the southpaw.

If the A’s were to swing a trade to acquire Jordan Montgomery, they’d likely get a prospect alongside him, though it's not likely that it would be a top-end guy. The A's could also request that Arizona eats some of Montgomery's salary for 2025, along with potentially taking on the low salary of someone like Seth Brown, who is set to make $2.7 million next year as a platoon outfielder. Brown's departure would open up playing time for either Esteury Ruiz or potentially prospect Colby Thomas in left.

If the A's went this route, they could keep their own payroll fairly close to the needed $105 million, and the Diamondbacks could shed some payroll of their own while getting a useful lefty bat.

Out of all the options the A’s have with the remaining salaries that they will have to dish out this off-season, the team should consider adding Jordan Montgomery to an improving A’s pitching staff. A top three of Severino, Springs, and Montgomery would be formidable in the winnable AL West.