Pitchers and catchers have already started reporting to spring training, but top starter Jordan Montgomery still remains unsigned — for now. On January 8, MLB.com’s Mark Feinsand predicted the left-hander would be the next of agent Scott Boras’s available clients to sign with a team this offseason, going as far as to project he’d join a team “by next week.”
Montgomery has already stayed on the free agency market longer than expected, so a deal in the coming days wouldn’t be surprising. Still, it’s hard to identify a clear frontrunner to sign the 31-year-old, with both the Texas Rangers and Boston Red Sox in the mix for his services.
While Feinsand wrote that Montgomery “seems destined for a reunion with the Rangers if the two sides can agree on a number,” insider Jon Morosi was less ready to count the Red Sox out as contenders to sign him.
“The Rangers are the favorites to sign [Montgomery], but I wonder if the Red Sox could make a late push by clearing salary with a Kenley Jansen trade,” Morosi wrote.
The Red Sox have been linked to Montgomery all winter, especially since the pitcher recently moved to Boston. Montgomery’s wife, McKenzie Dirr, is completing a residency at a hospital in the city, and this offseason, Montgomery has been working out at Boston College. Despite this potentially giving the Red Sox an inside edge to sign him, nothing has been made official.
Montgomery’s market has been hot all winter, and with a large number of other free agent pitchers now signed to teams, he’s unquestionably one of the top starters still available. In 2023, Montgomery made 32 regular-season starts between the St. Louis Cardinals and Rangers, posting a 3.20 ERA, 1.19 WHIP, and 166 strikeouts. He made six appearances (five starts) in the Rangers’ ultimately successful playoff campaign, recording an ERA of 2.90 and 17 strikeouts.
Montgomery’s Projected Contract Value
Regardless of which team Montgomery ends up signing with, he’s certainly not going to come cheap.
On November 6, 2023, Tim Dierkes, Anthony Franco, and Steve Adams of MLB Trade Rumors projected Montgomery would be looking at a six-year, $150 million deal this winter, and on November 9, ESPN’s Kiley McDaniel predicted the pitcher would land a five-year, $106 million contract. These predictions put Montgomery’s AAV in the range of $21-25 million.
Rangers vs. Red Sox
Montgomery just helped the Rangers win their first World Series title in franchise history, so the team knows how successful they can be with him on their roster. The Rangers only acquired the starter at the trade deadline and he was undeniably crucial to their playoff success, but this season, Montgomery could potentially play an even more important role.
Texas starters Jacob deGrom and Max Scherzer are both on the IL to start the season, and it’s uncertain if they’ll be back on the mound in 2024 at all. The Rangers recently signed Tyler Mahle, but he’s also expected to be on the IL after undergoing Tommy John surgery last year. If the Rangers want to contend in 2024, they need an ace to carry their starting rotation until at least one of their injured starters gets back, and Montgomery has already proven how effective he can be for them.
The Red Sox also need starting pitching, and Montgomery would walk straight into the top of their rotation. In 2023, Boston’s starting rotation posted an underwhelming 4.68 ERA to rank 22nd in MLB, and with newcomer Lucas Giolito replacing ace Chris Sale, things could be even more dire in 2024.
Still, Montgomery’s contract value is likely to be a major deterrent for the Red Sox, and it could be the biggest reason a deal between the two parties doesn’t work out. The Rangers are famously open to spending big to get top players, so they are less likely to be held back by the cost.
Regardless of which team Montgomery favors, now it’s just up to Boras to close the deal.