Top Landing Spots for Free Agent Jordan Montgomery

Jordan Montgomery hits free agency as one of the best left-handed starters on the market. Where could he sign?

ST PETERSBURG, FLORIDA - OCTOBER 04: Jordan Montgomery #52 of the Texas Rangers celebrates a strikeout during Game One of the Wild Card Series against the Tampa Bay Rays at Tropicana Field on October 03, 2023 in St. Petersburg, Florida. (Photo by Bailey Orr/Texas Rangers/Getty Images)

As the 2023-24 MLB offseason marches on, Jordan Montgomery finds himself as one of the top available starting pitchers on the market.

Montgomery, 30, is the definition of a “late bloomer”. The fourth-round pick in the 2014 draft did not make his big league debut until 2017 and wasn’t able to consistently make 30 starts a year until 2021 at the age of 28.

Now, however, he sits alongside Blake Snell as one of the top left-handers to watch during the offseason.

After a strong showing in each of the 2021 and ’22 campaigns, expectations were high for Montgomery entering this past year. Traded at the deadline from the Cardinals to the eventual champion Rangers, “Monty” was solid as a rock for a team marching towards its first-ever World Series victory.

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In 11 starts for the Rangers, Montgomery went 4-2 with a 2.79 ERA and 160 ERA+. Then, he put up a seven-inning shutout performance over the Rays in the Wild Card Series, and he was an integral part of the Rangers’ deep postseason run. Overall, he tossed 31 innings in this year’s postseason with a sparkling 2.90 ERA.

At the end of the day, Montgomery finished the 2023 campaign in the 82nd percentile in walk percentage. In addition, he finished in the 93rd percentile in Pitching Run Value, per Baseball Savant.

Nearly all 30 teams around the league have a need for starting pitching. Let’s take a closer look and identify the top five fits for Montgomery in free agency.

Arizona Diamondbacks

As things currently stand, Zac Gallen and Merrill Kelly will be the only arms with much experience in Arizona’s rotation. Beyond them, Brandon Pfaadt, Ryne Nelson and Tommy Henry figure to round out the group, but there’s an obvious need for some additional innings.

Montgomery would provide the 2023 NL Champs with a steady veteran presence, which is exactly what they need if they hope to go back-to-back.

This past season, the Diamondbacks had the tenth-highest ERA amongst starting pitchers at 4.67; their 4.36 FIP ranked 15th. Again, there’s a need for at least one more arm, and Montgomery would fit that bill nicely.

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Boston Red Sox

The Diamondbacks had the tenth-highest starter ERA and the Red Sox were one spot lower with the ninth-highest (4.68). With a new GM in town, the Red Sox figure to be active on both the trade and free agent markets.

Nick Pivetta and Brayan Bello are the only true locks for Boston’s 2024 rotation. Chris Sale has already been tabbed as the club’s Opening Day starter, but who knows what kind of health issues he’ll run into this offseason. Over the past few years, the 34-year-old has seemingly been made of glass.

Adding Montgomery to the rotation would add some much-needed depth to the starting five. If the Red Sox are serious about a swift return to contention, this would be a good place to start.

Cincinnati Reds

The Reds are a team that has not been talked about enough this offseason. After a third-place finish in the NL Central, the club appears to be in prime position to move up in the standings in the coming years. With the Brewers on the brink of a potential sell-off, Cincinnati could leapfrog Milwaukee as soon as next year.

In 2023, Reds starters posted a combined 5.43 ERA. Only the Rockies’ and Athletics’ pitching staffs were worse than that.

Hunter Greene, Andrew Abbott, Graham Ashcraft, Brandon Williamson and Nick Lodolo are all full of potential but are also five largely unproven twentysomethings. A veteran presence like Montgomery would immediately give Cincinnati some legitimacy in their quest to regain the Central.

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Los Angeles Dodgers

Outside of free agent Clayton Kershaw and rookie standout Bobby Miller, the Dodgers received little to no production from their starters in 2023. If Kershaw does not re-sign this winter, the team’s need for more starting will be amplified ten times over.

Julio Urías ran into some off-the-field issues that could take him out of action for the foreseeable future. Michael Grove and Emmet Sheehan each showed occasional glimpses of promise but largely struggled.

Noah Syndergaard, acquired last winter, was flipped at the trade deadline. Meanwhile, Lance Lynn, who was acquired at the deadline, recently signed with the Cardinals. Simply put, there are a whole lot of innings that need to be filled on the Dodgers’ staff.

Montgomery and his strong postseason track record would be a great fit in Los Angeles, and the Dodgers easily have the funds to lure him in.

New York Yankees

Another club that should have no issues writing Montgomery a check, the Yankees have already been “looking at” the left-hander.

The familiarity between club and player could help New York’s case as well. Montgomery broke into the league with the Yankees back in 2017 and remained on the roster until 2022 when he was dealt to the Cardinals before the deadline.

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Unlike most other clubs on this list, the Yankees have some solid starting pitching depth. However, the oft-injured Carlos Rodón and 2023 breakout arm Michael King are far from “sure things,” and the club should happily add to their rotation corps at any chance they get.