Major League Baseball

Jordan Montgomery was a playoff hero. It will pay off for him in free agency

Published Nov. 13, 2023 7:45 a.m. ET

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Deesha Thosar

MLB Writer

Major League Baseball clubs may find slim pickings for starting pitchers on the open market this winter. The starting-pitching market is competitive enough that some teams may make desperate trades. But first, the top free-agent starters are still on the board. 

Among those few sought-after free-agent arms is southpaw and World Series winner Jordan Montgomery. The 30-year-old entered free agency at an opportune time — days after he helped lead the Texas Rangers to their first-ever championship. 

Montgomery wasn't just collecting bench splinters during the Rangers' playoff run; he was their ace behind Nathan Eovaldi. Montgomery posted a 2.90 ERA across 31 innings and six playoff games (five starts), including tremendous outings against the Tampa Bay Rays and Houston Astros. 

Montgomery shined even before the postseason limelight. Only one left-hander, Houston's Framber Valdez, threw more sinkers or two-seam fastballs this year than Montgomery. And among lefties with at least 500 sinkers or two-seam fastballs thrown, only the Marlins' Braxton Garrett held righties to a lower batting average (.244) than Montgomery (.245). 

Now, with Arlington's World Series parade behind him, Montgomery is one of a handful of top starting pitchers exploring free agency. Backed by agent Scott Boras, he should be highly coveted. Montgomery's makeup makes sense for just about any team. His 2023 base salary of $10 million should be doubled each season (at the very least) over the next five or so years.

"Jordan did a lot in the postseason," Boras told reporters at the GM Meetings. "The Everest for the Rangers was beating the Astros and Jordan had three remarkable performances with a 1.29 ERA. Owners are clamoring for us to, 'Let's make a deal on Jordan.' I think all owners are all very, very aware that he's worthy of a Monty Hall."

The super-agent said Montgomery is entertaining offers from all clubs. Boras also compared his client to Jon Lester, Cole Hamels and Andy Pettitte. Those are some aspirational left-handed comps for Montgomery, no doubt. Still in his prime, Montgomery has several years to make the case that he's just like those decorated (and durable) pitchers. But, as things currently stand, Montgomery is more of an Aaron Nola.

Nola and Montgomery, who are both 30 years old, debuted in the major leagues around the same time, with the former making his first MLB start in 2015 and the latter first appearing in 2017. In that time, Nola has logged almost double the amount of innings as Montgomery. But, since 2021, both Nola and Montgomery have made 96 and 94 starts, respectively, across 579.1 and 524.1 innings.

Jordan Montgomery on Rangers defeating Astros in ALCS to advance to the World Series

Nola has a 4.09 ERA in that span while Montgomery has a 3.48 ERA. Nola's 1.077 WHIP since 2021 is slightly better than Montgomery's 1.184 WHIP. Nola has also given up more home runs (77) than Montgomery (58) since 2021, and he's struck out more batters in that span, but their walk rates are similar and their reputations as sturdy starters are also comparable. 

Montgomery will likely earn a similar contract to whatever Nola accepts in free agency this winter. Nola, who owns the fourth-best pitching WAR (per FanGraphs) in MLB since 2017, is expected to earn slightly more than Montgomery. Both arms will likely land a deal in the five or six-year range, with an average annual value for each arm somewhere between $22-30 million. 

Montgomery setting himself up for a bigger payday has been at least two years in the making. 

He switched from being represented by the Beverly Hills Sports Council to the Scott Boras Corporation in Sept. 2021. Less than a year later, the Yankees traded him to the Cardinals in exchange for outfielder Harrison Bader. General manager Brian Cashman, at the time, said part of the reason Montgomery was no longer a Yankee was because the front office believed he wouldn't be a factor for the club in the playoffs. At the time of the 2022 trade deadline, the Yankees favored offensive help over pitching depth. 

The Yankees ended up getting swept by the Astros in the American League Championship Series to end their 2022 season. Gerrit Cole, Nestor Cortes, Luis Severino and Jameson Taillon all started in that ALCS, combining to give up 10 earned runs over 16.2 innings (a 5.40 ERA). That same October, Montgomery pitched 2.2 scoreless innings in relief for St. Louis. The Cardinals were swept by the Phillies in the National League Wild Card Series. 

Last year didn't end how Montgomery or the Yankees would've wanted, with neither he nor his former team lifting the championship trophy. But this October, it was Montgomery who held the Astros to two earned runs in three ALCS starts on the way to winning the World Series. It was the Yankees, eliminated from playoff contention for the first time in seven years, who were left wondering what could've been. 

Could both of Montgomery's former teams be in the mix to sign the southpaw? The Cardinals have been linked to Montgomery in free agency, and the Yankees certainly need pitching depth now, even if they didn't one year ago. But as Boras said, St. Louis and New York are not the only major clubs interested in the southpaw. The Red Sox also reportedly met with Montgomery ahead of this year's GM Meetings. The Dodgers and Mets need starters to fill out their rotation, too.

It will be interesting to see how high executives are willing to go for Montgomery, particularly in a diminished starting pitching market this winter. He just shouldered the biggest workload (188.2 regular season innings, plus 37.2 playoff innings) of his career. His 4.3 fWAR tied for 13th-best in MLB this season. His fastball velocity has climbed over the years. His 21.6% strikeout rate wasn't spectacular, but his filthy curveball was. As things currently stand, it would be surprising if Montgomery struck a deal equal to Carlos Rodon's with the Yankees last winter (six years, $162 million). Then again, it wouldn't be the first time a team overpaid for a starting pitcher. 

While we don't yet know how teams will value him, we do know this: Montgomery is coming off the best year of his life. Now, he's approaching what will be the biggest contract of his life, too.

Deesha Thosar is an MLB writer for FOX Sports. She previously covered the Mets as a beat reporter for the New York Daily News. The daughter of Indian immigrants, Deesha grew up on Long Island and now lives in Queens. Follow her on Twitter at @DeeshaThosar. 

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Deesha Thosar