Agent pitches Montgomery as the next Andy Pettitte with an eye on Yankees

Ex-Yankees and current Rangers' starter Jordan Montgomery with the 2023 World Series trophy at Phoenix, AZ, on November 01, 2023.

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Yankees fans still remember former ace Andy Pettitte as their most consistent rotation leader. But super agent Scott Boras sees Yankees castoff Jordan Montgomery as present-day Andy Pettitte.

“Jordan Montgomery is the modern-day Andy Pettitte — mentally and emotionally,” Scott Boras told on The New York Post’s “The Show” podcast.

Although Montgomery wrapped up the regular season with an impressive 3.20 ERA in 188 2/3 innings, following his trade from the St. Louis Cardinals to the Rangers, his postseason performance further highlighted his worth. The 30-year-old has become a free agent this offseason and comparing him to the ex-Yankees ace is an attempt to draw the team’s interest.

Pettitte analogy part of Boras’ pitch to sell Montgomery

Scott Boras is the baseball’s most prominent salesman. Following the conclusion of the World Series, free agents are now permitted to engage in discussions with other teams, although they must wait until November 6 to officially ink any contracts.

But Boras has initiated an aggressive promotional campaign for Montgomery. To make the influence felt, he drew a comparison that resonates with New York Yankees fans on various levels while discussing a specific player who is expected to secure a substantial, multi-year contract this offseason.


The prominent agent didn’t refrain from pushing Yankees fans to seek Montgomery, who had a six-season tenure with the team before being traded to the Cardinals in 2022. He examined the pitcher’s situation by referencing the Yankees’ negotiations with Gerrit Cole following the 2019 season, during which they included Andy Pettitte in the meetings to advocate for New York.

This experience prompted the super agent to establish a connection with Pettitte and contemplate the qualities that contributed to Andy’s excellence. Boras recalled their conversation, noting that Pettitte possessed a unique postseason mentality and a deep understanding of spin and batters’ counts, qualities that Montgomery shares.

Boras mentioned that Pettitte had a history of winning significant games, and he drew a parallel to Montgomery, stating that the pitcher possesses a similar dynamic.

During his 15-season career with the Yankees, Pettitte amassed a remarkable 19-11 postseason record, maintained a 3.81 ERA, and clinched five World Series titles, all of which were achieved with the Yankees.

In the postseason, he made six appearances, five of which were starts, totaling 31 innings. During this period, he secured a 3-1 record with a 2.90 ERA. Notably, he pitched three times in the ALCS against the Houston Astros, winning twice, including a pivotal relief appearance in Game 7 where he delivered 2 1/3 scoreless innings. In the only World Series game he started, Texas faced defeat as he conceded four runs in six innings.

Impressively, this performance comes from a player whom the Yankees initially believed wouldn’t be a part of the team’s postseason rotation, leading to his trade at the 2022 deadline.

Jordan Montgomery with his wife McKenzie Dirr at Yankee Stadium, New Yor, in 2021.

Will the Yankees get back Montgomery?

Drafted by the New York Yankees in 2014, Montgomery embarked on his Major League career with the storied franchise in 2017. He spent several seasons in the Bronx, delivering some solid performances before the Yankees decided he was expendable, trading him to the St. Louis Cardinals in 2022. His Cardinal stint lasted only a year when he was dealt again, this time to the Texas Rangers in July. Since joining Texas, Montgomery has significantly bolstered their bullpen.

His effectiveness was on full display in Game 1 of the American League Championship Series against the Houston Astros. Montgomery was masterful, tossing 6.1 scoreless innings in the Rangers’ 2-0 victory. A highlight was his striking out a batter to strand three Astros on base in the fourth, earning immense praise.

On the eve of starting Game 2 of the World Series, Montgomery softened his stance on his former club. In an interview Thursday at Globe Life Field, he stressed seizing opportunities as being critical to success. He expressed confidence in handling big games, dating to his high school, college, and minor league days. He simply needed a chance to showcase his talents.

Montgomery revealed that many ex-Yankee teammates contacted him during the playoffs, including Gerrit Cole, Aaron Judge, and Aaron Boone. He still has ample supporters in the New York clubhouse, likely explaining his lack of ill will over being traded.

Even former ace CC Sabathia feels the Yankees erred in trading Montgomery. He described Montgomery as a seasoned veteran on the mound, having accumulated valuable experience over time. He mentioned Montgomery enduring various challenges, like the pressures of New York and Yankee expectations. Sabathia noted Montgomery navigated ups and downs to emerge battle-tested and able to handle diverse situations.

Jordan Montgomery playing a game with Texas Rangers.

A throwback to social media posts linking Montgomery to Pettitte

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