Two summers ago, when the Yankees traded Jordan Montgomery to St. Louis, CC Sabathia wasted no time in reaching out to the Cardinals legend, Adam Wainwright. On Friday, the Yankees’ legendary pitcher acknowledged that the trade left him emotionally shattered.

“I think I was more distraught over him getting traded from New York than kind of he was,” Sabathia told Daily News about the Montgomery trade. “I was upset about that. But just watching the way he’s responded, learning in St. Louis and then being able to come to Texas and pitch the way he’s pitched, it’s been great to see him kind of grow up. It’s like watching a little brother grow up.”

Sabathia described Montgomery as a seasoned veteran on the mound, emphasizing that he had accumulated a wealth of experience over time. He mentioned that Montgomery had faced a variety of challenges, including the pressures of pitching in New York and the expectations associated with being a Yankee. Sabathia noted that Montgomery had navigated through various ups and downs, ultimately emerging as a pitcher who had encountered and dealt with a wide range of situations and experiences.

Sabathia recalls Montgomery’s time in pinstripes

Sabathia recalled that when Montgomery initially joined the team, he was highly receptive to coaching and had a strong desire to expand his knowledge of the game. He mentioned the special dynamic between left-handed pitchers and described their relationship as being similar to the one he shared with Andy Pettitte, in which they spent a lot of time together, learning from each other. Sabathia pointed out that Montgomery adopted a similar approach, and their relationship had evolved to the point where they could discuss and analyze various aspects of the game, and sometimes, even unrelated topics. He characterized their relationship as positive and beneficial.

Sabathia, at 43 years old, mentioned that their bond has continued to grow and evolve as Montgomery, now 30, has experienced various life and career milestones, including getting married and approaching free agency.

But before Montgomery enters free agency, he has a season to complete. Following a trade during the summer, he joined the Texas Rangers and posted an impressive 2.79 ERA in 11 regular-season starts. In the postseason, he has continued to shine with a 2.08 ERA over his first 17.1 innings and three starts.

It’s worth noting that Montgomery has been wearing No. 52, which was Sabathia’s old jersey number, ever since he joined the Texas Rangers.

Sabathia mentioned that when Montgomery received the number 52, he reached out to inform him. Montgomery expressed his intention to wear the number 52 in honor of Sabathia’s remarkable second-half performance in Milwaukee during the 2008 season. Sabathia noted that Montgomery had continued to wear the number 52 to maintain that connection, and it had been a positive gesture.

Sabathia closely follows Montgomery

Soon after Montgomery was traded, Sabathia sent a text message to Adam Wainwright, asking him to look out for the pitcher. His primary concern was Montgomery’s comfort after the trade, as Montgomery had been a Yankee for his entire career until that point, and he asked Wainwright to take care of his “little brother.”

Wainwright graciously accepted and mentored Montgomery, just as Sabathia had done for the young pitcher in New York. Montgomery’s debut with the Yankees in 2017 quickly forged a strong bond between the two left-handed pitchers, and their friendship continues to this day.

Sabathia attended Montgomery’s first postseason start in Tampa, a seven-inning, scoreless gem during the Wild Card round. While he has been watching from home since Sabathia mentioned that he would make the effort to attend the World Series if Montgomery and the Rangers reach that stage.

Despite giving up four runs over four innings against the Orioles in the Division Series, Montgomery delivered an outstanding performance by shutting out the Astros for 6.1 innings in Game 1 of the ALCS.

In addition to his impressive postseason outings, the pitcher boasts a 3.17 ERA over 43 regular-season starts since his trade from the Yankees to the Cardinals in exchange for Harrison Bader. At the time, the Yankees were seeking a strong defensive center fielder, and they didn’t anticipate Montgomery cracking their postseason rotation the previous year.

Sabathia expressed that watching Montgomery was a source of stress for him, as he was emotionally invested in every pitch Montgomery threw. He commented that Montgomery had maintained a calm and composed demeanor, appearing as a determined and focused competitor on the mound. While Sabathia found it enjoyable to watch him pitch, he also felt a sense of stress because he had a strong desire for Montgomery’s success.

Meanwhile, the Yankees have been observing Montgomery’s impressive performances from home after failing to secure a playoff spot. Furthermore, they have faced criticism for the trade.

Sabathia shared his perspective, suggesting that the initial assessment or decision may not have been accurate. He indicated that for a pitcher to contribute in October, the team needs to be in the playoffs. Sabathia clarified that this was not meant as a criticism but rather an observation that the roster didn’t appear to be configured for Montgomery to participate in postseason play with his former team. He expressed his enjoyment in watching Montgomery’s performance throughout the current season and postseason. Sabathia also conveyed his hope that Montgomery would continue to excel and eventually partake in a championship parade.

Montgomery’s impressive performance after leaving the Yankees can be partially credited to his adjustment in pitch selection. He revealed on Sabathia and Ryan Ruocco’s R2C2 podcast last year that the Yankees had discouraged him from using his fastball. However, the combination of his fastball and his curveball, often referred to as the “Death Ball,” has proven to be highly effective, as highlighted by ESPN’s Jeff Passan in a recent report.

Sabathia is of the opinion that Montgomery’s composure and experience have played a significant role in elevating his performance to another level.

Coincidentally, the Yankees may look to bolster their starting rotation during this offseason. While they might prioritize other pitchers, such as Japan’s Yoshinobu Yamamoto.

When asked if Montgomery be amenable to reuniting with the Yankees, Sabathia expressed uncertainty about the specific destination but indicated that he liked the idea of his friend returning to the New Jersey area, and he found it appealing.

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