Yankees unlikely to land starting pitcher who’s holding a ‘grudge’ after previous trade

mlb: wildcard-texas rangers at tampa bay rays, jordan montgomery, yankees
Oct 3, 2023; St. Petersburg, Florida, USA; Texas Rangers starting pitcher Jordan Montgomery (52) reacts after striking out Tampa Bay Rays pinch hitter Junior Caminero (1) to end the seventh inning during game one of the Wildcard series for the 2023 MLB playoffs at Tropicana Field. Mandatory Credit: Kim Klement Neitzel-USA TODAY Sports

The Yankees have been connected to Jordan Montgomery on the free market in a potential reunion move. Montgomery is coming off a World Series win with the Texas Rangers, and while reports have indicated that he prefers to head back down south, money talks at the end of the day.

Montgomery is coming off his best season as a professional, pitching a career-high 188.2 innings this past season between the St. Louis Cardinals and Rangers. He enjoyed the collective 3.20 ERA, 7.92 strikeouts per nine, a 75.6% left-on-base rate, and a 43.2% ground ball rate.

Most impressive, he enjoyed a 2.90 ERA over 31 postseason innings, showcasing his quality when it mattered most. Obviously, the Yankees traded him away because they didn’t see the value of his services in the postseason, which Montgomery quelled with ease this past campaign.

In fact, Montgomery still has a sour taste in his mouth after general manager Brian Cashman traded him to the Cardinals in exchange for injured outfielder Harrison Bader. Montgomery wanted to help his team in the playoffs, and Cashman stole that opportunity away, so it is no surprise that he is still feeling some negative emotions toward the Bronx.

According to Randy Miller of NJ.com, Monty is still holding a grudge:

“They’re hearing he wants to stay with the Texas Rangers after winning a championship with them last fall. We’re hearing Montgomery still holds a grudge against the Yankees, who didn’t want him in their 2022 postseason rotation.”

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The Yankees are Likely Heading in a Different Direction

At the end of the day, if the Yankees are willing to give Montgomery a deal well above market value, he’s going to take it, even if his pride is hurt in the process.

At this point, it doesn’t seem as though Cashman is confident Monty wants to leave Texas, so he may settle for a fairer deal in hopes of running things back for the next few years.

Even if the Yankees did bring him back, Montgomery is now 31 years old and a long-term deal with undoubtedly experienced some hiccups down the road. The organization can’t afford to sign another pitcher to a bad contract, which is why Cashman is scouring the trade market, focusing on controllable pitching at a younger age.