Yankees Could Pay $100 Million for Reunion With Player They Gave Away

Getty Starting pitcher Jordan Montgomery was drafted by the Yankees in 2014, then traded away in 2022

After dealing starting pitcher Jordan Montgomery in the middle of the 2022 season, the New York Yankees are reportedly seeking to get him back — but it will likely cost the team much more than they received when they traded him away.

As the Yankees look to bolster their rotation this offseason and return to the playoffs in 2024, Montgomery has been tied to his former team in the latest free agency rumors.

“Montgomery could be an option for the Yankees, with whom he played until being traded to the Cardinals in 2022,” MLB.com reported. “New York has internally discussed a reunion with Montgomery this offseason.”

But such a reunion would probably mean offering a major, long-term deal: Kiley McDaniel of ESPN estimates that Montgomery will command a contract worth more than $100 million.

That could be a tough pill to swallow, especially since the Yankees have nothing to show for their trade return from dealing Montgomery in the first place.

Jordan Montgomery Has Proven The New York Yankees Wrong

GettySt. Louis Cardinals starting pitcher Jordan Montgomery faces his former team, the New York Yankees

The Yankees drafted Montgomery in the fourth round in 2014 and he made his debut in the Bronx three years later. As a 24-year-old rookie, he pitched for a respectable 3.88 ERA across 155.1 innings, but his next few seasons saw him limited to just 17 collective starts as he battled elbow injuries.

In 2022, in the middle of a comeback season where he struck out 158 batters in 178.1 innings, the Yankees traded Montgomery to the St. Louis Cardinals in exchange for Harrison Bader, a center fielder who they waived the next season.

“They might have given up on me, but I think it was the best thing for me to get to the Cardinals,” Montgomery later said, according to The Athletic.

In 2023, Montgomery pitched for a career-best 3.20 ERA across 32 starts. After being acquired by the Texas Rangers in exchange for four players, Montgomery went on to win the World Series, winning four pivotal playoff games for his new team.

It’s safe to say that the southpaw’s stock has risen since the Yankees let him go, and if they are going to get him back to the Bronx, they will likely have to pay much more than they might have if they had invested in their draft pick earlier. In March 2022, Montgomery signed a one-year, $6 million contract with the Yankees and the team could have almost certainly locked him up for longer had they known how he would end up realizing his potential in the years that followed.

At Least Six Other Teams in Contention to Sign Jordan Montgomery

GettyStarting pitcher Jordan Montgomery hoists the World Series trophy for the Texas Rangers in 2023

The Yankees might have some tough competition in getting Montgomery back, even if they are willing to admit they were wrong about the ace. According to ESPN’s Jeff Passan, numerous teams should be seeking to sign the lefty, including the New York Mets, Philadelphia Phillies, Boston Red Sox, San Diego Padres and Baltimore Orioles. 

The Rangers, once the frontrunners to re-sign Montgomery, appear to be slipping from the lead as they struggle to reach a financial agreement with their local television network brand.

“The Rangers made sense as a match for Montgomery, a key to beating the rival Astros in the ALCS, but their local TV issue may have put big expenditures on hold for now,” Jon Heyman wrote for the New York Post.