Jordan Montgomery is coming back to the Rangers. In the words of the Grateful Dead, what a long, strange trip it’s been.

The thirty-three-year-old right-handed pitcher spent six solid seasons with the Yankees, was traded to the Cardinals at the deadline of 2022, pitched well for Saint Louis, then traded to the Rangers at the deadline of 2023.

With Texas, Montgomery had his best stretch of baseball, going 4-2 in eleven starts with a 2.79 ERA. He won two of the four games against Houston in the Championship Series, including Game 7. He was the losing pitcher, though, in the only game the Rangers lost to Arizona in the World Series.

But he was a free agent at the end of 2023 and had one of those, long, protracted free agencies waiting for the right offer to come along. Finally, just two days before opening day of 2024, he signed a huge deal with Arizona. Not having had spring training, he started 2024 in the minor leagues, fired his agent Scott Boras for “butchering” his free agency, and then it all derailed. 

In 21 starts in 2024, Montgomery struggled, putting up a 6.23 ERA, missing a month with a knee injury, then being demoted to the bullpen.

Montgomery left the comfort of success with the Rangers and Mike Maddux for a two-year 45-million-dollar contract in Arizona. He was quickly vilified by the owner, who publicly stated signing Montgomery was a “horrible decision” and his biggest mistake as an owner.

The pain of those comments was followed by the pain in his pitching arm that required him to undergo Tommy John surgery in March of 2025, his second such surgery.

Yesterday, the Rangers signed Montgomery to a one-year, $1.25 million contract. He isn’t expected back until mid-season. 

Hopefully, his long-strange trip will come full circle and he’s pitching with the Rangers in the postseason once again. Hey, you gotta dream.