MLB insider reveals Jordan Montgomery’s massive mistake with Red Sox in free agency

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As the Boston Red Sox make their way up the wild card standings and trade deadline hopes remain high, fans have largely forgotten about their lackluster offseason.

One popular target during the offseason was veteran pitcher and reigning World Series champion Jordan Montgomery. However, just days before the season began, he signed with the runner-up Diamondbacks, dashing Red Sox fans’ hopes for a significant acquisition.

In retrospect, not signing Montgomery turned out to be a good decision. With a 6.44 ERA over 13 starts and 65.2 innings for Arizona, he hasn’t lived up to expectations and would have been the weakest link in the Red Sox rotation.

Jordan Montgomery makes D-backs debut; Southpaw twirls six innings opposite  Blake Snell in first start of 2024 - CBSSports.com

The Diamondbacks, too, have faced a decline since their strong World Series run last season. As of July 10, they are two games under .500 and fighting for a National League wild card spot.

Jordan Montgomery had the chance to sign a muti-year deal with the Red Sox, but turned it down

They’re far from the “winning team” Montgomery hoped to play for. Surprisingly, the Red Sox have become a contender. Montgomery had the chance to play in Boston, but he turned it down.

According to MLB insider Jon Heyman, the southpaw rejected a multi-year offer from the Red Sox, holding out for a call from the Texas Rangers. That call never came, and even if it had, Boston is in a wild card spot, while Texas is not.

3 teams that should buy low on Jordan Montgomery at trade deadline

Had Montgomery signed with Boston, he could have gone through spring training and been coached by Andrew Bailey, who transformed Tanner Houck into a bona fide ace. He also would have had job security, which is now uncertain given his performance with the Diamondbacks.

Like many fans, reporters, and insiders, Montgomery underestimated the Red Sox. However, ownership hasn’t shown a change of heart regarding its spending approach.

The emergence of Houck and Kutter Crawford, along with Nick Pivetta’s success on the mound, made Boston’s need for Montgomery obsolete. The Red Sox have thrived without him, but the same can’t be said for Montgomery, who’s having one of the worst seasons of his career in Arizona.

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