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

As the Boston Red Sox climb up the wild card standings and trade deadline dreams linger, their unimpressive offseason is at the back of fans' minds.

A fan-favorite offseason target was veteran pitcher and reigning World Series champion Jordan Montgomery. Days before the start of the season, he signed with the runner-up Diamondbacks and the hope that the Red Sox would make an impact move died.

Not signing Montgomery ended up being for the best. He's pitched to a 6.44 ERA over 13 starts of 65.2 frames with Arizona. He hasn't been the ace fans expected him to be, and he would be the worst starter in the Sox's rotation.

But the Diamondbacks have experienced a fall from grace since their World Series contending run last season. They're two games under .500 as of July 10 and their battling 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. And, 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 turned down a multi-year offer from the Red Sox and decided to hold out for a call from the Texas Rangers. That call never came, but even if it did, Boston is in a wild card spot, and Texas is not.

If Montgomery signed with Boston when it made him an offer, he could've had a spring training and he would've been coached by Andrew Bailey, who turned Tanner Houck into a bona fide ace. He also could've had job security this year, which is far from guaranteed after his outings with the D-Backs.

Like most other fans, reporters and insiders, Montgomery underestimated the Red Sox — although, ownership hasn't shown a change of heart when it comes to its approach to spending.

The emergence of Houck, Kutter Crawford and Nick Pivetta's successes from the mount made Boston's need for Montgomery obsolete. The Red Sox have been just fine without him, but the same can't be said for the lefty, who's having one of the worst seasons of his career in Arizona.

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