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MLB Trade Deadline: Worst Red Sox deals in history

By Sean Penney

Jul 5, 2016; Boston, MA, USA; Boston Red Sox president of baseball operations Dave Dombrowski speaks on the phone prior to a game against the Texas Rangers at Fenway Park. Mandatory Credit: Mark L. Baer-USA TODAY Sports
Jul 5, 2016; Boston, MA, USA; Boston Red Sox president of baseball operations Dave Dombrowski speaks on the phone prior to a game against the Texas Rangers at Fenway Park. Mandatory Credit: Mark L. Baer-USA TODAY Sports /
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Aug 15, 2015; Houston, TX, USA; Houston Astros former players Jeff Bagwell (left) and Craig Biggio (right) before a game against the Detroit Tigers at Minute Maid Park. Mandatory Credit: Troy Taormina-USA TODAY Sports
Aug 15, 2015; Houston, TX, USA; Houston Astros former players Jeff Bagwell (left) and Craig Biggio (right) before a game against the Detroit Tigers at Minute Maid Park. Mandatory Credit: Troy Taormina-USA TODAY Sports /

Jeff Bagwell for Larry Anderson – 1990

This is the trade that comes to mind when Red Sox fans preach caution of giving up prospects for a quick fix.

I’m cheating a bit here, as this trade actually took place as a waiver wire deal at the end of August, but it’s still the same idea. The Red Sox made a mid-season deal to bolster their bullpen by acquiring reliever Larry Anderson, but the ramifications of this decision would haunt them for years to come.

Anderson did a fine job for the Red Sox, posting a 1.23 ERA over 22 innings down the stretch. Unfortunately, that’s all they got from him, as he moved on after that season.

So for essentially one month of having Anderson in the bullpen the Red Sox gave up Bagwell, who became an iconic star for the Houston Astros. In his 15 year career, Bagwell hit .297/.408/.540 with 449 home runs. He won an MVP, a Gold Glove and made four All-Star appearances en route to compiling a resume that should eventually put him in Cooperstown.

Fans are quick to jump on any rumor that could potentially bring a difference maker that can help win this year, but the Bagwell trade offers a cautionary tale of why they should be hesitant to give up top prospects like Yoan Moncada and Andrew Benintendi. You consider it if you’re getting a sure thing that remains controllable beyond this year like Chris Sale, but anything short of a player of that caliber should be a non-starter for any deadline deal conversations involving those young studs.

Next: Trade Possibility: Hanley Ramirez

The reason why? They don’t want to be the team that gives up the next Jeff Bagwell in order to get a Larry Anderson type addition. Not again.

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