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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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A painful reminder of the worst trade deadline deals that the Boston Red Sox have ever made.

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 /

The MLB trade deadline is rapidly approaching, leaving the Boston Red Sox little time to make the type of significant upgrade to the roster that could become a difference maker in a tight division race.

Red Sox Nation is imploring Dave Dombrowski to make a splash with another bold move that he’s become famous for. The win-now mentality in Boston drives the temptation to empty the cupboard of their stacked farm system to bring in a star caliber player that improves the team’s chances of winning the World Series in 2016.

Sacrifice tomorrow for today.

Sometimes these decisions actually work, as the list of recent champions is littered with teams that made crafty moves to upgrade at the deadline. Last year it was the Kansas City Royals, who needed an ace to front their rotation and acquired Johnny Cueto to fill that void. While Cueto didn’t live up to his lofty standards during his time in the American League, he was still a massive upgrade over their alternative options and proved to be enough to put the Royals over the top.

This is the time of year where teams are forced into two camps – buyers and sellers. The Red Sox have been both at various times throughout their storied history, but there are a number of occasions when they should have been neither. Whether it was a botched attempt to upgrade the roster with a player that never panned out, a prospect they surrendered that turned out to be far too valuable to have let go or an attempt to sell that didn’t bring back the return they expected, the Red Sox have made their fair share of bad trades over the years.

Sometimes the best moves are the ones you don’t make. Here is my list of the mid-season trades that the Red Sox should have thought twice about.

Next: Gagne

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