Red Sox Free Agent Targets: Top 5 available hitters

PHOENIX, AZ - SEPTEMBER 27: J.D. Martinez /
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ANAHEIM, CA – SEPTEMBER 16: Justin Upton (Photo by Stephen Dunn/Getty Images)
ANAHEIM, CA – SEPTEMBER 16: Justin Upton (Photo by Stephen Dunn/Getty Images) /

Justin Upton

While Upton still has four years and $88.5 million left on his current deal, the contract includes an opt-out clause that can allow him to become a free agent this winter. MLB Network’s Jon Morosi reported earlier this month that it’s become increasingly likely that Upton will exercise that right to opt out. Morosi goes on to speculate that this could be a mechanism by which he negotiates more favorable terms on a new deal with the Los Angeles Angles, who acquired him in a mid-season trade with the Detroit Tigers.

While Upton’s preference may be to stay with the Angels, he could be swayed if their front office isn’t willing to pay him more than the amount that was left on his current deal. That could allow a team like the Red Sox to swoop in by offering more money on an average annual basis or tacking on additional years to the 30-year old’s deal.

Upton hit .273/.361/.540 over 152 games split between the Tigers and Angels. His .901 OPS was higher than any Red Sox hitter produced this season. It almost goes without saying that his home run total was as well. Upton blasted a career-high 35 homers, the third time in his career that he’s topped 30+ in a season. His 109 RBI were also a career high and more than any Red Sox hitter tallied.

The problem would be where to put him. Upton can play either corner outfield spot, primarily covering left field for the past few years. He’s still an above-average defensive outfielder, producing 8 defensive runs saved this season. He may not be open to the idea of becoming a full-time DH. Signing Upton would probably mean shifting Andrew Benintendi to center field and making Jackie Bradley a fourth outfielder/defensive replacement.

As much as the Red Sox could use Upton’s bat, the defensive downgrade that comes with removing JBJ from center offsets much of the appeal. As frustrating as the streaky Bradley can be at the plate, he still provides tremendous value with his glove. Unless the Red Sox trade Bradley, there doesn’t appear to be room in the outfield for Upton.

Editor’s Update: 11/2 – Upton opted out of his contract only to re-sign a new five-year, $106 million deal with the Angles, taking him off the market.