Boston Red Sox: Best players on the worst teams the last 20 years

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1996 – Mo Vaughn
Team record: 85-77 (third in AL East)

The ’96 Sox were coming off an AL East title but sank to third in Kevin Kennedy‘s second and final season on the job.

Pitching was an issue as Tim Wakefield fell back to Earth, Erik Hanson departed, and Aaron Sele failed to make the jump many had hoped for. The Sox kept trying to make “fetch” happen with Vaughn Eshelman and traded Jamie Moyer at the deadline for career fourth outfielder Darren Bragg.

Roger Clemens was solid by most metrics, got a hit in an April pinch-hitting appearance (the first since Tim Lollar in ’86) and had his second 20-strikeout game in September, but the headlines were dominated by his uneasy relationship with GM Dan Duquette heading into free agency. Though Duquette implied Clemens was in the twilight of his career (40-39, 3.77 the previous four seasons), the “Texas Con Man” would resurface in Toronto with a fat contract and a new “workout regimen” to soar to new heights the following season and beyond.

Duquette continued to forge a reputation for having busy rosters, employing more players than any other GM in baseball, among them Milt Cuyler, Jose Malave, Arquimedez Pozo and Rudy Pemberton. This approach did yield one gem, as Rich Garces hooked on with the Sox in ’96. The portly reliever known as “El Guapo” went on to become a fan favorite in parts six seasons in Boston.

’96 was also the curtain call for “The Gator,” Mike Greenwell, who exited with an incredible nine-RBI game against the Mariners that September.

Though Reggie Jefferson hit .347 as a platoon player and several other Red Sox contributed solid offensive outputs, Mo Vaughn’s MVP encore went one better than his award-winning ’95 season: .326 with 44 homers and 143 RBI. “The Hit Dog” cranked out 207 hits and posted a career-high .420 on-base percentage in another All-Star campaign.

Two years later, Vaughn would follow Clemens out the door in another discordant veteran departure from Boston. However, the Red Sox were eventually proven right by not shoveling money at the free agent, as injuries prevented him from ever again approaching his Boston numbers.