25. Mo Vaughn

Year: 1999
Contract: $80 million/Six years
Team: Anaheim Angels
Mo Vaughn's 40 home runs and 100-plus RBI seasons with the Red Sox made many consider him one of the Greatest Fat Baseball Players of All Time. Those numbers also got him the biggest MLB contract in the league in '99, but two productive yet non-stellar seasons with Angels, a season-ending knee injury, and battle with the bulge made those glory days in Boston a distant memory. He was later traded to the Mets where he continued to decline and ruin his rep. Oh yeah, that mention in the Mitchell Report years later didn't help either.