TEAM (YEAR PURCHASED): Kansas City Royals (2000)
W-L (
WINNING PCT): 1,167-1,574 (.426)
The former Wal-Mart president was the Royals CEO for seven years before becoming the sole owner in 2000. Under Glass' ownership, KC hasn't made the playoffs and been over .500 just once. His frugal tendencies have allowed stars like Johnny Damon and Carlos Beltran to slip away without making any blockbuster acquisitions in return. That cheap skate Wal-Mart shopper steez doesn't work in the MLB, fam.