9. Fred Wilpon
TEAM (YEAR PURCHASED): New York Mets (1986)
W-L (WINNING PCT): 2,091-1,973 (.515)
COMPLEX SAYS: The Messropolitians have become known for bad signings, trades, firings, and just about every other front office fail since Fred Wilpon took over. After winning the World Series in 1986, the Mets have made just four playoff appearances and have had a few epic end of the season collapses. If that wasn't enough, in December of last year a lawsuit was filed on behalf of Bernie Madoff's victims claiming that Wilpon had actually profited from the Ponzi scheme. When bad meets evil, word to Em and Royce.