J.D. Drew
RF, Boston Red Sox
Deal: 5 years, $70 million
Few baseball players have enjoyed as much negative publicity from their relationship with Boras as Drew. The talented right fielder drew criticism from players and fans alike when he opted to play a year in the Northern League rather than sign with Philadelphia after the 1997 draft, holding out for a richer contract the next year.

After the 2006 season, Drew again became the subject of monetary controversy when he backed out of the remaining three years of a $55 million contract with Los Angeles to pursue an even larger deal with the Red Sox.