Jed Jacobsohn/Getty Images
Looking for a solution at shortstop, a position of shortcomings and frustration since Orlando Cabrera's brief but wonderful stint in 2004, Theo Epstein locked up Julio Lugo for four years at $36 million after the 2006 season.
Alex Gonzalez had been Boston's shortstop in 2006, playing superb defense, however Epstein was looking for more offense.
Lugo played three seasons before he was DFA'ed and traded to St. Louis in 2009. Over his time in Boston, Lugo batted .251 with a .319 OBP.
Some offensive threat, huh?
Suffice it to say, Lugo never lived up to expectations. He had been a career .277 hitter (with a .340 OBP) prior to playing for the Red Sox. Lugo failed to ever hit 10 or some homers in a season with Boston, something he had done four times prior.
Gonzalez, meanwhile, signed with the Cincinnati Reds for three years at $14 million that offseason.
In a fitting twist in 2009, the Red Sox, after dealing away Lugo, picked up Alex Gonzalez in a waiver trade in August.
Not that Gonzalez was a prime option himself (he missed all of 2008), but he would have been a much cheaper and more productive option than Lugo.