Left field is the biggest hole that the Red Sox need to fill this offseason, but there is still the issue at short. Here are the free agent shortstops from MLB Trade Rumors:

Orlando Cabrera (35) - Type A, can't be offered arbitration
Juan Castro (38)
Alex Cora (34)
Craig Counsell (39)
Bobby Crosby (30)
Adam Everett (33)
Chris Gomez (39)
Alex Gonzalez (32) - $6MM mutual option with a $500K buyout
Khalil Greene (30)
Jerry Hairston Jr. (34) - Type B
John McDonald (35)
Luis Rodriguez (30)
Marco Scutaro (34) - Type A
Miguel Tejada (36) - Type A
Omar Vizquel (43)
Jack Wilson (32) - $8.4MM club option with a $600K buyout

Quite a few familiar names on the list. The easy choice is to just pick up the option on Alex Gonzalez. He has a good glove and showed some improvement at the plate once he re-joined the Sox but I wouldn't do it. The name that jumps out at me is Bobby Crosby. Being out here in the Bay Area...