Johnny Damon, a key member of Boston's 2004 World Series championship team, filed for free agency on Friday along with second baseman Tony Graffanino. Damon hit .316 this year with 10 home runs and 75 RBI. The team's best relievers, Mike Timlin and Mike Myers, also are eligible to file, as are first baseman John Olerud, and reliever Matt Mantei. Graffanino, acquired midway through the 2005 season from Kansas City, was an upgrade at second base for the Red Sox but made a damaging error during Boston's playoff series loss to Chicago.