He deserves to have records for appearances, innings and other things that would reflect his durability. However, for him to have the distinction of the Winning-est pitcher in Red Sox history is completely misleading and it misrepresents his contribution to the Red Sox. The record for wins for an original franchise like the Red Sox conveys a level of excellence. Wakefield has not been an excellent pitcher. He has been consistently mediocre throughout his career and very inconsistent from game to game (and even within games) throughout his career. He has never, in his long career, been the Red Sox stopper or ace. He has never been even the second best pitcher on any Sox team, except for an improbable run during 1995. There may have been a year or two where he had the best or second best stats on the team, but he was never the top guy or number 2 guy. In a number of years he barely made the starting rotation.
In my four and a half decades, I can think of many many pitchers who have had more excellent Red Sox careers. Obviously, if he gets the record, it's his achievement, but the Sox should make no extraordinary effort to keep him on the team in the hope that he gets the record, because in my opinion, he's not good enough to hold that record.