I would be strongly against retiring either Clemens or Wakefield's number, for different reasons. Clemens is a cheat and a carpet bagger, who happily betrayed Bosox fans by pitching so long and so well for rival teams after he let himself get fat with Boston. He never built the connection with the fan base that the other retired number players did.
Retiring Wakefield's number would be only out of sentimentality. He was a great guy who was with the team for ever, one of the twenty five, died too soon obviously, but he's simply not a player of the caliber where we should expect to see a number retired. Baseball Reference has his Red Sox WAR at 32.7, which is 24th is Red Sox history. That puts him behind the likes of Pedroia, Nomar, Tiant, Betts, Petrocelli, DiMaggio. And Wakefield compiled his total over 17 seasons, which is a lot more than any of those guys. Each of those players was better and more important in team history than Wakefield was. Are we going to retire all those numbers too? I'd guess Pedroia is the only one on that list with a shot (I figure they would have retired Tiant by now if that was going to happen).
Red Sox Hall of Fame, absolutely. Retired number, no way.