WAR is imperfect, yada yada, but he only had 26.7 as a Yankee. Dewey was obviously a far superior player with twice as much service to the franchises in question, but even if it's just about guys on multiple championship teams Wakefield had 34.5 with the Sox, Varitek had 24.2 and they'll never be retired. Pedroia was a far superior player with multiple titles and unless he makes the HOF or they make an exemption he's not getting retired either. If it's all about championships, why is Mattingly in?
I've posted this before, but it brings up a bit of a conundrum for me. I think some of the recent Yankee number retirements are a little silly... but I also think the Red Sox are too stingy about number retirements by limiting it to induction into the Hall of Fame. I know drawing bright lines is important, and I think the Yankees have cheapened number their number retirements by being overly inclusive, but I also think the whole "number retirement" genre does best when teams honor the players who were most important to their team and their fans, not purely the best players to ever wear the uniform.
Pedroia and Varitek are actually the perfect example of a small number of modern players who will never make the Hall of Fame, but whose Red Sox careers to me are worth memorializing through number retirements, especially because they won't get that same acknowledgement in Cooperstown. I'd also add Dewey Evans and there are other debatable ones (Jerry Remy, Tony C, etc.).
Take Varitek: 1,500 games in a Red Sox uniform, team captain, 2 World Series rings, entire ML career with the Red Sox, punched ARod. He'll never be the best catcher in Red Sox history because of Fisk, but I think he's worthy of a permanent place of honor within Fenway.
Again, I recognize it's a slippery slope, but the Yankees have retired I believe 21 numbers while the Red Sox have only retired 10 by my count (not counting Jackie Robinson). I don't mind somewhat formalizing a Hall of Very Good.
I said it was a better analogue (than, say, Trot Nixon). Not that it was exact.
Important player during multiple championships, known as a grinder, bit of a temper, not a star, had some moments.
I actually think Youk is a good comp, apart from not having played elsewhere for his entire 20s. He was never the best player on the Red Sox, but was always a fan favorite with a distinctive nickname. 3 All Stars and a Gold Glove vs. Paul's 4 All Stars for the Yankees, etc.