Bumped from a while back (and edited today based on recent events since the original post) and its something I like to discuss:

5 for Nomar
14 for Jim Rice, nobody has worn it since. EDIT: Retired this past year.
21 for Roger. nobody has worn it since. (Unlikely, but he was the face of the franchise)
24 in honor of BOTH D. Evans and Manny (Manny has zero chance now, Dewey a possibility since the current FO honors him every chance they get)
26 in honor of Wade Boggs (His Yankee days may hurt him)
33 in honor of Varitek. (Not sure with the way his career is winding down)
34 in honor or Papi (Once a possible lock, now not so sure)
42 in RED, rather than the blue Jackie Robinson 42 that currently resides on the facide in honor of the Hit Dog
45 in honor of Pedro Martinez (I think he has a chance, the bitterness has worn off)
47 in honor of Tito. If he brings in another WS title or two, then he deserves it down the road.
49 in honor of Wake, a no brainer in my mind.
58 in years to come for Paps (If he sticks around)

Im not suggesting all of them, or none of them...simply throwing out names who have contributed over 5+ seasons who might be worth considering.

Let the discussion begin.....