If Mannys option years get picked up, #24 I see as a real possibility.
Everyone else is going to fall short in criteria tho.
Petey got a WS, but was not in Boston for 10 yrs. 20%
Clemens, absolutely no chance at all. Especially after recent speculation. And lets not forget, Roger was really good for the Sox for awhile, but his last 3 or 4 seasons in Boston where very unspectacular. Alot of why Clemens was thought of as such a great pitcher, was for after he left Boston. 0%
Nomar, no chance. 0%
Tek will be a fan favorite and beloved by all of RSN forever but I'd say 15% chance of getting retired.
Schilling, not enough time in Boston, 5%
Wak, interesting dilema here. Waks been in Boston for awhile, although hes no HOF and never had huge season, hes always been there and usually given alot of quality. Hes always been a team 1st guy and a modle citizen. 30% chance.
Ortiz. This is really tough, and of all the above mentioned Papi is the one player the the rules might be completely bent or broken for. If Ortiz stays with the Sox for the rest of his career he has a shot. 2 WS titles helps, but there something different about Papi. He might not be a HOF, but you could argue he might be the biggest clutch hitter ever. Because of these clutch hits, he has become a super star of the game and a living legend in New England, and all other parts of RSN. Big Papi like Williams,Yaz, and Peskey will forever be linked to the Sox. 50% chance.