For whatever reason, I’ve been having a large number of conversations about Red Sox retired numbers lately. From students trying to get me on a tangent by asking who they all are to discussions about whether Pedro Martinez’ return on Opening Day was a play to get 45 on the facade, the frequency of the topic has gotten me thinking about what the next number retired would be. So, instead of the usual recriminations or wishful thoughts on the 2010 campaign, I wanted to run down the top five candidates in order of what I think is their likelihood of retirement. I don’t expect everyone to agree, but it should spark some interesting conversation.

The current list stands at 1, 4, 6, 8, 9, 14, and 27 (along with Jackie Robinson’s 42). Bobby Doerr, Joe Cronin, Johnny Pesky, Carl Yastrzemski, Ted Williams, Jim Rice and Carlton Fisk — as good a rundown of Red Sox greats as you can get. Hall of Famers all, aside from Pesky, who represents a special case. The restrictions on retirement have been eased by current ownership, and the rules are now a bit fuzzy; it used to be that a player had to begin and finish a Hall of Fame career with the Sox. That seems to no longer be the case, despite a few acrobatic moves to get Fisk there. So, with that in mind, here is my list of five, along with their numbers, chances and qualifications.

5: Dustin Pedroia, 15 – 500 to 1
I debated which current players had the best chance of winding up on this list. Kevin Youkilis, Pedroia, Jon Lester and Josh Beckett would seem to be the most obvious picks on the current club; David Ortiz would have led the conversation a couple years ago, but at this point it seems pretty unlikely. Assuming that the player in question will wind up in the Hall, Pedroia seems to be the best choice. Already a Rookie of the Year, MVP and two time All Star by the end of his age 25 season, he still is heading toward his prime. At second base, he’s facing some less than stellar competition (despite the 2B renaissance of the current AL East). If he continues at his current pace, he would almost certainly wind up with Hall of Fame quality numbers — somewhere in the neighborhood of 3000 hits and anywhere between 150 and 250 HR with the kind of OPS he’s been posting would easily be enough to get him there. Obviously there’s far from a guarantee, which is why I’ve put his chances so low; I also have doubts about how long he can keep up his current pace given his body type and the amount he relies on incredible bat speed. When that starts to slow — which admittedly shouldn’t be for at least another five seasons — he might go downhill fast. Still, given his track record, age, and position, he just gets the edge on Lester here.

4: Curt Schilling, 38 – 200 to 1
There are a couple possible stumbling blocks here. The first is that I am not at all convinced Schilling will reach the Hall of Fame. His numbers are borderline; if he got in it would be on the back of his three championships and his reputation as a big-game pitcher. He’s a step above Jack Morris, another excellent big game pitcher with career numbers that may fall just short. If he is voted into the hall, though, a debate of another sort begins. Schilling only played five seasons with the Sox, and 2008 barely counts (he was under contract but never pitched a game). Is that long enough to retire a number? Under normal circumstances, it would fall far short, but Schilling obviously occupies a very special place in Red Sox history. I personally wouldn’t either vote for his Hall candidacy or put his number on the wall, but I can see my way clear to the opposing arguments.

3: Wade Boggs, 26 – 100 to 1
Half of you are already telling me I’m an idiot for this, but Boggs is arguably the greatest Sox position player who is not already on the wall, and with a Hall of Fame plaque already in place he meets the apparent requirements. It wouldn’t be too hard for the Sox to bring him back a la Fisk to keep up appearances. Boggs’ credentials are impeccable — there’s no reason to keep him off that has anything to do with his time here as a player. The only argument is, essentially, that he went to the Yankees and that a significant portion of the fanbase still doesn’t like him, for reasons ranging from personality issues to a bizarre conception that he was a ‘selfish’ player. On the first count, it’s true — he did sign with the Yankees. But they paid him, and the Red Sox refused to; that decision, in my mind, rids him of any stain of wrongdoing. Of all the names on this list, I think Wade Boggs is the most slam dunk case. The only reason his chances remain low is because of the fan reaction to him — an unfair one which I hope will fade in time and allow him to take his rightful place.

2: Jerry Remy, 2 – 50 to 1
The more I think about this, the more I become certain it will happen. Remy would be far from the first announcer to have something retired by the team he served; obviously Remy’s playing time doesn’t come close, but I expect that when he hangs up the microphone he’ll get the Pesky treatment. He’s as close to a franchise announcer as the Sox have, and while he doesn’t have the national cachet of Ernie Harwell, Harry Caray or Vin Scully, he is synonymous with the Red Sox in a way few others are.

1: Pedro Martinez, 45 – 2 to 1
To me, this is the only true slam dunk here. Pedro’s 45 will, I think without question, one day grace the right field facade. As soon as Pedro is inducted into the hall, he’ll be back for a Pedro Martinez day that I’d sell several choice internal organs to attend. I’ve already written extensively about Pedro’s tenure with the Sox on this site; suffice it to say that no other ballplayer has ever come close for me, and I don’t expect any ever will. Pedro gave us the two greatest pitching seasons ever seen. He, more than any player aside from Nomar Garciaparra, made the Sox the incredibly popular franchise they are today. Without him, we don’t win in 2004, and we likely don’t even win in 2007 — the impact he had on this club will reverberate for years. He still owns the greatest winning percentage in Sox history, and authored some of the finest moments in the modern era. His number belongs there more than anyone else I can think of. How about you?