I think Ortiz absolutely has a chance, but not necessarily on his merits (you have to basically ignore his entire time in Minnesota). It's not like Ortiz is some cuddly aw-shucks gentleman like, say, Andre Dawson, but rather he's pretty much the same candidate as Jim Rice (albeit with a sizable postseason bonus): Statistically under-qualified Boston player who hit like a beast for a while, but brings nothing else to the table. But that being said, the Red Sox are beyond amazing at that kind of PR, by far the best team in MLB and maybe the best in professional sports. I mean, they hired a PR person whose sole job responsibility
was getting Jim Rice into the Hall of Fame -- no other team, anywhere, ever, does things like that.
Of course, the door swings both ways ... if they decide they hate you (Francona, Nomar, Manny, Lowe, Pedro, etc.), they're masters at making their fanbase want to physically tie you up and burn you in front of the Ted Williams statue.