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Manny - I have no idea what the Sox will do. if he'll resign for $15M, the Sox will bring him back. If it takes $20M, they won't. In between, i dunno.
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Aside from Boggs, and (gulp) Clemens, Ramirez is probably the only player with a good chance of seeing his number retired by the team. His contract runs out after 2008, which would be his eighth season in Boston. That leaves him just two years short of the magic ten. Now the Red Sox do have 9th and 10th option years for $20 million, and maybe they'd like the idea of going year to year with him in 2009 and 2010. I just figure that they'll want to invest that $20 million elsewhere. There's been so much bad blood between Ramirez and management that I can't imagine the Red Sox voluntarily extending his tenure with the team. I also don't see Ramirez electing to stay here if the Red Sox decline his option for 2009. He's wanted to go out west for awhile now, and the Angels would probably be a good fit for him. Maybe they'd sign him for 4 years/$60 million.
Our best chance of seeing Manny's #24 up on the rightfield wall is to continue overpaying him in 2009 and 2010, as a trade-off for losing him to a competitor, or being pushed into making a commitment beyond the two option years. Then we'd need him to retire after 2010 so that he's ending his career as a Red Sox player after 10 seasons of play. In 2015, he'd then be inducted into the Hall of Fame and he'd meet all the team's requirements. I hope it works out this way - I just don't expect it to be the case.
With Pedro, I have a strong feeling that the Red Sox will bring him back here in some capacity after his contract runs out with the Mets. Maybe he'd return on a one year deal as a 4th/5th starter, and then spend two years as a spring training instructor so that he reaches the requisite 10. I know that's a bit of a stretch but I think Red Sox fans have a greater affinity for Martinez than for Clemens.