Well, to be fair, if you want to evaluate all pitchers, you need to evaluate those that will be here for a long time. And if we use CMW as a cutoff, then Beckett and DMats need to be in the equation.
For Boston
Beckett
DiceK
Buchholz
Lester
Masterson
Bowden
For NYY
Wang
Hughes
Chamberlain
Kennedy
Horne/Sanchez
I have maintained that Beckett vs Wang is a split simply because Wang has now been nasty for 2 and a half yrs now in this league and Beckett had a s*** yr last yr and has been a bit nastier this season. But after that, it is debateable.
Matsuzaka has the pedigree and the record behind him of being able to match-up against anyone and right now, our guy behind Wang for the future is Hughes. Right now, that matchup is pretty far in your favor. Hughes has significant room to improve, but so does DMats, so the advantage is well in the sox favor.
The future #3 as it stands would be Joba vs Buchholz. Both have been flat out dominant. Buchholz with his no-hitter and Joba without being scored upon yet in his career. In terms of upside, Joba has everyone on this list, but in terms of polish, Buchholz has him. This is a toss-up for now.
The future #4 stands as Kennedy against Lester and this is where I think we have the edge. I think Kennedy is a very safe pick to be a good to very good pitcher in the future, while Lester could be anything from very good to Casey Fossum level. Hence, this one goes our way.
In terms of future #5, the yankees have the best arm and the most polished pitcher. Sanchez has the best arm by far, but his future looks to be in the pen. Horne is the most polished pitcher at this juncture, but he is also much older than the sox duo here. Masterson, like Sanchez, looks to be a pen arm in the future. This leaves Bowden. He has the most upside as a starter in this category, but he also has the furthest to go. For right now, this one looks like it ends up the yankees way, but this will all depend on how Bowden develops and what the yankees do with Sanchez.