Batting Order
Comparing players by batting order seems much more logical than comparing worth by position. Jed Lowrie and Derek Jeter for example aren’t as comparable offensively with one as a bottom of the order hitter and one as a top of the order.

1st: Jacoby Ellsbury vs Johnny Damon
Small Edge Yanks

Ells might have a breakout year and eclipse Damon, or Damon could show his age more.

2nd: Dustin Pedoria vs Derek Jeter
Decent Edge Red Sox

Jeter is overhyped- but Pedroia may have had career year bringing it closer to even.

3rd: David Ortiz vs Mark Teixeira
Even

Ortiz may be declining, and Tex may blossom in Yanks lineup giving Yanks slight edge

4th: Kevin Youkilis vs Alex Rodriguez
Small Edge Yanks

Youk may have had career year and the edge may be larger

5th: J.D. Drew vs Hideki Matsui
Even

Drew may have to prove he can stay healthy- in which case may get small edge. Matsui needs to also play whole year and maintain stability to keep edge or remain even

6th: Jason Bay vs Xavier Nady
Small Edge Red Sox

Bay has had better years over Nady on same team, and Nady fared worse with Yanks after having possible career year in Pittsburg

7th: Mike Lowell vs Jorge Posada
Small Edge Red Sox

Both have serious health concerns- Posada is reaching age of catcher collapse and Lowell is reported to be recovering very well

8th: Jed Lowrie vs Nick Swisher
Even

Swisher has more pop- but Lowrie gets RBI’s very well from late batting spot and is a much better hitter for average

9th: Josh Bard vs Robinson Cano
Small Edge Yanks

Tough to know the Sox catching situation and thus project lineup- and it seems likely there will be some sort of platoon- but in any case (unless Sox get a good Texas catcher) it seems likely Cano will be better nine hole hitter- assuming he rebounds to previous career numbers

Rotation

1st: Josh Becket vs CC Sabathia
Small Edge Yanks

Both have Cy Young potential. CC has two 240 inning years that cause some concern- but has been very durable. This could go either way- but it seems most likely CC will be slightly better.

2nd: Jon Lester vs AJ Burnett
Even/Slight Edge Sox

Again this could go either way. You could argue both teams threes are better than the twos, or for the Sox that Lester may be the best. It seems very likely Lester will be better, but that projecting off of one complete year and it is very possible there could be a slight regression. Burnett needs to prove his durability.

3rd: Daisuke Matsuzaka vs Chien Ming Wang
Even

Again very tough call. Both aces that have gotten tons of wins (but wins for pitchers doesn’t mean much). Wang is coming back from an injury, and Dice-K is coming off a great ERA year full of walks and tough innings.

4th: Tim Wakefield vs Joba Chamberlain
Small Edge Yanks

Joba needs to prove he can go from 100 innings to 200 innings, but Wake has had some minor health concerns of late to make that concern less relevant for arguing who is better. Joba has better stuff but more question marks- Wake is very predictable for what he will produce if healthy and it’s solid for a fourth starter- but Joba has got a higher ceiling.

5th: Brad Penny vs Phil Hughes
Small Edge Sox

Assuming Penny and Hughes get the fifth spot gig it is tough to say who is better. Penny had a miserable injury plagued year- but his previous two years would compare well with either teams 1-3 big starters. Hughes didn’t fair too well last year either and really needs to prove himself in the bigs before he can be declared to have an edge even though his stuff is very good. Don’t forget how good Penny was two and three years ago- good discount signing.

Other:
Justin Masterson vs Ian Kennedy
Small Edge Sox
Likely sixth starter choices it seems. Masterson will be an eighth inning guy, but the Sox would likely want to keep Buchholz in AAA until he can come up and stay up. Kennedy had the same issue as Hughes except worse, and Masterson played great last year.

Clay Buchholz vs Alfredo Aceves
Decent Edge Sox

Buchholz may be a future ace but he too needs to prove himself. Despite his struggles, he has proven he has insane stuff, and it seems very unlikely and Yankees starter this low in the pecking order whether it is Eceves or anyone else could come close to competing with Buchholz.

George Kottaras vs Jose Molina
Even

Hard to know who the Sox backup catcher will be, but Molina will certainly be the guy for the Yanks. He can’t hit a lick, but he can play a mean defensive catcher. Kottaras seems to have a pretty good bat- but he has to prove it in the big club if that’s where he ends up.

Jeff Bailey vs Cody Ransom
Even

Two minor league unknowns. Both could end up in AAA as well.

Fourth OF: Gardner/Melky.
Hard to know if the Yanks will keep both OF’s, or if one may start if the Yanks make a trade which seems likely. The Sox could go internal (Van Every) or external (Kapler/Baldelli etc.), either way they will likely have similar production to the Yanks fourth OF, or possibly a slight Sox edge- a Kotsay resigning could also be possible.

Utility: 
Ransom may actually fit better in this spot for the purpose of this exercise, but in any case it is almost impossible to know who either team will use. Lugo may be stuck in Boston, but he would be a decent backup. Unless there are serious injuries in the infield for either teams (in which case it is likely a trade would take place to compensate) it seems likely the teams will have equally matched bench players.

Defense
Josh Bard vs Jorge Posada
Edge
Sox
Hard to know who the Sox play, but any pick is better than Posada especially if Varitek resigns. If Posada has to DH or gets hurt again Molina makes it pretty equal.

Kevin Youkilis vs Mark Teixeira
Even
Both are gold-glove guys. Youk’s flexibility to play third compensates for perhaps a very small edge to Tex.

Dustin Pedroia vs Robinson Cano
Decent Edge Sox

Cano doesn’t have great range and is quite average, while Pedroia is top third or above defensively at second.

Jed Lowrie vs Derek Jeter
Large Edge Sox

Lowrie is average or marginally above average at SS defense while Jeter is dead last or close to it at SS.

Jason Bay vs Johnny Damon
Even

Damon may have more range- but Bay plays a small LF for 81 games and has a much better arm. Damon also has to be healthy enough to play OF for it to matter.

Jacoby Ellsbury vs Nick Swisher
Large Edge Sox

No matter who the Yanks play at CF (Although Gardner appears to be very good out there) he won’t be as good as Ellsbury.

J.D. Drew vs Xavier Nady
Even

Both are average corner OF defensive guys, Nady probably covers more ground and Drew probably has a better arm.
These are of course very arguable- and this is just my take.

The SP1-3 spots are particularly intriguing. Which staffs stay healthy and avoid injuries will probably have better starting pitching production 1-3 as both teams have potential aces 1-3. The Sox have a much more starting pitching depth, especially with the Penny signing. Who knows, Sheets/Lowe/Smoltz/Kawakami still are linked to the Sox and any of those three signing would add a huge advantage to the Sox in pitching.

I really like comparing batting orders compared to fielding positions- I think it is much much more meaningful. I think the degree of advantages will be argued and there won’t be any consensus, but I think the overall advantages for each position seem very fair and unbiased. In addition, the qualifications to each judgment underneath spell out ways in which that advantage could change- and in fact many of the rankings could go either way- largely due to health or projecting if last year was fluky/career years for certain players.

I left out the bullpen since I think both will be very good and similar in production. Plus, this is the area that produces the most argument, and it can end up distracting from the rest of the post which I wanted to avoid.

Hope you enjoy this post.