I know it's early and there is so much that can change from now until 2010, but the early signs are obvious.
Matt Holliday or Jason Bay will be with the Yankees in 2010.
I know, total speculation. There is no unnamed source or friend of either guy that I am basing my guess off of. Instead, I came to this conclusion simply by looking at the Yankees performance during this off season.
Entering this off season, the Yankees were down to only two definite starters (Wang and Chamberlain) and were determined to add the best starting pitchers their money could buy. Luckily for the Yankees, they had more than $80 million coming off the books (including the contracts of SP Mike Mussina, SP Carl Pavano, SP Andy Pettitte), which gave GM Brian Cashman plenty of ammo to go after CC Sabathia and AJ Burnett.
Now let's fast forward to next winter when the Yankees will clear at least $32 million bucks in payroll. The following Yankees will all be free agents after the 2009 season:
OF Johnny Damon ($13 mil)
OF Xavier Nady ($6 mil)
OF Hideki Matsui ($13 mil)
Hmmm...now what do all those guys have in common? Why yes, all three are indeed outfielders, which would leave the Yankees with Melky Cabrera, Brett Gardner, Nick Swisher (assuming he's not traded), and a bunch of minor leaguers (namely Austin Jackson).
So with more than $30 million bucks available and two (maybe three) outfield spots to fill, can we really expect the Yankees to do anything but throw a ton of money ($10-$15 mil per season) at either Jason Bay or Matt Holliday? I cannot think of one reason why not. Both guys are young, productive, and will be in their prime for years to come. The Yanks have a pretty good track record of throwing a boatload of money at the best free agents on the market.
Holliday and Bay will be no different. Once the 2009 season ends, it will come down to which player the Yankees covet more and how much additional money the Yankees are willing to dish out.
Mark my words: it's only a matter of time.