Taking the roster position-by-position:
Keep 'em crossed that Hip Hip Jorge is able to catch 100 games in 2009, and the Molina holds up for the other 62. Francisco Cervelli is the next option; let's hope he gets to take the full year at AAA.
An upgrade here is a must. Trading for Swisher is a nice move, but I would like to see him as a 4th OF, back-up 1B rather than the everyday guy. Texiera is the obvious first choice. A 7 year $155mm deal should get it done. Other options are extremely limited - Prince Fielder, Ryan Howard, and Adriane Gonzalez may be attainable, but would prove to be far too expensive in terms of prospects.
Target - Tex
2B - Robbie
Corner OF -
We are flush at the corner OF positions with less than spectacular options. Hmat, Damon, Nady and Swisher would all be vying for time if the season started today. While adding Manny to play RF would make for one hell of a lineup, that simply is not going to happen. Provided we get Tex we could live with the 4 of these players for 3 spots (RF, LF, DH). I expect we would see some drop off from both Hmat and Damon, but they would still be quite productive players IF they stay healthy. Swisher should rebound from an abysmal season to something around 250/27/90 390 OBP. Nady was on the cusp of a breakout season when traded to the Yanks last year; I think he will continue that break out now that he's more comfortable being a Yankee. I see 300/25/100 from the X man in 2009.
CF - Gardner/Melky. With AJax coming in '10, there's no reason to make a move in CF for '09. I start Gardner there and see if he can get on base enough to be a royal pain in the ass when he does. If not, we know Melk will play a plus CF and hopefully hit better than 250.
The big move is obviously getting CC in pinstripes. Assuming that gets done, my next move would be to get Ben Sheets. While everyone has been talking about AJ Burnett, I think the better sign would be Sheets. He is 2 years younger than AJ, and if we are going to take a flyer on an injury prone starter I would rather it be the younger guy. Both Sheets and Burnett have the ability to be a top of the 'ro guy if healthy. Having spent his career in the NL central pitching in such parks as Wrigley and Minute Maid, his numbers should only be about half a run worse in the AL east. Rounding out the rottion with Andy , Wang and Joba would leave a starting 5 of -
1 - CC
2 - Sheets
3 - Wang
4 - Pettitte
5 - Joba
6. Hughes, Aceves, Geiss
In order to execute we would need the following signings (with anticipated deals)
CC - 6 years, $150mm ($25mm/yr, 34 at contract end)
Sheets - 4 years, $70mm (4th year vests based on IP) ($17.5mm/yr, 33 at contract end)
Texiera - 7 years, $165mm ($23.5mm/yr, 36 at contract end)
Pettitte - 1 yr, $11mm (old)
These 3 deals cost the Yanks a total of $77mm per year; well below the $88mm that came off the books after the season. In terms of payroll, my plan is not a problem.
The potential problems to executing would be an inability to sign any of the free agents I listed; Tex might want to take the Angel's money, CC might want to be a hitting pitcher on the west coast, and Sheets might want to go to the pitcher's haven in Atlanta. Barring any of these guys pulling a Greg Maddux, however (Maddux took less money from the Braves than the Yanks offered when he left Chicago), the Yanks could, and should get each one.