I was wondering about this also. Could they renegotiate the existing contract to "front end" some money to 2013, plus tack on a reasonable extension (perhaps consisting of option/buyout years)?
You can't "front-end" the agreement -- unlike the NFL and NBA, MLB uses AAV rather than cash flow to determine the annual luxury tax impact of contracts.
But, if you signed Pedroia to a 3/45 extension before Opening Day, I suspect you would lump that together with the two years remaining on his current year (disregarding the option) and amortize it as 5/65 -- which would shift a portion of the luxury tax hit from 2015 and beyond into 2013-14, where the tax is unlikely to come into play. If the Sox figure they'll pay the tax in two of the three years from 2015-17 (iirc, you get hosed if you're over the threshold three straight years, so they'll presumably get under once), then the tax savings would shave a couple million off the club's actual cost over the life of the contract. It's not a reason to do the deal in itself, but it moves the needle a little bit.
Also, it's worth mentioning that Pedroia has "only" earned $20mm for his career to date. Figure he pays nearly half of that in taxes and union dues, lives like a pro ballplayer, takes care of family members, and invests a couple million -- it's gone. I'm not suggesting you should cry for Pedroia by any means, but I could certainly understand if the opportunity to triple the guaranteed money he has coming his way (from $20mm to $60mm or so) and to pocket a $10mm signing bonus was enough to entice him to give up a theoretical payday after his age 31 season.
Edit: I think I'm right about the $12-15mm AAV on an extension, but I think the Sox have to go four or five years to get it done. Suppose Pedroia would extend for 5/60 -- do you do that?
Edited by maufman, 16 November 2012 - 07:31 PM.