The worst contracts in all the land

MLB Trade Rumor’s Tim Dierkes offered up some food for Spring Training thought this week as he ran down his list of the 45 worst contracts in baseball. Tim lists two current members of the Yanks’ 40-man roster and one guy DFA’d last year:

• Jorge Posada, Yankees. Four years, $52MM ($13MM per year). Signed November of 2007.
• Hideki Matsui, Yankees. Four years, $52MM ($13MM per year). Signed November of 2005.
• Kei Igawa, Yankees. Five years, $46MM ($9.2MM per year). Signed in December of ’06, this was a clear and poorly thought-out response to Boston’s Daisuke Matsuzaka signing.

If those are the worst contracts the Yanks have, we don’t have much to worry about. Sadly, though, I think Tim misses the mark. Let’s first dismiss these three contracts. Kei Igawa is a legitimately bad deal. The Yanks had a knee-jerk reaction to the Daisuke Matsuzaka signing and inked Igawa to a ill-fated four-year deal. Much of that, though, is the signing bonus, and Igawa costs the Yanks just $5 million in taxable expenditures. That’s not too bad a deal for a team with the Yanks’ deep pockets.

Jorge and Hideki present interesting case studies in contracts. Posada’s deal wasn’t bad and still has the potential to be good. While he is a 37-year-old catcher, he is coming off of some very stellar seasons at the plate. The deal became bad on a cold night in April when Posada threw out his shoulder. This injury had nothing to do with wear and tear behind the plate, and he should be able to come back as well as anyone his age could expect to. If Posada eventually becomes a full-time DH and hits as he has in the past, the deal still looks fine.

Hideki Matsui is good when healthy, but good health has eluded him lately. He missed much of 2006 with a shattered wrist and has since encountered knee problems. He’s in the final year of his deal and will DH. The Yanks would probably agree with the assessment here: The money could have been put to better use.

So what’s missing? Well, Fack Youk and I are on the same wavelength here. When I read this list 24 hours ago, I first thought, “Alex Rodriguez.” On Tuesday, Fack Youk wondered why the Yanks’ third baseman isn’t on the list. Jay rests his argument on PED use and the Scandal of 2009. I dissent.

Rather, A-Rod’s deal was bad from the day it was signed. Sure, from a business perspective, the Steinbrenners must have thought it would pay off. But from a baseball perspective, what team in its right mind would sign a 32-year-old to a ten-year deal worth as much as $300 million? While the deal is structured so that A-Rod earns just $21 million in 2015 and $20 million in both 2016 and 2017, no GM would ever sign a 40-year-old to a three-year, $61-million deal. This contract was bad before the PED problem; it’s just gotten worse.

In a similar vein is Derek Jeter’s deal. Jeter is owed $42 million over the next two seasons, and I’d say Jorge Posada is more likely to earn his money than Jeter is his. (This evaluation of Jeter’s deal may be unfair because the Yanks signed him to a ten-year extension knowing they would be overpaying him at the end. Perhaps this deal evens out in the long run.)

Finally, Ken Davidoff adds his two cents to this discussion. The Yankees, he writes, currently have $91 million in committed payroll for 2012. If CC Sabathia opts out as I expect him to do, that figure drops to a still-unreasonable $68 million. The Red Sox meanwhile are one of three teams with $0 owed to players in 2012.

While the Boston figure would have risen had they succeeded in signing Mark Teixeira this winter, Davidoff’s point is that the Yanks are limiting their future flexibility with some questionable deals. Less than one-sixth of the team will earn $91 million in 2012. How do you fill up a roster without zooming past that $200-$250 million level and still win?

The Yanks’ approach over the last eight years has always been spend, spend, spend. While the organization has tempered that spending with some player development, money remains king in the Bronx. If the Yanks don’t win over the next few seasons, the final years of these very long contracts won’t appear promising.