Are the Yankees paid too well to win?

This is a guest post by Paul Vinelli.

After enduring another horrific start from Andy Pettitte (earning $16 million this season), a strange question enters my mind:

Are the Yankees’ players paid too well to win?

I’m not an economist, so my logic is almost entirely anecdotal. My formative years with the Yankees were the late 1980s and early 1990s. Back then, the team nearly always sported one of the largest payrolls in baseball. Steinbrenner and company signed “tough, proven” pitchers (Rick Rhoden, Andy Hawkins), over-hyped “stud prospects” (Hensley Meulens), platooned “aspiring sluggers” (Kevin Maas, Mike Blowers) and routinely overpaid one-dimensional outfielders (Deion Sanders, Jesse Barfield). It was a culture of meddling ownership, fiscal irresponsibility, reckless trades, and dismal grooming of young talent.

As a result, while growing up I always believed in the illusion that the Yankees could compete because the team could afford to swallow its most dreadful mistakes in supplementing the efforts of superstars like Mattingly, Henderson, Winfield, and Righetti. However, with the introduction of sabermetrics and the new generation of free-spending owners, I fear that the current squad fields too many mistake signings and that this affects overall performance.

While the current Yankees administration continues to overpay its players, the competition has become far savvier in how it allocates its resources. The Angels and Tigers have owners that are willing to spend money — and they do so relatively intelligently. The A’s have Billy Beane. The Mariners’ front office is clueless (witness the Bedard trade), yet their team still competes somehow. Cleveland has a bunch of young studs, and the Rays’ collection of prospects might be the best in baseball. Most terrifyingly, the Red Sox employ terrific scouting and top sabermetricians while wielding a payroll that rivals New York’s.

And what of the Yankees? Two years ago I considered the Mussina signing to be unwise ($22 million for 07-08) and in 2001 I was rabidly against bringing on Giambi (my friends and I deem the current championship drought as “the curse of the contract”). Andy Pettitte earns $16 million this year, though fortunately his deal is only for one year. Left field is entrusted to the immobile Matsui and the feeble-armed Damon ($26 million combined this year and next). Abreu was re-signed for a ghastly one-year sum, and his effort in RF is best categorized as “easy-going.” If Jorge isn’t splitting time between 1B and DH by the end of 2009, I’ll honestly be surprised. Carl Pavano – ’nuff said.

I believe that the Yankees have repeatedly tendered these ridiculous contracts in the past few years in order to give the elder Steinbrenner one last shot at the title. I respect this win now approach — however, the dynastic nucleus is aging (Pettitte, Jeter, Posada, Rivera) and there is a management struggle at the top (Hank vs. Hal vs. Cash vs. Levine). I’m not sure that if the team even wanted to make a big move (e.g. trade for Sabathia mid-season) that it even could foster the consensus to do so.

Hopefully when the current contracts expire the team will choose to focus on building from within instead of signing another big name to patrol left field. This might require a year or two of non-playoff growing pains, but I’m just hoping that 2008 won’t be one of those years.