Take the poster child for "classic bad pitching contract," Barry Zito. 7 years, 126 million. He's in the final year of it now, and earning less in terms of AAV than Buehrle and Santana. But he was signed a year earlier, and got locked into 2006 salaries and projections instead of 2008 or 2012 salaries and projections. It should go without sayin but those things tend to go up pretty fast in baseball. Which is why I think this aversion to long-term contracts is overblown. Even if your guy turns into a Zito, a team can still be a consistent contender as the Giants have shown. I like the longitudinal approach here but I think you should compare how much the guys who have been piecemealed onto contracts over that span have earned and produced, as compared to the guys who were locked up to big deals early. Carlos Silva earned 45 million between 2 separate 2-year contracts after leaving the Twins while posting a 6.77 ERA in under 200 innings. Nowhere near as bad as Zito's in retrospect. Heck, even Meche managed to post two 200+ inning seasons of sub-4 ERA ball in his 5-year, 55 million/deal. A bad contract but hardly an albatross in 2012 money, the final year of his deal. *edited for clarity