Trying to make a big splash in free agency automatically risks making a big mistake. While this winter's shopping season has been especially strange because of the overall economy, it's interesting that most teams haven't made the mistake of offering too many long-term contracts for pitchers. This is a reflection of the increasing certainty that anything beyond three years can quickly go from million-dollar expense to millstone on the payroll. Nevertheless, spend some teams did, and regrets they will most certainly have, but who did the worst?
Let's break this into different categories: the worst one-year, two-year, and three-year contracts, with honorable mentions in each category, capped by the worst deal of the winter for its length, expense, and likely return.