Inspired by recent thoughts of Steve Phillips (not the philandering former-ESPN baseball analyst, rather the philandering former GM of the New York Mets) and his unhealthy past obsession with Mo Vaughn and his contract, I started to think about current "bad paper" contracts in the MLB, and after some research I can confirm that horribly-structured contracts do exist.
Now, what follows is not what you would call an "objective" ranking of bad contracts. Sure, statistics might be given to illustrate just how little a certain player's production correlates with his salary, but there are very few (if any) objective qualifiers for this list of bad MLB paper (except for money, duh).
However, one aspect that was scrutinized was contract length: there are no players on this list who have contracts ending either in 2010 or 2011 (This stipulation was added once I realized how many huge one- and two-year deals there are in the MLB). Also, appearing next to each player's name will be their age in 2010 and the rest of the money left on their contract, assuming all options are picked up/exercised/vested as well as no-trade clauses (appearing as "Full NT" or "Limited NT").
So which players are not living up to contracts whose overall worth rivals the GDP of many developing nations? Which players will be getting paid ridiculous amounts of money when they are closer to age 40 than they are their "prime-aged" years? These questions will (hopefully) be answered in due time, but for now just sit back, relax, and strap it down (read: NOT on) for a look at some ludicrously awful MLB paper.