You would be hard-pressed to imagine someone worse off than the Toronto Blue Jays fan base in the aftermath of the Roy Halladay trade to the Philadelphia Phillies, but there is. Just follow that loud wailing and moaning sound, and you'll wind up at the New York offices of the Major League Baseball Players Association.

According to Joe Sheenan of Baseball Prospectus, the only remarkable aspect of this deal is that Halladay "took somewhere between 35-50 percent of his market value to facilitate a trade, leaving somewhere between $60 and $100 million in guaranteed money on the table".

Last season, C.C. Sabathia received a $161-million (all figures U.S.) from the New York Yankees as a free agent and two seasons before that Johan Santana orchestrated a trade to the New York Mets who renegotiated his contract to the tune of nearly $140-million over six-years. By our fair market calculations a chunk of money was left in the Brinks trucks.

Wow, talk about your new team discount! There are hundreds of baseball players and agents - as this is being typed - removing Halladay from their Christmas card lists.

Halladay's contract is so far removed from his market value that it looks like an error. Remember, he had to approve not only the contract, but the trade to the Phillies that precipitated it. He made the choice that he wanted to be with the Phillies so much—and wanted to be with them immediately so much—that it was worth it to him to leave $60 million, $80 million, maybe $100 million unclaimed. There is no way anyone could have predicted this even a few weeks ago. This is the kind of decision that a player gets to make for himself and his family. Halladay gets to play for a contender in 2010 and gets to do so with a team he wishes to play for, one that holds spring training near his Florida home, and he valued those things more than the marginal dollars foregone by not testing the market. I don't judge him for it, but I do think we should all be stunned by how much money this man left on the table. There is no precedent for it in sports.

Sure, the Halladay deal was like a was punch to the stomach for loyal Blue Jays fans, however, does anyone believe this deal gets done if "Doc" Halladay's agent is Scott Boras? Not bloody likely.

Of Unselfish Decisions and Restocked Systems [Baseball Prospectus]