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But the answer to #1 is influenced by PR. If you instead asked "Would the Blue Jays trade Roy Halladay for a $19-million player who's being paid the minimum?" the answer would be yes.
But for many other teams in the same boat - that is, they have a highly-paid, excellent ballplayer on their roster, but they either need to cut costs, or they realize that they are not winning anything next year - they would gladly trade Halladay aware for 19 million dollars. Kansas City would. So would Detroit. If Tampa Bay, which probably has a payroll similar to Toronto, had Halladay left for one year, and then he told them that he was walking away, I have little doubt that they would sell Halladay for 19 million dollars. They would then turn that money into locking in their younger talent (Crawford, Zobrist, Garza, Shields, whomever), and perhaps their other soon-to-be-free agents (Pena and Crawford)into long-term, team-friendlier deals. In fact, I think most teams would take $19 million for one year of Roy Halladay, unless they honestly thought he was the difference in winning it all in 2010.
One last point. I love fangraphs, but if they really calculate that Halladay was worth $33 million last year, then it is a vacuum that has nothing to do with the current payroll structure of baseball. Nobody makes $33 million a year, even ARod, and nobody but the Yankees would ever pay $33 million for a baseball player in 2009. The impact any player - even the greatest players in the game - would have on the team's ability to construct a 25-man roster, especially given the luxury tax threshhold, makes that figure completely out of context with MLB in 2009.
Economics 101 - in a free market, how much is a baseball player worth?
Whatever somebody will pay him. Nobody will pay Halladay $33 million for his best career year. In fact, a big part of what makes this discussion interesting is that Halladay is currently making a salary that probably isn't too far off of what his current market value is. He's making almost $16 million in 2010 - any team getting him is not getting a deal (nor are they getting screwed). If he signed a FA contract this winter, he'd probably have an AAV of between $18m and $21m, right?
Compare this to Victor Martinez, whom the Red Sox acquired for 1 1/2 years - not one year - and is paying about $3m for the rest of his 2009 salary, and $7.1 m for his 2010 salary. Most would agree that they got a large percentage discount over what his market value would be if Martinez had been a FA in July 2009. That the Red Sox only gave up Masterson, Hagadone, and a minor-leaguer for this is remarkable, and goes back to my original point: I'm not seeing much recent evidence that a $16m in 2010, 33-year-old stud starter with one year left on his contract, no matter how good he is, is likely to fetch the kind of prospects Toronto hopes...unless they take on a similar amount of 2010 contract in return.
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