Michael Rosenberg of the Detroit Free Press lets us know why the Toronto GM absolutely must trade Halladay now:
What happens if the trade deadline passes and Roy Halladay is still a Blue Jay?
This is what you need to know about Halladay: right now, he has more value to the teams that are trying to trade for him than he does to the Blue Jays. Significantly more.
Consider: the Blue Jays owe Halladay roughly $20.45 million between now and the end of the 2010 season. But since they are sure to miss the playoffs this year, they are basically paying him for one potential pennant race, next year, in a division with the Red Sox, Yankees and Rays. That is a huge chunk of money for one starting pitcher in one pennant race.
And if the Blue Jays don't contend next year, then what? Halladay won't come out and say it, but he'll be out of there. He will have pitched 12 seasons in Toronto without throwing a postseason pitch. Why would he sign on for any more? Halladay's reluctance to sign an extension is presumably what fueled these trade talks in the first place.
The Blue Jays could then try to deal him by next summer's deadline, but the haul would be significantly smaller than it would be now, because he would be a two-month rental instead of a season-and-two-months rental.
The teams that are pursuing Halladay, on the other hand, are all contenders. They believe they will have him for two pennant races, minimum. And unlike Toronto, those teams are in prime position to sign Halladay to an extension, because they are contenders.
But right now, with Halladay in the middle of the best season of his career, coming off two straight dominant starts ... well, right now there is a perception that he is hands-down the best pitcher in the game. And that is the right time to trade him. It is the definition of peak value. (Even Halladay's birthday slightly inflates his current value — he is 31, but he turns 32 next month).
I agree with Rosenberg that the real question is "can the Blue Jays contend next year?". I say that is highly unlikely, their red hot start notwithstanding, so they need to move him at peak value, which obviously is now. Riccardi's self imposed deadline is nonsense, the Blue Jays can and possibly should wait as long as they can and then take the best offer before the calendar shows August.