This is just another ridiculous fan post.

How do you guarantee he’s going to hit the market though? There’s always a chance someone can come in with a package and take him away, while signing him to an extension.

How many contenders (which is the only teams he’d ocnsider) have the talent to package for him however… is relatively unknown, but I’m sure Toronto would want some sort of prospect package, rather than losing him to FA.

http://www.nydailynews.com/sports/baseball/yankees/2009/11/12/2009-11-12_roy_halladay.html

A few interesting quotes:

If the Blue Jays keep Halladay but struggle, they could still move him at the trade deadline. They would surely get more for Halladay by trading him this winter, but according to the source, Beeston believes that would send the wrong message to the fan base entering 2010.

Halladay wants out of Toronto, but it’s unlikely that he would waive his no-trade clause to be dealt to a team unless he was able to sign a long-term extension – something only a select few teams have the resources to do, most notably the Yankees and Red Sox.

Others are wary of signing Lackey to a big contract, according to one Yankees executive, citing the righthander’s injury issues over the past two seasons. There is also the Angels’ apparent willingness to let him walk, which some see as a sign that they know something about the health of his arm that others don’t.

Seems to me like Halladay has a say in his trade and probably (I would guess) would rather be traded to a playoff contending team like the Sox or Yankees rather than some middle tier team that might give the Jays a bunch of prospects but gives him less of a chance at winning a division or pennant or WS.

The last quote is interesting because it highlights some potential issues as to why the Yankees might be hesitant to sign Lackey, regardless of his performance last year.

I’d say sell the farm for Halladay because he’s got a few upsides over every other starter out there:

1. He can make AJ better (AJ says Halladay is his mentor)
2. He can be a 3rd consistent quality starter with CC and Andy
3. He can make any of our younger starters better (if we keep Joba and/or Hughes)
4. If nothing else, he can continue to scare the crap out of the Red Sox instead of joining their ranks

Of course, we would all like to get Halladay for just money, even if we have to wait until the next offseason, but the reality is Cashman and/or the front office might not be willing to risk him going to the Red Sox if he can help our rotation in more ways than just being a good starter (or excellent starter). I’ve never seen any of our prospects play, but I’ve read many places that pitching and/or hitting in the minors is a world of difference from playing at the MLB level. Obviously our scouts and team execs and coaches know more than we do, so we can only hope they make the right decision and it doesn’t come back to bite us, especially in a playoff situation.

and again. This has a multiplier effect when you think of all the others he will affect. He said Rivera showed him how to throw a cutter at the AS game, imagine him with the pitching staff discussing the craft with MO, CC, Pettite, AJ,… with the others standing around.