Opinion: The Roy Halladay Situation
According to Joel Sherman of the New York Post, the Yankees remain bystanders rather than aggressive pursuers for Blue Jays RHP Roy Halladay.
The way I understand it – and I think this is what Sherman is essentially saying as well – the Yankees, Phillies and Red Sox, among other teams, would prefer to trade one or two 
top prospects to get Halladay, and then let him hit the free agent market, knowing they will get at least two top draft picks if he eventually signs elsewhere.
And so, I believe talk of a ‘hot pursuit from the Red Sox,’ as it was written earlier this week, is because Boston must have seen an opportunity to give up only one or two big-time pitching prospects in exchange for one season from Halladay, and so they were rushing to force Toronto to make a quick decision.
I mean, if Halladay doesn’t care, if he is only concerned with leaving Toronto and getting on to a team with a chance to win a World Series next season, then it’s open season, he can just sit back and wait to see which perennial contender gives up the best player to the Jays, such as, say, Joba Chamberlain from the Yankees, or Clay Buccholz from the Sox, or Kyle Drabeck from the Phillies, etc. However, if Halladay wants a big-time contract extension, then the entire storyline changes, since he holds all the cards.
In the Johan Santana Saga from 2006, interested teams had to essentially signal to the pitcher what he could expect from them in terms of a contract extension, as he signaled to the market place what he would require. Santana wanted to sign a long-term deal with the Mets, and, from what I was told, he said so much to the Twins early on, probably because he knew the Mets 
would dish the six-year extension, while the Yankees and Red Sox would not. And so, the Twins had no choice but to accept a collection of questionable prospects, or else no trade would be made.
And so, today, if a team wants Halladay for the next several seasons, at big money, they’re probably going to have to let him know through ‘backchannels,’ and then, based on that ‘hunch,’ Halladay can dictate to the Blue Jays where he will go. If the Blue Jays have no choice but to accept a basket of mid-level prospects, so be it, and they’ll then be forced to either do the deal, or do nothing, and instead be happy with draft pick compensation the following off season.
In the end, Sherman writes, “The Blue Jays have yet to divulge exactly what it would take to land Halladay.”
This makes sense, because, I bet, as of right now, no team is willing to give the 32–year-old Halladay a six-year extension like Santana got… and so, everyone, from inquiring teams to the Jays to Halladay, nobody knows yet what this trade and contract will need to look like.
Actually, I think that is what the Winter Meetings are for.
