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Around the Yankee Universe: Roy Halladay Edition

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I have been incredibly reluctant to jump into the Roy Halladay discussion. I still do it with trepidation, because I think his chances of winding up with the Yankees are nearly non-existent. Yet, a couple of respected Yankee writers have painted the scenario for how it 'could' happen, so I might as well.

Peter Abraham lays out the case for how the Yankees 'could' put Doc in pinstripes.

Here is what I will give up:

Joba Chamberlain. The unexplained loss of velocity is a concern. So is the stubborn unwillingness to listen to others. There is a chance he could be great. But as each day passes, there seems to be more of a chance that he won’t be. He has a great story, but maybe we’ve already seen the best part. Look at this way, what the odds he will be as good as Halladay will be for the rest of this season and next? Zero.

Jesus Montero. There has to be pain in this trade and this is it. Jesus of Venezuela might be the best power hitter in the minors and could be a difference-maker for any team. But he’s a catcher and that is the one position where the Yankees are loaded. The defensively refined Austin Romine is developmentally close to Montero and Francisco Cervelli could well prove to be an adequate stopgap. Plus the Yankees have a bunch of impressive young catchers in the pipeline including Kyle Higashioka, Gary Sanchez and (soon enough) J.R. Murphy. It’ll hurt, but Montero could well be a DH in five years. The world is full of DHs.

Anybody else: Yes, anybody else in the minors. Austin Jackson, Dellin Betances, Zack McAllister, take your pick. This is Roy Halladay, after all.

Sure, Halladay will add $7 million to the payroll this season. Big deal. The Yankees are drawing more fans than any team out there and inventing new revenue streams every day. Broadband access, Yankees Universe, etc. There must be $7 million in there somewhere. Check the Legends Seats for loose change.

Bill Madden of the Daily News lays out a similar scenario, but goes a step further. Madden says it is a move the Yankees 'should' make.

Let's assume none of the logical suspects steps forward with the kind of deal Ricciardi has to have to justify trading Halladay to the Toronto fans. It can be assumed that from the Yankees he would have to have either Phil Hughes or Joba Chamberlain and their top catching prospect, 19-year-old Jesus Montero, who was recently promoted to Double-A Trenton, and another top pitching prospect along the lines of a Mark Melancon or Zach McAllister.

Given that Cashman is fiercely protective of his farm system, he would undoubtedly gulp hard at that. But if Halladay ever should fall to him by default, he should not hesitate to give up any of his top prospects. Whatever it takes. We're talking about the ultimate difference-maker here in Halladay. And in the Yankees' quest to get to the World Series, their starting pitching is once again in question after CC Sabathia and A.J. Burnett. Cashman knows he can't count on Chien-Ming Wang to return to his old form any more than he can count on 37-year-old Andy Pettitte to have a second-half resurgence.

Between now and the trading deadline, Cashman is going to have to find another reliable starting pitcher. He appears to have the necessary chips to land the most reliable one out there. For him, it would be an unexpected do-over for not making the Santana deal. A lot still has to happen with other clubs for the Blue Jays to turn to the Yankees with Halladay. But if it does come to pass, Cashman shouldn't have to be reminded what he lost by not getting Santana when he had the chance.


Starting pitching, after all, is still the Yankees' Achilles heel. According to Baseball Prospectus, the Yankees have gotten quality starts in just 43% of their games, 12th in the 14-team American League. That isn't going to cut it if the Yankees are going to win the World Series in 2009.

And winning that 27th championship is what this season is all about, isn't it? The Yankees' window of opportunity with their current core is closing. Mariano Rivera, Derek Jeter, Johnny Damon, Alex Rodriguez and Jorge Posada are performing as well right now as they likely ever will again. Newly-minted Yankees CC Sabathia, Mark Teixeira and A.J. Burnett are in their primes.

It's been too long now since the Yankees paraded down the Canyon of Heroes. I know General Manager Brian Cashman has been protective of the Yankee youngsters, and I have lauded him for it. Maybe, though, just maybe now is the right time to strike.