Trade prospects, and maybe Joba Chamberlain or Phil Hughes to Toronto for Roy Halladay? Hang on to the youngsters, like Jesus Montero and Austin Jackson, and watch the Red Sox get the best pitcher available who is not already in a New York Yankee uniform?
That is the question confronting Yankee General Manager Brian Cashman this winter. Here is Jon Heyman of SI.com discussing the possibility.
Here is the most obvious reason the Yankees (or Red Sox) may now finally have a legit shot to trade for arguably baseball's best pitcher: New Toronto GM Alex Anthopoulos is making it clear he is genuinely willing to consider a deal with either the Yankees or Red Sox, a sharp contrast to Anthopoulos' predecessor, J.P. Ricciardi, who had GMs convinced he'd never make a Halladay trade with either the Yankees or Red Sox.
I have only one thing to say about this. MAKE THIS HAPPEN, CASH! If there is a realistic possibility you can put Halladay in pinstripes YOU HAVE TO DO THIS!!
If it costs you Montero, so be it. The Yankees are flush with catching prospects, and Montero might end up being just a DH, anyway.
If it costs you A-Jax, so be it. He might be a good big-league player some day. He might also be Ricky Ledee or Ruben Rivera. You don't pass on Roy Halladay to keep a guy who MIGHT become a good big-league outfielder.
If it costs you Joba Chamberlain, so be it. We still don't know what Joba is, but I think we know he is unlikely to become a Halladay-caliber starter. Besides, you would still have Phil Hughes, and I will bet you a buck (yeah, I'm a big gambler) that Hughes ends up having a better -- and longer -- career than Chamberlain.
If it costs you Hughes instead of Chamberlain, well, you still have Joba. And Ian Kennedy. And Dellin Betances. And you can always throw gazillions of dollars at Aroldis Chapman.
Want a list of reasons that are probably better, and most definitely funnier, than anything I can offer why the Yankees should do this? Diehard Yankee fan Jane Heller offers such a list over at Confessions of a She Fan. I'm not exactly jumping for joy like Jane at the thought of Halladay in pinstripes, but I do love the idea.