Buster Olney’s advice to Brian Cashman: ask your coaches and talent evaluators whether Joba and Phil will be big starters or shutdown relievers one day, then:
And if the smart people that Cashman trusts believe that Hughes and/or Chamberlain will be anything other than (A) dominant closers, or (B) No. 2-type AL East starters, well, then I’d call Toronto immediately and be ready to talk about trading one or perhaps even both of the young pitchers.
That’s fine as far as it goes, but the real deal breaker is probably not Joba and/or Hughes — them vs. Halladay is a classic bird in the hand decision — but whether or not to include someone like catching prospect Jesus Montero, who the Blue Jays will be asking for if they have any brains.
I understand the impulse to want to make this such a cut-and-dried decision on the Yankees’ part, but these kinds of deals are gambles, even for New York.