I'd say trading Cliff Lee AND CC Sabathia for essentially nothing ALONE constitutes a bad track record.
Hafner, Grady and Lee were traded for right around a decade ago. Does the front office get a 10 year benefit of the doubt bump for those? What's the cut off for total amount of years before we're allowed to not trust a front office that hasn't pulled an impact player out of a trade for a decade?
Hafner, Lee and Grady were obviously part of fantastic trades. But frankly, it's been too long since they happened and there's been so many more misses than hits with player transactions since that time, that I'm gonna need some kind of parameters for when a front office can stop resting on their laurels before I'm allowed to say they suck.
Masterson, Choo and Asdrubal all fit into the same category...above average guys (most of the time) who nobody would ever dream of calling impact players.
Santana I'm willing to be optimistic with, especially because they landed him for Casey Blake.
Other than that...sorry...if they can't pull ANY impact players out of the trades they've made, they have a bad track record.