Steinbrenner aside, Cashman is typically good when allowed to do his thing. The Brosius deal was amazing, as well as picking up O'Neil and Tino when their stock was down somewhat. the Yankees have made their share of dumb moves though, and sometimes it's hard to tell what was Cashman and what was King George. I'd say it's a fairly even split with them on boners, though the obvious ones usually land with George (Irabu, Lofton etc.). He does have, even with KG, the biggest bankroll to work with though, and it's impossible to say how he'd do with a smaller market, say, half of what NY spends. My gut says he'd do well, helped by his experience in NY, but I can't be 100% sure. It's really a blessing/curse type thing in NY, and the fact that he looks eternally stressed out really doesn't shock me
Cashman wasn't GM when they traded for O'Neil.