For all that Cashman may have brought, because he has done some good, I'd still take Theo. As Bosox said, outside of Cano and a few others, he hasn't done a hell of a lot. Let's definitely make a nice list of funny names: Jaret Wright, Carl Pavano, Randy Johnson.
That's enough for me. 10's of millions of dollars for almost no production (Randy Johnson maybe a bit more than the others). It's a simplistic point, but you get the idea. Cashman and NY have been the kings of big, big money deals that quite often fall flat.