Wasn't Abreu a salary dump by the Phils? That's another area where Cashman has a distinct advantage...the ability to take on big salaries and cash in on other teams' dumps, where sometimes he's the only bidder, as no one else wants to take on that player's contract.
I don't think we'll ever see it, but I'd like to see what Cashman would do with a mid-market payroll, where the top-tier free agents aren't always available to him, and he isn't free to spend as much as he wants.
The Abreu trade was partially a salary dump/partially a re-stock of the farm for the Phillies. At the time CJ Henry was a legitimate prospect that was regarded well. The Phillies originally wanted Phil Hughes but Cashman was able to hold them off. I know Hughes will go down as a disappointment in NY but he was a key part of the 2009 team out of the bullpen. The Yankees don't draft well but Cashman has been able to turn flawed prospects into useful pieces, sometimes in salary dumps, sometimes in outright theft like the Swisher trade.
I'm surprised Cashman never left to become a president of an organization with full control in a mid-market. I wouldn't be shocked if he wanted to but the Yankees just paid him too well not to leave.