Jon Heyman thinks Cash is the fifth best GM in baseball.
I would have put Cash 4th and Dombrowski 5th since Dombrowski has built his team the way the Yankees used to, signing free agents and trading the farm for stars.
Since Cashman took control of the organization after the 2005 season we've seen a focus on improving the farm by bidding over slot in the June draft and spending big on international signings.
His free agent pitching choices have been terrible, but I haven't seen anybody with a better track record on that count. Kevin Brown was doing well before he punching a frickin' wall; Javy Vazquez got run out of town. Randy Johnson's line the year before the Yankees' traded for him: 245.2 IP, 290K, 0.90 WHIP. Theo outbid Cash for Dice-K by nearly $20 million.
So now we build from within.
This year we'll see the roster flexibility that Cash has wanted reach the bullpen and the rotation. There's $80,000,000 coming off the books at the end of the season (Giambi, Pettitte, Abreu, Moose, Pavano, Farnsworth). There's finally poised to be a crop of free agents worth talking about (Teixeira, Burnett, Harden, Sabathia, K-Rod, Rafael Soriano).
I hope Cashman gets the chance to play with those resources.