There's a very thin space between a decent season and a total washout, which is where the Yankees are living right now. It's pretty hard to disagree with your scathing assessment of Cashman; to have that size of a budget and to be this non-competitive has to fall on his shoulders. I mean it's one thing if your superstars like Judge are struggling, but with Calhoun and Cordero, you know what you're getting. Expecting them to suddenly change their spots and become consistently productive contributors is flat out weird.
I had no trouble watching Benintendi walk. What the White Sox are paying him is excessive IMO, even though at this point, his contract isn't a total bust, but the current parade of jurrassic Yankee hacks- Hicks, Donaldson, IKF, Cordero, Calhoun- that's an indication of a deliberate system of roster-building that makes the rest of the NL East extremely happy, (and has for years).
Very few GM's have the luxury of doing so little with so much and hanging on to their jobs. As the song goes, "nice work if you can get it."