Brian Cashman has been around long enough to know what kind of pressure there is to win in New York and how high the standards are for the Yankees. However realistic or unrealistic it may be for those standards to be met, ownership always toes the company line of "our goal is to win a championship" and a lot of fans and media storylines fall in line with that statement. That's what happens when you've won 27 of them and been the biggest and most successful franchise in Major League Baseball for a hundred years.
Measured against those standards, the 4+ seasons since the last title have been increasingly disappointing. The Yankees have fallen further from the top of the American League in each season since 2009, culminating in a missed postseason last year and a battle to stay above .500 this year despite spending almost half a billion dollars in free agent reinforcements this past offseason. Cash has taken a good share of heat for this season's results, both of the fair (not finding a real backup first baseman, not spending more to build a better bench) and unfair (the McCann signing, the length of the Ellsbury deal, giving Beltran the 3rd year) varieties.
I'd grade him out at somewhere around a C+/B- myself, but if we're looking at just the few moves he's made this month, you have to be fair and give the guy credit for what he's done.
Taking names and stats and history out of the equation, simply consider the value he's given up compared to the value he's gotten back. He turned an almost 27-year-old, soft-tossing lefty who was signed to a MiL deal in 2011, was never considered a big time prospect, and was pitching incredibly poorly into a proven veteran right-hander with a track record of success pitching in the American League. He turned a non-roster invitee to Spring Training and an A-ball pitcher who's realistic ceiling is probably middle reliever into a switch-hitting third baseman in his prime who registers as an above-average defender by most metrics, has shown the ability to hit for good average, decent power, and get on base when healthy, and was an MVP candidate as recently as 2012. That's pretty damn good.
Consider also the fact that the 2 players Cash traded for are both in the final years of their contracts, so he's not taking on extra risk in terms of years or dollars owed. The 2 partner teams in these trades even agreed to take on some of the remaining salaries of the players they were trading away, approximately 36.7% of the total amount owed to them according to reports. So that's 2 players added to address positions of great need, very little given up for them in terms of internal assets, and a very small remaining monetary commitment to each of them. When you know you're dealing in the realm of "marginal upgrades", what more could you ask for?
The best thing about these deals might be that Cash was able to pull them off without the media getting wind of them. Maybe I'm misremembering, but I seem to recall the Yanks being linked to guys well before they ended up trading for them. Not this time. We didn't hear about the Chase Headley deal until it was already in the stages of being finalized despite Cash saying he had been working on it for weeks. The Brandon McCarthy trade came together very quickly and was finalized almost as soon as the initial reports started coming out. That's good GM'ing.
Cash wrapped up his session with the press on Tuesday by saying "I have more work to do", and I'm looking forward to seeing what that work will result in much more than I was at the beginning of the month. He said his preference was to add another hitter and there are hitters out there who would be good fits, but can Cash find another scenario that's as favorable to him and the Yankees as these last 2 have been? We'll soon find out. Say what you want about the job he did in the offseason, but don't say Cash hasn't been on his A-game when it's come to the trade market this year.