Time and results will prove whether his efforts and focus works these days or not. He's not a player's coach, and he's not organization friendly. Most GM/Coach positions do not work these days, as roles are so specialized. See Bill OBrien and Doc Rivers as recent examples. Gruden has his fingerprints over every move, and their focus has been on putting together a team of football playing jessies. The problem is, the big question mark draft picks have proven to be questionable and not genius more oft than not. The Jessies can't stay on the field.
But you're not wrong on exercising options and realizing greatest value of assets. New England has done it for years. Seattle does a great job of it. Colts suck and have been injury plagued, but they don't do a bad job. Most in depth analysis has shown how crazy difficult it is to win a championship these days when position X makes Y% of yearly cap. BUT, those other places continue to be FA destinations. Because of the ownership, coaching staff, and administrations. They are mostly known as being upfront with their athletes, and they run solid programs so that when players leave they are often still wanted and can often cash in elsewhere. The raiders are not a free agent destination. They ride rookie contracts and veteran rehab projects.
The Raiders are a joke, in recent history they are one of thee most futile professional sports teams by an extremely large number of measurements. It was not long ago where it was a great game if we scored a touchdown, and early season hopes were that you won a game or two by season's end. Carr is a face of the franchise who represents the grueling endurance to the play the right way for a loser. He's a bit more than capable of starting, we're talking previously league MVP status, and when given even half a cupboard can go toe to toe with the Rogers' and Mahomes'.
Mariota was talked up 10x bigger than Carr, given the biggest backup contract there is, gets injured, and Carr is trying to ball out. Given Chucky's history with large contract players, as well as the usually not great breakup that happens (which then generates stories of discontent, which can lower player value), to put his name on the franchise by taking advantage of Carr's value and trading at the end of the year would be disasterous. We are not New England, every year isn't championship or bust, Chucky doesn't have any relevant (read recent) success - we are not in a position to sacrifice or f**k over the guy that has led us out of the dark ages.
(Maybe I'm just salty that in a year where my top running back was Doug Martin in the last year of his career and my top wide receivers were Jordy Nelson (also in his last year), Marcell Ateman, and Seth Roberts, they couldn't even just leave Janikowski and Marquette King on the team for fun)