The ledger does not care how much sleep you get. It's all about WAR and money, and when you flick the abacus it says that deal was a complete abomination.
In hindsight, AA probably learned a lot from it, and the Dickey trade. The point isn't that these trades "defined his tenure" it's just that they played significantly into his objective record when Shapiro made the unpopular decision to part ways with him.
Like, when he left Toronto he had a mixed track record. He made some brilliant moves and put together good and exciting teams for two runs, but he also had some huge fumble trades and the organization's farm system + MLB situation was a bit ugly (s***** farm, old expensive players)