None of that means Henry was fine with his overspending. In fact, all of that happened prio to the 2019 February announcement that DD would get extended. In fact, most of that happened before Henry announced on the field DD would get an extension.
However, since February, DD did extend Sale and Bogaerts. Those contracts, on top of numerous others, appear to have been a factor.
Of course, like many, I think that Henry and Co. might have tolerated all of that if they kept winning...