I suppose the thing I find most depressing is that it doesn't seem to have affected his career in any meaningful way.

The longer I live, the more that seeing other people fail upwards saddens me. As Ben Franklin said of a particular dude:

On the whole I then wondered much how such a man came to be entrusted with so important a business as the conduct of a great army, but having since seen more of the great world, and its means of obtaining and motives for giving places, my wonder is diminished.