United Launch Alliance has been awarded probably a couple of orders of magnitude more than that over the past two decades, yet the difference in technology advancement rate with SpaceX is staggering (and don't get me started about the bottomless pit of stupidity that is/was Roscosmos). I would say that the "CIA buddy" thing cannot possibly be the only explanation.

I cannot comment about Gwynne Shotwell; I lack the corresponding knowledge. I can only note that if Elon Musk is a completely mediocre person, he still must be doing something right because the world is full of mediocre people who achieve much less than he has, and I don't believe in blind luck.