He sued over a cloud contract he lost to Microsoft for so long that the contract was cancelled due to being technologically obsolete. ($10 billion)
He took NASA to the Government Accountability Office (GAO) over giving SpaceX the sole Human Landing System contract to land people on the moon as part of the Artemis Project (SpaceX was less than 1/2 the price with a massive cargo advantage and is already under development and has flown, whereas the competition only has mockups) and now that they ruled for SpaceX is taking it to court.
So yeah I'd say he sounds like a dick and that ignores all the stories out of Amazon.