Nothing and I mean nothing is ever straightforward with that Cluster A personality disorder fuckup. Everything is crouched into qualifications, annotated with asterisks or hiding a toxic source of shame.
Served honorably in the military but booted out for doing drugs
Won an NPC show because the competition (and himself) looked like absolute wet shit.
Worked at wall street but always at low level positions - fucked off at the first opportunity
Bought a big house but it was all with daddy's money.
Had a child with a woman but abused her and got a nice collection of mugshots in return.
And these are just the "successes", the outright failures are well documented.