Frank Drake
https://docs.google.com/document/d/1iz9fN24WoUBIt_gOFB6g8m12SFlxtlHfrFnMACHjulU/edit?usp=sharing
If you ask Frank Drake where his problems began...well, it'd probably begin with his useless asshole drunk of a dad, and the reason he had to take some loans out to save his mom and sis that quickly became favors for the Chicago Outfit when he couldn't expect to pay back and they decided he worked better as a smuggler than a stooge, that'd probably be a good answer.
But if you asked how he somehow ended up being traded over to the Bureau, it'd probably have to do with how he decided to volunteer for driving a big ol' suit named Faulke to evade some pursuers, and to keep a weird radio doohickey connected to all the way - 'discreet testing', they called it. Yeah, it was weird, but the payout meant he wouldn't have to work for the next three months, and they challenged his driving skills. Whattyagonnado?
Well, Faulke was impressed. Good as his word. And then suddenly revealed that this was a job interview, and those were trained CIA agents that were following him - and they ended up legitimately lost, all while the numbers station he was testing sung like a bluebird. So congrats, he was hired, and now he got to be a driver, transporter of 'delicate materials', and underworld contact for the Director - oh yeah, and aliens were real. Go figure.
At least he doesn't need to worry about his current bosses shooting at him because it was a bad day.