No doubt, and I think JR's 'hit man' narrative was born in prison (possibly to appear tougher than he is/was). However, it doesn't appear that JR tried to capitalize off his prison connections after release. Career criminals usually can't hold down a job, they're too entitled and mixed up in the criminal underworld. Always looking for the next scam, opportunity. If I had to guess, I'd say JR had a hard time in prison emotionally. I think he saw how much life he missed out on while locked away.
JR had no problem working hard for an honest day's pay. Not to say he wouldn't take a bonus from CWW, I'm just pointing out that he didn't appear to take an illegal shortcut for money right after prison like some felons do, he sought and maintained a normal, labor intensive job. Illegal acts certainly pay more for less work. And IIRC, there was talk of JR receiving training in irons works? Or something like that, welding? He was learning a trade, bettering himself, trying to move away from the label of FELON, criminal, troubled kid.
And completely JMO, and entirely irrelevant but I couldn't help notice how JR was the most dressed up at CWW's wedding. A sign of respect, not only to CWW but for himself, his future self maybe? JR mentioned to his employers about how his 'brother' was going to buy him a new wardrobe. Super strange thing to say and lie about. If he was truly expecting clothes (from CWW or MS:thinking
and was excited, isn't that a little bit sad?