We had a guy like that in my county named Lennie. He eventually acquired the nickname "Almost honest Lennie" because he always had some scam going that was just about, but not quite legal, and he knew it.
He had to do a UA (urine sample) for the courts once, and it had to be an observed sample where the officer stood by him to actually watch the urine exit his penis in order to maintain chain of custody. Lennie was so old, (around 72 then) and so messed up from meth, opioids, and lots of drinking, that the officer observing said when Lennie stood at the urinal after saying he was ready, while trying to get his penis out, he was late, and pissed his pants. All Lennie said was "AWWW, DAMNIT, can I try again in a couple of minutes, I'll go sit in the lobby." He was told NO, don't sit in the lobby, go sit outside...Looked a lot like the guy posted in this thread...just 40 years older.