If any of this is at all interesting to you, I'd recommend checking out the very excellent ESPN documentary "Broke": http://www.espn.com/30for30/film?page=broke ESPN's 30 for 30 docs are really great, even if you're not particularly huge into sports. Broke is one of my favorites (after a "The Two Escobars"). It goes into a lot of detail about how ill-prepared many professional athletes are for the lifestyle, how they…
His advisor seemed like a good guy and talked about the dangers of family asking for money and hangers on. His advisor acted like the bad cop and actually did the rejections for requests and even introduced the player to other players who made good choices and could be a mentor/friend.
Outside the allowance if he wants a new car or vacation he calls the advisor and they tell him yes or no or later and help him get a good deal if yes.
He talked about having no financial clue early on and straight up didn't know the value of say $20k because he had never been exposed to dealing with money in that way.
He also talked about teammates blowing through their money like crazy and meanwhile he saves.
He did a stint in the NBA d league for rehab at one point and bought a not so great car (relative) because he thought having his usual car there would be embarrassing as it was quite a contrast relative to his d league teammates. Finally one of his teammates asked why he was driving that boring old car, so he had his car brought to the local city so his teammates could drive it ;)
Granted this guy has several houses, bought stuff for family and can spend like crazy on his allowance, but within some level of reason.
Dude was lucky he got a good advisor and was smart enough to listen.