Say what you want about a guy like Boras, but he ALWAYS seems to be maximizing what the player gets. As a fan that can be frustrating but in a way it's his (and his firm) job.
Which got me to wondering: I wonder if and/or how often an agent gets in trouble financially or a little cash strapped or sniffing retirement themselves and they push a player into a contract or extension that may not be in the absolute best interests of the player.
It could be hard to detect and may not ever be detected (in fact, in the case of injury it might actually work out to the benefit of the player).
For example let's say a player (I will use Chipper since he's retired) let's say CJ is in his first year of arby and his agent is going through a divorce and needs some cash to buy out the equity in the home he shares with his soon to be ex and he starts selling CJ on the idea of a contract extension with the Braves where CJ get's more guaranteed money (and a big signing bonus) but gives up earning potential through his arby years. Maybe the Braves weren't even thinking extension but fell into the happy occurrence.
It might actually be CJ giving up millions of dollars of potential earnings. But, his agent needed cash now and unless CJ (or others) was privy to that info, he may go along thinking he got a great deal. And, if he blew his knee out in year 2 of the deal and never played again, it would be.