RE: Earned $61 Million Playing In The NBA - Now Has Only $3,000 In The Bank
It's the same reason why people are taught only certain types of investing strategies, if they're taught any at all. As far as sports leagues go they love it when players spend too much, which is why they never discouraged the culture of overspending and flashy lifestyles amongst players (tons of peer pressure and keeping up with each other) because it's free advertising for the leagues if they're seen balling out and it makes sure the players have to keep signing new contracts for income even if their bodies are breaking down.
Otherwise players would always have the option of signing maybe 1 lucrative contract and then deciding what they wanted to do after or pursue the second contract with more bargaining power if the league knew they didn't need the money, instead of being financially obligated to take whatever is offered.
Employers love when employees are in rough financial spots because it increases their bargaining power. Regular people would do well to know that as a collective whole.
You're right, the teams could do more to help the players, but they don't view it as a long-term partnership, they most often just view the players and talent to be used. It doesn't matter what happens to each person who plays, what matters is the game. More often then not, I feel that the teams don't care about the players at all. That just means the players need to get smart and help themselves and each other out.