Bills don't stop coming, but if you're a highly paid athlete then your money from your playing career should set you up for life. Divorce/child support is one thing, but if you have let's say $50mil in your account after you retire then you should be straight. A lot of these athletes don't pay attention to their yearly expenses.
Yeah, there's well to do ppl who retire with a couple million dollars and live a top tier lifestyle. Traveling, new houses etc
If you retire with 50 mil you should be able to live an insanely great life and still be nowhere near broke.