Let's think like a young adult. If he wants his master's paid for, then I get that, could use it to his advantage. I guess it will depend on a lot of factors between he and his life goals.
Here is the thing I think everyone has to understand-- he is a grown man now. He isn't a kid, he isn't immature. Does he want to hang out with 18-year old freshmen?
Does he want to play hoops, get yelled at, have a curfew, watch what he eats and works out in a college environment?
What happens if he just wants some cash in his pocket and go on trip to the Caribbean and eat high-carb foods and drink beer?
I don't even know if he wants to play professionally.
On the flip side, you can never get college back. Pro aspirations? No idea how Europe has opened after Covid, he might not have those opportunities, might not have a job, and says life is good lets give it one more try.
But, sometimes people do have to move on.