Im shocked jay owe's so much money considering he is really good at making it.
I used to work in debt collections and would come across celebrities accounts. 95% of the time the debt is usually something where the celeb took the account out in their name for someone else and forgot it was even out there when they and that person went separate ways.
For example, T.I. might owe AT&T like $2000 because he bought his boys phones in like '07 and while they were in his entourage he was taking care of the bill because they rolled with him. Let's say he goes to jail and does his stint and his crew disappears; when he gets out he's not even remembering that bill and a.ssumes his folks took care of it when all they did was just get rid of the phones and let the accounts go into collections, especially since it wasn't in their name.
A lot of cats out there have stuff and don't really realize it, especially athletes. I might have even ran across Brock Lesnar for a phone bill once or twice. It's impossible to actually get ahold of him, so he probably doesn't even know