Tyga
You may know Tyga as a rapper, or you may know him as the ex-boyfriend of self-made “billionaire” Kylie Jenner. He has a current net worth estimate of around $5 million, but roughly eight years ago, during the peak of his rapping career, he found himself in quite a bit of financial trouble.
Apparently, he rented jewelry on credit and failed to pay the jeweler. Between 2015 and 2016, he found himself in more trouble after failing to pay rent to his landlords and causing irreparable damages to the estates. All of the luxury vehicles he purchased were repossessed due to, yet again, failure to pay.