In gambling circles (in the UK at least) Phil would be classed 'vulnerable' and continuing to allow him to gamble while undergoing a bankruptcy would be in direct breach of a company's responsible gambling policy which could lead to massive fines or losing a gaming license altogether.
In gacha circles he's classed as a prestigious whale and allowed to continue to pump thousands upon thousands a month, unchecked, into a chance at a fancy new JPEG.
If he wasn't such a begging, manipulative, exceptional, deceitful, lying, toxic-manbaby fuckup I could feel sorry for him. Mobile game MTX stuff is incredibly predatory and you can't even win anything tangible. If I had to write a DSP redemption arc after his bankruptcy he'd come clean about how addicted he was and become an advocate for the regulation of some of this stuff. He would be in his element pity-splaining how he his 11 year pioneer lets-play legacy was left ruined at the hands of someone else and definitely not his own fault.