This is not something you can fix. Really.
You have three choices: live with it, stop playing with him, or ask him to get therapy-- and I'm not being facetious about that. Since the player knows he is causing problems, but is incapable of changing his behavior, there's no way you can force him to change. Maybe he has a real life phobia about being bankrupt, maybe he's got a mild case of OCD, who knows. Whatever it is, if he cannot change his behavior by wanting to, there is absolutely no way you can force that to happen.
On the other hand, if he's capable of change but unwilling to shape up, that means he's just being a jerk. Jerks don't require therapy, as they can often be cured by high-velocity application of an ordinary masonry brick. (Okay, now I'm being facetious. Slightly.