Post Аниме characters who are frequently broke despite coming across large sums of money.

Sven Vollfied, from "Black Cat", who works as a bounty hunter.

Tsunade (Naruto)

u see.......she bet all her money on the gambling and loose everything....flat broke..and u know what happen Далее she will loan the money from the money lenders and bet on gambling and get broke again..........now she ia flat broke with a huuuuuuuuuuuuuge debt to her money lenders.............she also get a nick name in the field of Gambling............."The Legendary Sucker"......even after this she still going with the same routine she havent changed 1bit.....she have debt in all countries..........sooooo now the money lenders are chasing after her..........he he he he

Gintoki Sakata from GIntama

~Being a Jack of all trades he sometimes comes across jobs which pays alot... but after getting paid, he looses it all playing pachinko in a mad attempt to double it XD

The gang from Cowboy Bebop. If I recall they get like this quite often