 If you liked
Gin to Kin
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 ...then you might like
Tobaku Mokushiroku Kaiji
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Protagonist that gets introduced to the underground, criminal side of the society, where his task is to make gambles that involve ridiculous sums of money. Both series have lot of well written mind games and Gin to Kin also feels a bit like Kaiji prototype, with not only the protagonist being similar, but also for example the prototype of Hyoudou can be observed.