kiryu to his fellow gangsters right at the beginning of yakuza 1: oh yeah i actually went completely nuts on the real estate in this city a while ago. yeah like i bought a lot of buildings
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in reply to @Willow's post:
he really does canonically make tens of millions of yen by the end of each game and then lose it before the next one huh
He swallowed the cash in order to fight good
the fact several buildings appear to have closed between yakuza 0 and 1 means kiryu's business ventures either fail by the time he leaves prison (either due to mismanagement or the fact kiryu is not there to solve their issues) or he actually sold those buildings for a lucrative profit