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In The Fast and the Furious: Tokyo Drift, we find that Han is in some sort of business with Yakuzas and is actively ripping them off (even befriended the Yakuza's nephew to gain their trust etc). He doesn't appear to be stealing very large sums of money though. Chronologically, Tokyo Drift takes place after Fast & Furious 6, which happens after Fast Five after which all of the team became filthy rich (enough to buy private jets, multiple lamborghinis and what not).

Further, in Tokyo Drift, Han himself claims and demonstrates that he has plenty of money. He can't be stealing significant enough amounts to be comparable to what he already has. He probably doesn't even need to be in business with the Yakuza anyway, since he has enough money to last more than a lifetime. Then why is he doing it and, more importantly, why is he stealing insignificant amounts? Just for fun?

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    Because the writers didn't know he was filthy rich when TD was made =) – BlueMoon93 Jan 5 '17 at 10:13
  • "..he has enough money to last more than a lifetime." That adds up to a lot of money, unless you're completely lacking in imagination. And even if you are lacking in imagination, there will be a slew of people hanging around to suggest things for you to buy. When someone complimented a member of the Onassis family on the soft, supple leather covering their sofa, the family member commented that it was the foreskins of sperm whales. That kind of luxury doesn't come cheap. – Andrew Thompson Jan 5 '17 at 11:33
  • @BlueMoon93 Yes, that probably is it. I keep wondering if they had the overall story (especially the exits of main characters) planned out well in advance....and that Sung Kang probably signed up for more a vision of than just Tokyo Drift, but probably the character worked well enough and got a much bigger role with Tokyo Drift retrofitting. – Achilles Jan 5 '17 at 12:13
  • @AndrewThompson My comment was based on how all of them seemed to retire and started living their dream lives at the end of Fast Five (it did portray the heist as the last job). So, we find everyone else flying around in their private jets and stuff except for Han who is still working to earn/steal money that is pretty insignificant in comparison to what he already has. – Achilles Jan 5 '17 at 12:19
  • Weren't two of the crew seen in a casino risking everything on the spin of a roulette wheel? People are different, and some do insane things when dumped with huge amounts of money. OTOH, some people don't know when enough is enough, and even when rich, seek further 'excitement'. Either possibility might explain why Han got into nefarious activities after that windfall, despite having at one moment, seemingly ridiculous amounts of money at his disposal. – Andrew Thompson Jan 5 '17 at 13:55
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Based on @BlueMoon93's comment, it would probably be safe to say that it can be attributed to Tokyo Drift being non-canon (partially anyway) and perhaps a mistake on writer's part in Fast & Furious 6 -

Han becomes rich after Fast Five which was released in 2011, Tokyo Drift had come out five years before in 2006. The film writers, at the time of writing Tokyo Drift, likely couldn't have known the turn the story would take half a decade in future and then the retrofitting of Tokyo Drift into the main story in Fast & Furious 6 failed to properly explain this particular bit.

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Why do people become "fast and furious"? It's not to break speed records. They're thrill seekers. They just happen to center their thrills (mostly) on fast cars, but they do get off on robbing people. They've shown that time and time again, from small gas trucks to the wealthiest person in an entire country.

Han was chasing the thrill of ripping off the most dangerous gang in Tokyo.

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I have also questioned Tokyo Drift many times as it seems like a lot of the story and characters roles (for example Morimoto) deserve a lot more explanation. But with this question I came to the conclusion that by the time that Han actually begins to live in Tokyo, he would’ve already spent quite a share of his money travelling and opening a garage. And yes, what about Giselles money after she died? Well she had probably spent quite a bit and knowing Han, he most likely gave the money she left behind to her family. And also, the business DK and Han have together may actually be more costly than it seems, as they drive cars and modify others cars with high end upgrades, and distribute most likely illegal items such as drugs through their drivers Sean and Morimoto, meaning that there is also money being spent on that and drugs worth selling when it’s people like Han and DK are most likely big amounts (as DK mentions late shipments). So the reason Han may be stealing is because it’s actually a lot more money than it seems for one, secondly, he knows DK will not notice on his own as he does not pay enough attention (seen when his uncle tells him Han stole), and lastly, it’s always important to have some source of income, even if you are rich.

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