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There were some gags like Kondou's fake sword etc. that were derived from real life rumors.
I want to know how much data we actually have about the real life counterparts of the characters in Gintama.
Are any of their personality traits known to historians?
How closely do the characters in the anime resemble them?
How about the historical accuracy of the Shinsengumi command structure?
And the Joi and Minawarigumi?

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Don't know that much so I'll just contribute a bit.

Gintama really doesn't stay that true; it's more like taking bits from each real life character's known traits and either using that as inspiration or warping them into something vastly different. As far as Shinsengumi hierarchy, it is loyal- Hijikata was also known as the Demon Vice Commander, Kondo was commander & close with Hijikata, Sougo (Souji) was 1st unit captain. Shinpachi's real life counterpart, however, was part of the Shinsengumi and he obviously is not in Gintama (although he does don the uniform in several occasions xP).

A little other tidbit: Sougo died of tuberculosis pretty early and he had a sister who outlived him, but that was inverted:

with Mitsuba dying instead.

Also, Takasugi definitely had a deep bond with Shoyo-sensei's real life counterpart, Shoin, and grieved a lot after Shoin's beheading.

The Mimawarigumi was also considered to be elite, so that part was kept.

..I may come back to add more if I think of anything else.

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