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Hmmmmm can it be slightly earlier? I got some ideas for some 20th century stuff–

Edward: He’d work at a speakeasy place in Florida–bootlegging booze all the way from Cuba. Although he would try to make sure that Bacardi Rum becomes widespread in the US, and try to make sure that the Prohibition repeal gets passed in order to do this. He’d also be the type to wana give out his disposable income to anyone and everyone he meets on the street, always carrying around a fat wad of cash with him just to shoo everyone away with money.

Adéwalé: He’d originally be part of the Irish-British-Italian-Jewish-’coloreds’ crime syndicate of New York/New Jersey/Chicago/Los Angeles/Las Vegas/Florida, but along the line he’d get tired of the criminal life and instead join Haytham’s nightclub as an employee. He’d be a bar tender or a waiter, but wants no part of the actual bootleg operation.

Ezio: Would be part of said crime syndicate and work for the infamous Lucky Luciano, Al Capone, Johnny Torio, and the like. Gotta have that Italian mafia, yes? He’d own an Italian restaurant but use it as a meeting at night for the Italian mob–also he sells booze at his restaurant. He’d also meet up with Al in Chicago from time to time and spend some uhhh…lovely time at that cat house that Al Capone does some bouncer work at. 😛

Haytham: He’d be a dirty, retired politician that owns a jazz nightclub. It caters specifically to Whites, but would have a majority of Black employees. In reality, he’s using the club as a front to sell booze under Prohibition.

Aveline: Would work at said nightclub as a singer, but has absolutely no part in the criminal activities. Sure she’ll drink every now and then, but has no connection to the crime syndicate.

Connor: He’d be the kid that tried to go to an Ivy League university or something but struggle with it, and also get into a lot of trouble with the drinking and boozing thanks to his bootlegging dad and gramps. Like I’m just trying to imagine 19/20-something year-old Connor trying to throw a booze party with other students for the first time, just to fit in and be as cool as possible. Instead, he gets in trouble with the law and his smooth talker of a politician dad tries to get him out of it. This would inspire him to study law later on and wants no part in any of the criminal activities of his family.

Shay: Also would be a ‘prohee’ agent at first, but would quit later on after unsuccessfully trying to reveal the Kenway’s (barring Connor) criminal operations–and instead land himself in the middle of the crime syndicate itself, unwillingly working for mob bosses like Al Capone and co.

Hmm…I think I’ve been watching a little too much of Boardwalk Empire….I blame my friend @its-sarah-bridget for this and the whole sexy Kenways-in-suits thing for kickstarting this brilliant AU we have mwahaha~

– Signore Ezio