coming up with extended leon kennedy family lore is so fun. i've gone all in on the italian-american crime family aspect, and gave him an older sister who i'm now deeply attached to.
his original last name was marino, he only changed it to kennedy alongside his sister after their parents were killed in attempts to distance themsleves from their mafia connections. leon was raised in both jersey and NYC (he has SUCH city slicker vibes), moving to the city proper with his family when he was 10 and his parents deemed him old enough to understand not to snitch as they started teaching him the ropes. his mother ran a jewelry shop that was a front for her fence business (hence his familiarity with valuable gems in re4) and his father was a capo and particularly close with the consigliere leonardo, whom leon was named for.
after his parents are killed in a hit following his father trying to expose the underboss as a traitor to the don when leon is 14, his 20 year old sister rita leaves cornell where she's studying to become an environmental scientist in order to raise him. rita does her best to give him stability away from their parent's world, but leon overcorrects when trying to find a way to cope with his life being upturned and starts rebelling (common 14 year old L). he goes to parties, gets a tattoo, and bleaches his hair, but rita has quite literally been there, done that, and so reacts with empathy and care. considering rita is an anarchocommunist, leon starts clinging to authority HARD to define himself in opposition to both his parents and his sister, which is what leads him down the path of becoming a cop.
this successfully drives a wedge between rita and leon, and he doesn't speak to her for his entire academy stint after he moves out. during that time rita loses her ecologist job and joins an earth liberation front cell after traveling abroad in europe and being inspired to join the cause, becoming more radicalized against authority in the face of her brother's betrayal. they speak once just before leon leaves for raccoon city, having a huge fight over rita planning an arson (i was inspired by the vail ski resort burning here, the costliest eco-terrorist action ever undertaken in the US) with her E.L.F. cell and leon being a cop. rita doesn't learn he's alive until a week after the bombing when leon calls her burner, desperate for help with sherry, and tells her everything about umbrella. he's whisked away by his government shadows before they can meet up, and she doesn't hear anything from her brother for a year and a half, so she assumes the worst.
rita thinks umbrella killed her brother, so she goes scorched earth against them, bouncing around the world on a sabatoge campaign that makes her earlier arson appear like child's play and galvanizing her entire organization as well as anyone concerned about B.O.W. usage into taking action against umbrella. she writes a manifesto and founds R.A.I.N. (the radical action and investigative network. can you tell leon got his sense of humor from his sis?) specifically to target umbrella through direct action, corporate espionage and investigative journalism done by private citizens. it's decentralized and popular among survivors of raccoon city.
umbrella isn't happy with her and orders a hit on her cell, killing many of her friends in a nightclub, though she survives by the skin of her teeth. she rebuilds, becomes more violent in her destruction of umbrella, and R.A.I.N. takes on a life of its own, as the government labels her a terrorist twice over in the wake of R.A.I.N.'s escalating tactics and rising prominence in the public eye.
leon is able to make contact soon after and tries to get her to stop, to no avail. they aren't able to meet up until after operation javier, and the shell of a man she finds in place of her baby brother makes her turn her sights fully on the united states government. surely this has no repercussions for leon.