1942 - Ann Dunham 

Jake (32) has long since lost any control or jurisdiction over Hitler, or any interest in controlling him for that matter. He's practically abandoned his post at Skaianet in terms of managing assets, and though remains figurehead of company, he's out exploring and adventuring, completely oblivious to whatever's going on in Europe. He hops from site to site, looking for Sburbian ruins to plunder. While on one such expedition in Kansas, he has an illegitimate daughter named Ann Harley. He takes custody of her, apprentices her as an adventurer, and takes her all over the place on his adventures. He brings her to Hawaii as he explores the Pacific, to look for a fabled island he's discovered some lore about. But as a teen, she finally ditches him there, and changes her name to Ann Dunham (her mother's name), because she's sick of her douchebag dad. Years later, she gives birth to Barack Obama.