Just a thought... (possible Fallout 4 companion storyline spoilers)
Porter Gage has been around. He grew up as a settler, moved on to being a caravan guard and a scavver before becoming a raider. He must be in his early forties.
What if…what if he got a girl pregnant at 17? Gage doesn’t like getting wet. He has a wry sense of humour. He likes his loot. Keeps things at a distance (like not being the Overboss himself). He’s not a big man. Cleverer than he lets on even though he can’t read. Does this sound familiar?
Maybe the girl couldn’t cope with the baby and found some settlement willing to take it in. Just maybe her last name was…
MacCready. He doesn’t like getting wet, has a wry sense of humour, tends to keep things (and people) at a distance and likes his caps. He never knew his parents. He’s on the small side, for a man. Despite appearances, he’s a bright spark, well read too.