[member="Vahn Fett"]
James; if he made different choices. Ah there are so many:
--If he hadn't fallen in love with and married Leighlah, she never would have died, he wouldn't be a playboy billioinare and a secret widower. He would have fallen in love with someone else and married them. He wouldn't be jumping from woman to woman to hide his fear of intimacy. He never would have left [member="Sasha Voss"].
--If he never would have done his deal with Kylo Kyr'am he would still be poor. And I mean "I only own this ship and a few dozen creds in my pocket" poor. It started a series of business ventures for him that made him the budding business Tycoon he is today; and purveyor of business deals and helping others get deals.
--If he never would have opened the Angel Den, he never would have gotten into the Crime Lord business of Soceras, he never would have become vested in land and making Dal'Bor his crime town.
--If he never would have formed the deal with [member="Solan Charr"] for being the fleeter of the COR, then he never would have turned Justice Shipping into an actual fleet. It would have remained a loose conglomerate of smugglers, privateers, and mercenaries.
--If he never was tortured by [member="Thraxis"], if [member="Rose Blade"] would have never fallen to the darkside, and if [member="Ryn'Dhal"] would have never been captured and tortured (all at once), he never would have fallen to the darkside for a stint. He would have remained the "I mean well, I just do bad things" guy. He went from "Space Robin hood" to "Space Punisher/Space Robin Hood"
--If [member="Lady Kay"] hadn't called him out for being like [member="Thraxis"] during his rescue stint for Ryn'Dhal, he would have fallen completely to the darkside, never to return. He would have continued to get worse, he would have begun to whole-sale butcher bad guys, people he perceived bad, and the like.
--If he would have been discovered by the Jedi early on instead of being raised by his Dad on a junk freighter who called them "Misguided saber jockeying Sorcerers" (A term James uses too), the he would be Jedi Master Justice, valor of peace instead of Jamas Justice the People's Criminal.
--If his dad wouldn't have been gunned down right in front of him, James would be working under his pa (unless his dad drank or smoked himself to death at this point). If his dad would have let James go with his mother when his mother left instead of keeping him and raising him, James would have been a bartender instead of a spacer, and he would have never even existed!
There are a lot of moments he could have changed. Moments that if they had been different, he would be very different. He could be happily married, or the next Darth, or Ren, or whatever they call Sith these days, or even a Jedi Master Consular. He could have become a psychotic cold-blooded killer, or he could have become the head of the Red Cross. So many options.