I think Scar was always meant to win. He was so, so close to third life. It was up to pure skill that Grian landed more crits. So, in Last Life The Watchers took Grian away from the equation. He still lost.
Double Life. The Watchers realised he was stronger with allies, stronger with Grian at least. Alas, they couldn't force Grian to play his own game. And Scar died alone in the woods.
Limited Life. He had a family. The Waters decided to keep Grian at arms length, Scar's cousin. Scar's cousin who eventually killed him.
Secret Life. The Watchers were finally in the game. Even if it was just through a statue. Make Scar alone. Make him friendless. It wasn't a coincidence Grian wanted Scar to be allies on the fucking session Scar had to do the opposite of everything someone told him. They pushed him to his limits. Not only lonley and friendless, but hated, too.
Scar was always meant to win. It just took a while for The Watchers to figure out how