During the battle for Sugar Loaf Hill, when he was the only survivor, that is why he got the silver medal. Roy's not in jail because of police cover up/corruption. They defended Cole at the funeral because if they didn't, it makes all cops look bad. Phelps was shot because of killing the innocent women & children. That's also why all his comrades hated him. Not sure why he cheated, but perhaps the developers didn't have enough time to flesh the story out and dig a bit deeper. In some ways, Cole was not very likable, but I admired him, if only because he was human, and very flawed, but he tried to do the right thing (most of the time).