Maybe if he'd tried harder, maybe if he had been stronger he could have stopped his mother from dying
Maybe if he had been a better son his father wouldn't have had so many reasons to hit him
Maybe if he had been a little more understanding he could have stopped Sammy from leaving home and abandoning him in Stanford
Maybe if he had been a better person he wouldn't have cracked under Alistair's pressure, he wouldn't have tortured so many souls
Maybe if he had been there, Sam wouldn't have started taking demon blood, he wouldn't have been with Ruby, he wouldn't have started the apocalypse
Maybe if he had been wiser, a better leader, Jo and Ellen would still be alive
Maybe if he had been less depraved, he wouldn't have fallen in love with Cas