When Oceanic 815 crashed on the island in Season 1, I always thought that if only Sawyer had been a little less "Every man for himself" in his attitude, he would have been a better leader than Jack.
As Sawyer notes in Season 5, Jack never thought things through. He merely reacted, and got people killed.
He repeatedly led people on one wild goose chase after another. Up to the radio tower. Down to the beach. Into the caves. Onto the ship. Round and round. Chasing their tails.
In this episode, Sawyer confirms my suspicion. He always had a cooler head than Jack.