Outlaws

Sawyer & Jack Via Christian Shephard

Sawyer and Dr. Christian Shephard meet at a bar in Sydney where they share a bottle of whiskey and Christian shares his story about the trouble between him and his son, though he never mentions his son's name.

Back on the island, Sawyer realized he'd met Jack's dad when Jack quoted his father's fateful saying, "That's why the Red Sox will never win the damn series." (Irony: the Sox did win the series shortly after the plane crashed)
Update:  Since the airing of The Glass Ballerina in season 3, Jack now knows the Red Sox did indeed win the World Series, to his utter amazement.