After the death of his father, Rum Rogers Jr. inherited the run-down cottage that he owned. He soon became irritated at the number of treasure seekers who kept turning up asking to find out about the lost treasure of Big Whoop that his father had famously found.
Two months after inheriting the cottage, Guybrush Threepwood arrived at his door. When Threepwood challenged Rogers to a sword fight, Rogers responded by saying that sword fights were for "wimps, weenies and sissies" and instead proposed a drinking contest.
He competed frequently in such contests, using his own "contest grog", which was his fathers recipe. It had double the alcohol and calories of normal grog and was so powerful that it almost instantly knocked out anyone who drank it. Threepwood was able to win the contest by replacing his contest grog with some Near-Grog, a non-alcoholic substitute, leaving Rum Rogers Jr. passed out on the floor.