Oliver also had health problems, such as pyorrhea, a gum disease that was partly caused by his love of sugar sandwiches and it made it very difficult for him to play and he soon began delegating solos to younger players, but by 1935, he could no longer play the trumpet at all. Oliver was stranded in Savannah, Georgia, where he pawned his trumpet and finest suits and briefly ran a fruit stall, then he worked as a janitor at Wimberly's Recreation Hall (526-528 West Broad Street).