Chapman soon hired a former restaurant manageress named Bessie Taylor to work at the pub, and a relationship soon blossomed. Another bogus marriage was entered into, and again Chapman began to abuse his "wife." According to Elizabeth Painter, Chapman "shouted and threw things at Bessie and on one occasion threatened her with a revolver."
Interestingly enough, Bessie began suffering from the same disease as her predecessor, and to avoid controversy, Chapman left the Prince of Wales and left for The Grapes in Bishop's Stortford. After an operation, her condition remained poor, and the two moved back to London.
Chapman leased the Monument Tavern in the Borough, were she grew steadily worse. She was to die, just like her predecessor, on what should have been a joyous holiday: Valentine's Day, 1901. Cause of death this time was said to have been "exhaustion from vomiting and diarrhoea."
Mrs. Painter visited her friend almost every day during her illness, and was more than once the butt of many a cold joke from George Chapman. On more than one occasion, when she would enter the house and inquire as to Bessie's health, Chapman would reply, "Your friend is dead." Painter would run upstairs, already grieving the loss, only to find her still alive in the bed. When Mrs. Painter visited on the 15th, Chapman told her that Bessie was "much about the same." To her indignation, Mrs. Painter later learned she had died the previous day.
Of interest at this time is the fact that Chapman had attempted to commit arson on the Monument Tavern, which was quickly losing its lease, around this time.