Annie arrived at the Henry Vilas Zoo as a gift from Alfred Ringling in 1918, seven years after the opening of the zoo. Thereafter she was kept as a single elephant until her death in 1948. She was replaced two years later with an elephant purchased and named Winky.
In October 1966, the Henry Vilas Zoo received an elephant from Morgan Berry to replace one sent to him several months prior. The new elephant was named Winkie II, named after her predecessor. Her namesake was dismissed from the zoo after she pulled a young child into her exhibit and killed her.
In 2000, the Henry Vilas Zoo made the decision to close their elephant exhibit and relocate their two elephants, Winkie and Penny, upon recommendation by the United States Department of Agriculture that the exhibit either be improved or elephants removed. Winkie was retired to Carol Buckley's private facility and Penny was transferred to the Riverbanks Zoo newly renovated $4 million exhibit for African elephants. She was temorarily housed at the Columbus Zoo with two other elephants slated for arrival at the South Carolina zoo.