Three econometric models were built between January and March 2020 to predict the September 3, 2020 General Election in Jamaica. These are the economics and security model (model1), the economics and security model with JLP leader acceptance (model 2), and the economics and security model with PNP leader acceptance (model 3). All three models accurately predicted a win for the Jamaica Labour Party. A Jack-knife resampling was performed for cross validation. These models show how the macro-economy, security concerns and party leader popularity influence election outcomes, with similar findings in the literature. However, there are peculiarities in the Anglophone Caribbean because the Jamaican voters respond to economic and security concerns in different ways than the voters in the global north. For example, increases in the debt to GDP ratio and the homicide rate predicted a JLP win. This work should be replicated in the Caribbean and Latin America using panel data.