In recent years, Graham Allison of Harvard Kennedy School has coined the phrase "Thucydides Trap" to refer to the risk of war when a rising power causes fear in an established power. In his 2015 article on The Atlantic and 2017 book, Prof. Allison expounded on the Thucydides Trap using some of the 16 case files from the last 500 years of world history that his team has compiled. However, no quantitative analysis was attempted. This presentation aims to drive the discussion deeper by quantifying the risk. Based on careful review of all 16 case files at https://www.belfercenter.org/thucydides-trap/case-file, time to event (war) data were gleaned. Different survival models were fitted. AIC based model averaging was utilized to derive some quantitative features of Thucydides Trap risk, which may provide some insights to the larger question of our historical time.