Several lines of evidence suggest that the Milky Way underwent a major merger at z ∼ 2 with the Gaia-Sausage-Enceladus (GSE) galaxy. Here we use H3 Survey data to argue that GSE entered the Galaxy on a retrograde orbit based on a population of highly retrograde stars with chemistry similar to the largely radial GSE debris. We present the first tailored N-body simulations of the merger. From a grid of ≈500 simulations we find that a GSE with M ∗ = 5 × 108 M o˙, M DM = 2 × 1011 M o˙ best matches the H3 data. This simulation shows that the retrograde stars are stripped from GSE's outer disk early in the merger. Despite being selected purely on angular momenta and radial distributions, this simulation reproduces and explains the following pheno...