In late October and early November of 2003, the Sun unleashed a powerful series of events known as the Halloween storms. The coronal mass ejections launched by the Sun produced several severe compressions of the magnetosphere that moved the magnetopause inside of geosynchronous orbit. Such events are of interest to satellite operators, and the ability to predict magnetopause crossings along a given orbit is an important space weather capability. In this paper we compare geosynchronous observations of magnetopause crossings during the Halloween storms to crossings determined from the Lyon-Fedder-Mobarry global magnetohydrodynamic simulation of the magnetosphere as well to predictions of several empirical models of the magnetopause position. We calculate basic statistical information about the predictions as well as several standard skill scores. We find that the current Lyon-Fedder-Mobarry simulation of the storm provides a slightly better prediction of the magnetopause position than the empirical models we examined for the extreme conditions present in this study. While this is not surprising, given that conditions during the Halloween storms were well outside the parameter space of the empirical models, it does point out the need for physics-based models that can predict the effects of the most extreme events that are of significant interest to users of space weather forecasts.