The Will Rogers phenomenon describes when elements are moved or migrate from one set to another and the averages in both sets increase. We provide a mathematical condition for when the phenomenon occurs and when sequential migration results in the phenomenon occurring at each step of migration. We use an example to explore other questions including the likelihood of the phenomenon occurring and its relationship to Simpson's paradox. This work is joint with Allison Mocny (undergraduate student at Case Western University) and Jennifer Wilson (New School University).