Ouch! If his foot was for the most part still in that shoe, then I don't know how someone comes back from that after a month or so. I've been lucky not to have every sprained an ankle of nearly that magnitude. I've had a little twist here and there and once did a little damage to the inside of the ankle which is rare, when kicking a soccer ball while someone else was trying to kick the other side of that same ball at the same time.
Anyhow, once you stretch those ligaments they never shrink back to what they once were and the person is prone to stretch and sprain it again. I hope he heals up quickly.
As much as I like getting Ws against good teams, I like doing it against teams that are at full strength.