Assuming of course that he really has won. However, even the math accounts for that possibility. There is an .03% chance he really did win as much as he has claimed. So, no math violation whatsoever. Now, if you really believe that someone is that lucky for 10 straight years I have some prime Wyoming ocean front property available ...
No, the results do not differ from the math. The math is not tied to optimal play as you appear to think. The math applies to any strategy a player uses. It simply shifts the bell curve to the left.
All a bell curve does in VP is provide a range of possible outcomes and the associated probabilities of a method of play. There is not a single bell curve.