Milano was a football player and wrestler at the school. He currently holds both the all-time single season rushing record (1,678 yards) and the all-time career rushing record (3,248 yards).

In wrestling, Milano holds the overall career best record of 127-15. He also holds the best single season record of 37-1. He went on to the University of Michigan, where he received a scholarship to wrestle for the Wolverines. As a sophomore, he decided to pursue his dream to play football for the Michigan Wolverines.