Mr. O'Keefe defeated Miss Rawles, Mr. Hartwig, and Mr. Gerrety on his way to the first Teacher Madness championship. O'Keefe set the gold standard for competitors in the tournament as he breezed through each round. Mr. O'Keefe would turn out to be golden for another reason as he was awarded the Golden Apple Award later in the year. 

In 2022, Mr. O'Keefe was named a Knight to Remember, solidifying his position as a Central Catholic icon.