In 1916, EHS needed a teacher, maybe one who could coach a little baseball; P.H. Callaway needed a job. Thus began one of the greatest combinations in the history of education, as the star baseball player from the University of Virginia began what would be, in addition to over 70 years of teaching in the classroom, more than 50 years of coaching, advising, and keeping score for the EHS baseball team.
He developed some great teams and great players, one of whom, Edmund P.W. "Jelly" Richardson, lost only one game in three years of pitching for the High School. For the rest of his life, until age and infirmity made it impossible, Richardson returned to Episcopal the Friday before the Woodberry game to throw batting practice for his beloved coach, Mr. Callaway.
The tradition of the head coach wearing a uniform of his team was ignored by Mr. Callaway, who always wore his old University of Virginia baseball uniform, allowing one more boy to suit up for EHS. Many of his baseball records at the University of Virginia still stand, among them his having struck out the opposing team once with nine consecutive strikes. Legend has it that the longest home run was hit off a pitch of Mr. Callaway's; the ball had to have been thrown hard.