1901-1982. "Born in Baltimore and reared on the Eastern Shore, our 29th headmaster attended... Johns Hopkins, where he was an outstanding football and lacrosse player. Mr. Middleton then headed to Philadelphia to coach the varsity lacrosse team at Penn and teach at Episcopal Academy, where he also coached football and wrestling. He arrived at St. Paul's in 1944 determined to bolster the academic curriculum and win appropriate accreditation.... Mr. Middleton would... institute a grading system and standardized testing... and bring in key faculty members such as Martin Tullai, Thomas Longstreth, Jeanne Shreeve and Michael Rentko." (Crusader Connection, Issue 21, February 2016)