Harry Flippin was widely considered in his day to be one of the South's finest all-around athletes. At EHS, he won letters in four sports-football, basketball, baseball, and track – yet still found time to serve as Head Monitor, President of the Fairfax Literary Society, Chairman of the Hop Committee, President of the Missionary Society, and as member or head of almost every other committee or activity the school offered.

On the football team, Mr. Flippin played tight end and was captain. In basketball, he was called the "all-around man" by the Whispers of 1926, and he was famous for his ability to broad jump from the foul line to the end zone, scoring during the leap-a roaring twenties version of Michael Jordan. In baseball, he hit home runs in eight games out of twelve, batting over .400. But in track, he was nothing short of phenomenal, setting school records in the 120-yard high hurdles in 1926 and also in the low hurdles, his times setting Virginia state records as well. He was undefeated in both the high and low hurdle events his last year at the High School. He was also awarded the Rinehart Medal for Athletic Worth and the Dulaney Award for the outstanding member of the track team.

A track star later at Virginia, he was the National Pentathlon Champion in 1927, and was All-American in track that same year. In the winter of 1929, he set the world's record for the 60-yard indoor high hurdles. Phi Beta Kappa at Virginia, he was captain of the track team in 1929 and turned down major league baseball offers to become a physician.

Over 100 of his patients and friends donated the funds to build Flippin Field House; it was dedicated in his honor in 1967. Mr. Flippin died in 1968.