Background
Gildersleeve was born on September 17, 1886 in Gildersleeve, Connecticut.
Gildersleeve was born on September 17, 1886 in Gildersleeve, Connecticut.
He graduated from Middletown High School in 1903, and attended college at Wesleyan University, where he played baseball and football. He graduated with a Bachelor of Surgery in 1908.
He served as the head coach at the New Hampshire College of Agriculture and the Mechanic Arts, Massachusetts Agricultural College, and Westminster College. The Meriden Daily Record called him a "star" athlete at Wesleyan. He then undertook postgraduate studies at Harvard University Summer School of physical training from 1909 to 1910.
Gildersleeve served as the "physical director" at Saint Lawrence University during that same time.
He coached at New Hampshire in 1909 and amassed a 3–4 record. Gildersleeve coached UMass in 1910 and amassed a 1–6–2 record.
He then coached Westminster in 1911 and amassed a 2–4–1 record. On October 7, 1911, he was arrested after a brawl erupted during the game against Pittsburgh.
The Pittsburgh Gazette Times criticized the law enforcement response in the incident:
"The arrest of Gildersleeve appeared ridiculous, in that he was the only one of the crowd taken by the police.
He is a small man and two big policmen grabbed him and took him across the field in full view of the crowd. The police acted as though Gildersleeve was a desperate criminal. This act failed to make a hit with the crowd, who were inclined to poke fun at the police for their brave acting"
He also coached baseball at the school.
In 1917, he coached baseball at Hyannis High School, and in his one season tenure, guided the team to the Cape Cod High School Championship.