His father, John Wesley Bennett (1837–1920), was a lawyer in Chicago who had served as a lieutenant colonel in the Army of the Potomac during the American Civil War.

[2][3][4] He was the captain of the 1898 team that won the school's first Western Conference championship with an undefeated and tie-free record of 10–0.

[4] At the time of his election as the Michigan team captain, the Detroit Free Press wrote: "Bennett is a Michigan player through and through, and his rise to his present position of prominence in football circles came by steady, hard work.

During these years, he supervised the construction of the St. Regis and Algonquin Hotels in New York and a factory for Bailey Banks and Biddle, jewelers, in Philadelphia.

In that position, he advised the city on engineering matters arising out of the water department's $10 million annual budget.

He was a major in the Quartermaster Corps and supervised the construction of a supply base in Brooklyn, New York.

He was survived by his son John Connable Bennett, who was serving in the U.S. Army Air Forces at the time.