Background
From a Canadian mother, he was born in Preakness in what is now Wayne, New Jersey, where his American father Charles Stuart Littlefield (1833–1915), was employed by Milton Holbrook Sanford"s Preakness Stables. His father worked as a jockey in Toronto and is also an inductee of the Canadian Horse Racing Hall of Fame who won the first ever edition of the Queen"s Plate in 1860 and again in 1862 and as a trainer, won the 1885 Preakness Stakes.