His father, a professional cricket player, moved his family to the United States after Harry's birth. By the time he was twenty, Wright, following his father's model, was playing for the Saint George Cricket Club in Hoboken, New Jersey, but he enjoyed playing baseball as well, and in 1858, he joined the Hoboken Knickerbockers baseball team, playing the outfield.

Played exclusively by amateurs until after the Civil War,

baseball had a reputation as a gentleman's sport, and it was very popular. Professional gamblers were quick to see betting opportunities, and they frequently arranged for skilled players in their employ to play for teams that attracted betting action. Amateur baseball was already becoming a money sport.

After the war Harry Wright