Kelly, a robust 6-footer, became an umpire because of his weak hitting and proneness to injuries. He worked in both the NL and American Association in 1884 and was requested by the owners of the and Union Association Maroons when they agreed to play a seven-game series at the end of the season. The following year he was selected to umpire the “world championship” series between Chicago of the NL and St. Louis of the AA. In 1887 he managed the Louisville Eclipse of the AA, where he introduced the “Hurrah Plan” with the players sprinting to and from their positions, even in practice. At the end of the season, he umpired his third world championship series. Eventually, he was dismissed from umpiring as “unjustly severe.” He turned first to refereeing boxing and worked three championship bouts. He later opened a gambling house in New York.