Connolly was born in Manchester, England, and played cricket as a boy. It was not until his family emigrated to the United States in 1885, settling in Natick, Massachusetts, that he saw the game of baseball played for the first time, but he was quickly fascinated and resolved himself to learning as much about the game as he could. He immersed himself in the rule book, and within a few years was umpiring for local games. While working in YMCA games, he was discovered by major league umpire Tim Hurst, who obtained a position for Connolly in the New England League, where he umpired from 1894 to 1897.\n', '

In 1898, the National League (NL) brought Connolly up to the majors, but he was angered by the league president\'s reluctance to back up umpires\' decisions on the field, and resigned in the middle of the 1900 season, then signed with the fledgling American League (AL) in 1901. That league\'s president, Ban Johnson, was eager to create a reputation for the AL as a solid challenger to the NL, and he gave umpires a greater measure of support than they had previously received, demonstrating that attacks upon umpires would not be tolerated and that their judgment was final. On April 24, 1901, Connolly had the privilege of umpiring, as its sole arbiter, the first AL game ever played.\n', '

Although he had begun his career by showing that he was willing to remove players from the field — he ejected more than 10 in his first AL season — he came to earn great respect from the players, and once went 5 full seasons (1925–1929) without ejecting a player.note He also showed an ability to stand firm against the toughest players in defense of the rules; on September 11, 1912, he called Ty Cobb out for stepping across home plate while batting, after Cobb had batted in a run during an attempted intentional walk. During the ensuing argument, Connolly was struck in the mouth by a bottle thrown by a spectator. His reputation earned him prominent game assignments, including the first AL games ever played at Comiskey Park, Shibe Park, Fenway Park, and Yankee Stadium. Connolly was also the sole AL umpire chosen to work in the first World Series in 1903.\n', '

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