He took his first professional job in baseball for $40.00 a month, in 1901 as a pitcher for the Terre Haute Three-I League team. In his first season, he pitched thirty-one games and won twenty-three. He won twenty-seven out of forty-two games for Omaha in 1902. Because of his deformed pitching hand, Brown threw curve balls that were difficult to hit, and his maniacal sinker ball was punctuated by a fiendish dip. Reluctant batters had no choice but to swing at Brown's sinkers, very low to the ground as they were. Right-handed batters sent Brown's pitches down and out, and left-handed batters sent them down and in. Either way Brown's pitching more often than not allowed the fielding team led by Brown to clinch an easy out.
The St. Louis Cardinals purchased Brown from Omaha in 1903, bringing him into the National League (NL). With his career on track, he married Sallie Burgham that year. A lackluster 9-13 season sent him to the Chicago Cubs in 1904, as part of a double trade with Mike O'Neill. During his first season with the Cubs, he led the league with ten shutouts. In 1906 he finished the season 26-6, leading the league with nine shutouts and an earned run average (ERA) of 1.04.
Brown pitched for the Cubs for nine years. Between 1906 and 1910 he won 127 games, and in six separate seasons he won more than twenty games. With Brown on the mound the Cubs won the pennant four times: in 1906, 1907, 1908, and 1910. He pitched World Series shutout games in 1906, 1907, and 1908. In 1907 he pitched a no-hitter that won the series. From 1908-11, Brown led the league in saves.
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