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Born in Rural Retreat, Virginia to Andrew Phillippe and Jane Margaret Hackler, Phillippe first appeared in pro baseball with the National League's Louisville Colonels in 1899. He had a 21-17 record that year, which was highlighted by a no-hitter in just his seventh career game.
The Colonels disbanded after the season, before which owner Barney Dreyfuss shrewdly moved a number of Louisville players, including Phillippe, to the Pirates, a team Dreyfuss co-owned. Phillippe won 20 games for four straight seasons as the Pirates won three straight National League titles between 1901 and 1903.
Phillippe had the honor of starting the first World Series game for the Pirates against the Boston Americans in 1903. In a complete game victory, Phillippe struck out 10 batters and earned the win against Cy Young to start the best-of-9 series. He single-handedly guided the Pirates to a 3-1 series lead, earning the wins in each game, but when his arm wore down due to overuse, the Americans came back to win the series 5 games to 3, with Phillippe losing the last two. His five decisions in the World Series are still a record for a pitcher and one which will almost certainly never be equalled or broken.
He missed half of 1904 due to a sore arm, before winning 20 for a 6th time in 1905. His years as an ace ended in 1908, when he suffered from another sore arm and missed nearly the entire season.
Phillippe returned in 1909 to play a bit role on a Pirate team which went 110-42. In 1910, he was primarily used as a relief pitcher and had a 14-2 record. He retired after the 1911 season after making only 3 appearances that year.
Phillippe was widely renowned for his control. No pitcher who has debuted since 1893 (when the pitching mound was moved to its present distance of 60 feet and 6 inches away from home plate) has averaged fewer walks per nine innings than Phillippe.
Deacon is a distant relative of actor Ryan Phillippe, who named his first son Deacon in honor of the pitcher in 2003.