Flaherty grew up in West Nyack, New York and graduated in 1985 from Saint Joseph Regional High School in Montvale, New Jersey. He went to grammar school at St. Anthony School in Nanuet, New York. He attended George Washington University, graduating in 1987 with a BA in Speech Communications and a minor in Psychology. He batted and threw right-handed.\n', '

Drafted by the Boston Red Sox in 1988, he moved through the farm system and broke through with the Sox in 1992. He also played for the Red Sox in 1993, and in 1994 he was traded to the Detroit Tigers for Rich Rowland. In 1996, Flaherty had a 27-game hitting streak. This ranks as the third-longest hitting streak of all time by a catcher, behind only Sandy Alomar, Jr.\'s 30-game streak and Benito Santiago\'s 34-game streak.\n', '

In 1996, the Tigers traded Flaherty to the San Diego Padres, along with Chris Gomez, for Brad Ausmus, Andújar Cedeño, and a minor leaguer. In 1997, the Padres traded Flaherty to the Tampa Bay Devil Rays for Andy Sheets and Brian Boehringer. He played as the Devil Rays\' everyday catcher through the 2002 season. As a member of the Devil Rays, he earned notoriety for breaking up a Pedro Martínez no-hitter in the ninth inning.\n', '

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