Troy Franklin O'Leary (born August 4, 1969) is an American former professional baseball outfielder who played with the Milwaukee Brewers (-), Boston Red Sox (-), Montreal Expos () and Chicago Cubs (). He batted and threw left-handed. In an 11-season career, O'Leary posted a .274 batting average with 127 home runs and 591 runs batted in in 1198 games. Career O'Leary attended Cypress High School in Cypress, California. He initially committed to play college football at Oregon State as a wide receiver. A 13th-round pick in , O'Leary enjoyed a great season at Double-A El Paso, winning the Texas League batting title with a .334 average and stealing 28 bases. O'Leary had batted over .330 twice before. He was promoted to Milwaukee a year later, and after two seasons, he was selected off waivers by the Red Sox. O'Leary hit his first career home run September 1, 1994 off San Diego Padres reliever Adam Clark. O'Leary hit .308 in his first season with the Boston Red Sox and was named the 1995 Red Sox Rookie of the Year. O'Leary collected at least 70 RBI from - and reached double digit home run totals in all 7 seasons with the Red Sox. Troy enjoyed the best year of his career statistically in 1999. He led the Red Sox with 28 home runs in the regular season, was second on the team to Nomar Garciaparra in RBI (103), and finished with a .280 batting average. He played in 157 of the 162 regular season games and finished with 596 at bats, leading the team in both categories. Troy also posted 84 runs (3rd on team), 167 hits (3rd on team), 36 doubles (4th on team), and a .495 slugging percentage (3rd on team). One of the greatest performances of O'Leary's career and in Boston Red Sox postseason history took place on October 11, 1999 in the decisive game 5 of the 1999 American League Division Series versus the Cleveland Indians. Boston entered the top half of the third inning trailing 5-2. With runners on second and third and first base open, Indians manager Mike Hargrove chose to intentionally walk Nomar Garciaparra, who had homered in the first inning, to load the bases for O'Leary. O'Leary responded by sending a Charles Nagy breaking ball 417 feet over the right field fence for the first grand slam in Red Sox post-season history, giving Boston