Ray Montgomery (baseball) Raymond James Montgomery is an American professional baseball player and executive. He played in Major League Baseball during three seasons for the Houston Astros . He is the scouting director for the Milwaukee Brewers of MLB.Playing career Montgomery attended Archbishop Stepinac High School in White Plains, New York , and Fordham University . In 1989, he played collegiate summer baseball with the Chatham A's of the Cape Cod Baseball League . The Houston Astros selected Montgomery in the 13th round of the 1990 amateur draft . Montgomery played his first professional season with their Class A Auburn Astros in 1990, and his last with the New York Mets' Triple-A Norfolk Tides in 2001 . One of Ray Montgomery's career highlights came on July 24 , 1996, against the San Diego Padres when he hit a walk off home run as a pinch hitter in the tenth inning to give the Astros the win, 6-4. The home run , hit off San Diego's Ron Villone , was the first major league home run for the rookie.Executive career After his playing career, he spent four years as an area scout for the Milwaukee Brewers, during which time Milwaukee selected second baseman Rickie Weeks out of his South Texas/Louisiana territory. He was the Brewers' Midwest supervisor for two years and their assistant scouting director and national supervisor the next two years. In 2009, Montgomery turned down an offer to become the scouting director of the San Diego Padres because he had just moved to Connecticut and didn't want to relocate. In 2010, the Arizona Diamondbacks named Montgomery their new scouting director. He served four years in that role, until he returned to the Brewers as their scouting director in November 2014 .
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