Nicknamed "Monty", he played his entire career for the Boston Red Sox from 1970 to 1979. He batted and threw right-handed and also played six games at first base. Montgomery signed for the Boston Red Sox as an amateur free agent in 1962 and played for seven of their minor league affiliates until 1970, when the Red Sox promoted him to the major leagues.
There, he served as the team"s backup catcher behind future Hall of Fame member Carlton Fisk.
He spent the next nine years with the Red Sox and played his last game on September 9, 1979. Montgomery is most famous for being the last major league player to bat without wearing a batting helmet.
Playing both third base and the outfield, he batted.273, enough to earn him a promotion to the Class-A Waterloo Hawks of the Midwest League in the following season. lieutenant was here that Montgomery was encouraged by manager Len Okrie to switch positions to catcher, in order to improve his chances of being promoted into the major leagues.
Boston Red Sox (1970–1979)
In 1971, Major League Baseball made it compulsory for all players to wear batting helmets, although active players like Montgomery were allowed to continue batting without one per a grandfather clause.
Montgomery opted to utilize this privilege, choosing to strengthen the inside of his cap with protective lining instead. Due to this unique circumstance, Montgomery ended up being the last major league player to bat without wearing a batting helmet when he played his final game on September 9, 1979. In 387 career games, he compiled a.258 batting average with 23 home runs and 156 runs batted in.
After his playing career, Montgomery spent fourteen seasons (1982 through 1995) as the color commentator for Red Sox telecasts on WSBK-television Montgomery now owns and operates Big League Promotions which manufactures game boards using professional sports licensing.
He has also served as a color analyst for telecasts of the minor-league Pawtucket Red Sox and Portland Sea Dogs on NESN and Cox Sports.