Bob Montgomery was from Nashville, Tennesee and signed as an amateur free agent with the Red Sox in 1962 after playing several sports for Central High School, where he was all-state in three sports. For Central's baseball team, he pitched, played first base, and played outfield.

Bob first played professionally for the Olean, New York, team in the Red Sox farm system. There he played outfield and third base and batted .273, earning him a step up in the system in 1963. He next went to Waterloo, Iowa, where he was turned into a catcher and even made the league’s All-Star team.

Monty continued to rise in the system, if slowly, and by 1969 was playing for Triple-A Louisville. In 1970 he put in another year at Triple-A and earned himself a call-up to the big-league club once Louisville’s season was over.

Monty made his major-league debut, subbing for catcher Tom Satriano and took over as the regular catcher for the rest of the season. He saw a lot of action in September, playing in 22 games and performing reasonably well.

Duane Josephson was acquired over the winter to be the regular catcher, but a series of nagging injuries provided plenty of opportunities for Monty to share the catching in 1971.

When Carlton Fisk was called up in September, he would take center stage starting in 1972 and Monty, understandably, played the backup, taking full advantage of the at-bats he had.

In 1973, Monty hit .320 as the backup, but when Fisk suffered a season-ending injury in June 1974, he stepped in with Tim Blackwell serving as his backup.

Fisk was still unable to return as the 1975 season opened, due to a broken arm suffered in spring training and Monty was the main man again. At the season’s start, he was responsible for the game-winning RBI in four of the first 11 wins. When Fisk came back in June, he got injured again and was out when he hurt his finger in August. So Monty got quite a bit of playing time in September.

In postseason play, Monty saw no action at all in the three-game ALCS victory over Oakland, and almost missed out on any action in the World Series. He finally got his chance appearing as a pinch-hitter in the bottom of the ninth inning in Game #7. He grounded out to short and Yaz flew out to center to end the Series.

With Fisk healthy the full year in 1976, Monty got into only 31 games and got even less playing time in 1977. 1978 was another exceptional Red Sox season and Fisk played in almost every game, so Monty saw action in only ten games. He had just seven hits in 29 at-bats and more than half of those hits all came in one game, the second game of a doubleheader at Tiger Stadium. He was 4-for-5 with an RBI triple in the ninth inning.

1979 was the last year for Monty as a major-league ballplayer. He appeared in 32 games and chalked up a career-best .349 BA in 86 at-bats.

Though he tried to make the team in spring training the following year, Monty just didn’t have it any more. In April he turned 36 and the Sox were going to go with Fisk and Gary Allenson.

In 1980 and 1981, Monty worked in sports radio and did some Red Sox games on radio as the color commentator. In 1982, WSBK, Channel 38, was looking to hire a new color commentator and interviewed Tony Conigliaro for the position. But when Tony’s heart attack removed him from consideration, Monty was hired to do the color on Red Sox telecasts. He worked as Ned Martin‘s partner doing TV for the Red Sox for 17 years, right up through the 1995 season, when Channel 38’s run with the Red Sox came to a close.