Bob Kennedy’s name might not ring out as loudly as some of his baseball peers, but his 18-year professional career is honestly a fascinating story of grit, adaptability, and service—both on and off the diamond. Born in Chicago in 1920, Kennedy broke into the majors as a teenager and ended up playing for six different teams before finally retiring in 1957.
Kennedy’s final at-bat happened on September 29, 1957, as a Brooklyn Dodger, in their last game before the team moved to Los Angeles. He became the final player to bat for the Brooklyn franchise. That quirky bit of history is just one of many interesting moments in a career that spanned nearly two decades and included military service in both World War II and the Korean War.
From his early days as a promising third baseman with the Chicago White Sox to his later years as a utility player, and then his shift into management and front office work, Kennedy’s journey through baseball really reflects how the game changed in mid-20th century America. His story weaves together championship moments, wartime sacrifice, and a lifelong love for baseball that went way beyond just playing.
Early Life and Path to the Major Leagues
Robert Daniel Kennedy grew up on Chicago’s South Side and started his journey to the big leagues during one of baseball’s messiest chapters. Born in 1920 to a family that loved the game, Kennedy honed his skills in youth leagues before the Chicago White Sox spotted him when he was just 16.
Family Background in Chicago
Robert Daniel Kennedy was born on August 18, 1920, right in the heart of Chicago’s South Side. His birth came during a rough time for baseball in the city, with the Black Sox Scandal still shaking things up at Comiskey Park.
Growing up in Chicago, Kennedy couldn’t escape the shadow of that scandal. Banned players like Buck Weaver kept showing up in amateur games around town. Kennedy’s coaches sometimes kept him out of games when Weaver played.
They worried that playing alongside a banned player could get Kennedy banned too. His coaches saw real major league potential in him and didn’t want to risk his shot.
That early brush with baseball’s strict rules stuck with Kennedy. The whole scandal left a mark on Chicago baseball and, honestly, on Kennedy’s entire career path.
Youth Baseball and High School Years
Kennedy went to Morgan Park High School in Chicago, where his athletic ability really stood out. He pitched in American Legion baseball and threw several no-hitters as an amateur.
Scouts across Chicago took notice of his strong arm. Kennedy’s pitching was solid, but his ability to play in the field made him even more appealing.
At the time, the Chicago White Sox were desperate for local talent. After years of second-division finishes, they needed to rebuild their fan base.
Kennedy’s mix of pitching and fielding skills got him noticed. At 6-foot-2 and 190 pounds, he was exactly the kind of player scouts wanted.
Signing with the Chicago White Sox Organization
In 1937, the Chicago White Sox picked up Kennedy as a third baseman when he was just 16. The team wanted to connect with local fans by bringing up homegrown players.
Kennedy’s first pro gig was with the Vicksburg Hill Billies in the Class C Cotton States League. He struggled, batting just .192 in 41 games and not hitting any home runs.
Still, the White Sox promoted him to the Dallas Steers in the Class 1A Texas League before that season wrapped up. That move showed they believed in his potential.
Once in Texas, Kennedy turned things around. He bumped his average up to .300, though he still didn’t show much power with just one extra-base hit in 60 at-bats.
The White Sox kept working with Kennedy in the minors. In 1938, he played for the Longview Cannibals, hit .261, and tied for the league lead with 14 triples.
MLB Debut and Early Career
Bob Kennedy broke into the majors as a teenager with the Chicago White Sox in 1939. He quickly started to make a name for himself as a promising third baseman.
Major League Debut in 1939
Kennedy made his big league debut on September 14, 1939, with the Chicago White Sox at just 19. The night before he signed, he was actually working as a popcorn vendor at Comiskey Park.
The young player from Chicago got his first shot in the majors in the last few weeks of the 1939 season. He debuted against the Philadelphia Athletics and had one at-bat, but didn’t get a hit.
His path to the big leagues was unusual back then. Kennedy skipped the minor leagues entirely, going straight from high school to the majors. That jump showed just how much faith the White Sox had in him.
First Years as Third Baseman
Kennedy took over as the White Sox starting third baseman in 1940, his first full season. He made some history by becoming the first teenager since 1900 to play 150 games in a season.
His defensive skills at third base impressed people right away. Kennedy had a strong, accurate arm and could make the long throw from third to first look easy.
He kept improving in those early years. Kennedy played regularly from 1940 through 1942, until military service put his career on pause during World War II.
Development as a Line-Drive Hitter
Kennedy turned into a reliable line-drive hitter during his early days with Chicago. He focused on making solid contact instead of swinging for the fences.
He valued consistency more than flashy stats. Kennedy worked hard to spray line drives all over the field, which kept his batting average steady.
His offensive skills matched his defense. While he never became a star hitter, Kennedy showed he could contribute at the plate and play solid defense at third.
Military Service and World War II Impact
Bob Kennedy’s baseball career took a big turn when he served as a Marine Corps pilot and flight instructor from 1943 to 1945 during World War II. When he came back to baseball in 1946, he managed to pick up right where he left off, and soon reached the best years of his career—including a World Series win with the Cleveland Indians.
Service in the United States Marine Corps
Kennedy enlisted in the Marine Corps in 1942 as World War II ramped up. He served as a pilot and flight instructor at the Marine Corps Air Station in Pensacola, Florida.
While at Pensacola, Kennedy trained other future big-leaguers. He even worked as a flight instructor for Ted Williams, who later became a baseball legend.
Kennedy and Williams played together on the base team during their service. That experience kept Kennedy’s baseball skills sharp while he served.
The Marine Corps noticed Kennedy’s strong arm and athleticism. He served for three years, from 1943 through 1945, right through the heart of the war.
Years Missed and Baseball Landscape During Wartime
Kennedy missed three full seasons of pro baseball because of the war. He was only 22 when he enlisted, losing out on what could’ve been some of his best years.
From 1943 to 1945, Major League Baseball kept going, but with a much thinner talent pool. Lots of stars were off serving, so teams leaned on older players or those who couldn’t be drafted.
The White Sox struggled without their key players while Kennedy was away. The team finished in the second division every year he was gone.
Baseball attendance dropped during the war. Many fans were overseas or focused on things at home.
Quality of play definitely took a hit, as teams used aging vets and players with exemptions. Kennedy returned to a very different game in 1946.
Return to the Major Leagues After Service
Kennedy came back to the White Sox in 1946 after his military service. His arm, made even stronger by flying planes, helped him switch to playing outfield.
He boosted his batting average to .258 in 1946, showing he still had it. The next year, he hit .262 and kept up the steady play.
His time in the military taught him discipline and leadership. Kennedy came back at 26, a much more mature player than when he left at 23.
The 1946 season was a real turning point. He settled into the outfield, leaving behind his earlier struggles at third base.
Military service ended up preparing Kennedy for his best years in baseball. In 1948, the White Sox traded him to Cleveland, where he’d have his biggest successes.
Peak Years and Career Highlights
Kennedy hit his stride when he moved from third base to the outfield, finally putting his strong throwing arm to good use. His years with the Cleveland Indians from 1948 to 1954 were the highlight of his career, including a World Series title.
Transition to Outfield and Team Roles
Kennedy’s career took a turn when he switched to the outfield in 1946. His strong arm, which had caused trouble at third, became a real asset in right field.
The White Sox realized his defense fit better in the outfield. Kennedy’s batting average rose to .258 in 1946 and .262 in 1947 as he got comfortable in his new spot.
On June 2, 1948, Kennedy got traded to the Cleveland Indians. The deal sent him to Cleveland for outfielder Pat Seerey and pitcher Al Gettel.
That trade worked out well for Kennedy. He found a home with the Indians and became a steady part of their lineup.
Cleveland Indians and World Series Champion
Kennedy’s best years were with the Cleveland Indians from 1948 to 1954. He hit .301 after joining the team mid-season in 1948, helping them win the World Series.
The 1948 World Series championship was the high point of Kennedy’s playing days. He played in three games as a defensive sub and picked up an RBI single in Game Two.
His most productive season was 1950. Kennedy set career highs with a .291 average, 79 runs, 157 hits, and 27 doubles.
From 1949 to 1951, Kennedy was the Indians’ regular right fielder. Those were his most consistent seasons as a starter.
Defensive Skills and Triple Plays
Kennedy’s defensive abilities made him valuable beyond his hitting stats. His strong right arm made Cleveland’s defense even better.
In 1950, Kennedy did something rare—he started two triple plays from right field. That kind of quick thinking and accuracy set him apart.
He could play almost anywhere. Kennedy filled in at first, second, and third base whenever teams needed him.
After leaving Cleveland in 1954, Kennedy hit the first grand slam in Baltimore Orioles franchise history. He launched it off Yankees pitcher Allie Reynolds on July 30, 1954.
His career totals: 63 home runs and 514 runs batted in over 16 seasons. Not huge numbers, but Kennedy’s defensive versatility made him a real asset.
Final Playing Years and Retirement in 1957
Bob Kennedy wrapped up his career with a handful of team changes that highlighted his veteran presence across several franchises. His last seasons included a historic grand slam for the Baltimore Orioles and the unique honor of being the last batter in Brooklyn Dodgers history.
Baltimore Orioles and Detroit Tigers Tenure
Kennedy joined the newly relocated Baltimore Orioles in 1954 after a trade from Cleveland. That move opened a new chapter for him, and he played a big part in helping the franchise settle into Baltimore.
On July 30, 1954, Kennedy made Orioles history by hitting the team’s first grand slam. He did it against Yankees pitcher Allie Reynolds, and that moment basically etched his name into Baltimore baseball lore.
His batting average during his Baltimore years stayed right in line with his career norms. Kennedy played both the 1954 and 1955 seasons with the Orioles and then moved on again.
In 1955, the Chicago White Sox bought Kennedy’s contract, bringing him back to his original team. But he didn’t stick around long before the White Sox sent him to the Detroit Tigers in 1956.
He only spent one season with Detroit. Kennedy brought some veteran leadership to the Tigers, though his playing time dropped off as his career wound down.
Brooklyn Dodgers and Final MLB Appearance
After Detroit released Kennedy in April 1957, he signed with the White Sox for a third stint. That lasted just a month before the Brooklyn Dodgers picked him up off waivers.
Kennedy played his final MLB game on September 29, 1957, at Connie Mack Stadium in Philadelphia. That game turned out to be the last one ever for the Brooklyn Dodgers.
At 3:36 PM, Kennedy stepped into the batter’s box with two outs and nobody on in the ninth. He faced Seth Morehead, a Phillies rookie, with the count at 2-2.
Kennedy flew out to center field, which made him the answer to a well-known baseball trivia question. He became the last batter ever for the Brooklyn Dodgers before they moved to Los Angeles.
The Phillies won that historic game 3-2, ending Brooklyn’s run in Major League Baseball. Kennedy’s last at-bat ended both his career and the Dodgers’ time in Brooklyn.
Notable Achievements in Last Seasons
In his final seasons, Kennedy still brought value as a veteran, even though his offensive numbers slipped. He finished with a career batting average of .254, a mark that showed his steady play through 16 seasons.
Back in 1950 with Cleveland, Kennedy put up career-best numbers—he hit .291, scored 79 runs, notched 157 hits, and smacked 27 doubles. That season was really the peak of his offensive game.
He pulled off a pretty rare defensive feat in 1950, starting two triple plays from right field. Only Charlie Jamieson had done that before, way back in 1928.
Kennedy won his World Series championship with the 1948 Cleveland Indians, the franchise’s last title. After Cleveland traded for him mid-season, he hit .301 and helped the team to victory.
He ended his career with 63 home runs and 514 RBIs in 1,483 games. Kennedy’s durability and consistency made him a solid contributor throughout his long run in Major League Baseball.
Coaching, Management, and Executive Contributions
Kennedy moved from playing into a baseball executive role, joining the innovative Chicago Cubs coaching system, managing the Oakland Athletics during their early Oakland years, and holding front office jobs with teams like the Houston Astros and San Francisco Giants.
Chicago Cubs College of Coaches
In 1962, Kennedy joined the Cubs’ unusual College of Coaches system as one of several rotating managers. Instead of a single manager, the Cubs tried out a series of “head coaches” who rotated leadership.
The system hadn’t worked well before Kennedy arrived. In 1961 and 1962, the Cubs finished in seventh place with rough records under coaches like El Tappe and Lou Klein.
Kennedy became the only manager in 1963, finally ending the experiment. He led the Cubs to an 82-80 record, a big jump from the previous season’s 59-103 finish.
The 1964 season didn’t go smoothly. The Cubs lost rookie Ken Hubbs in a plane crash, and they traded away promising Lou Brock to the Cardinals for veteran Ernie Broglio.
Kennedy managed part of 1965, then moved into the Cubs’ front office. His time in Chicago showed he could steady a struggling team and work with young talent like Ernie Banks and Ron Santo.
Managing the Oakland Athletics and Mustache Gang
Kennedy took over the Oakland Athletics in 1968, inheriting a team that had finished last in Kansas City the year before. Owner Charlie Finley brought him in to give the franchise’s first season in Oakland some much-needed stability.
The Athletics improved a lot under Kennedy. The team jumped from 62-99 in 1967 to 82-80 in 1968, finishing sixth in the American League.
He worked with young players who’d become the “Mustache Gang,” including future stars like Reggie Jackson and Sal Bando. The A’s championship years arrived after Kennedy left, but he definitely helped set the stage.
Even though the team improved, Finley fired Kennedy after just one season. The move surprised plenty of people, since Kennedy had turned things around for the franchise.
Kennedy’s short time with Oakland showed he could develop young talent and build a winning culture. His groundwork helped the A’s succeed in the early 1970s.
Front Office Roles with Multiple Teams
Kennedy spent more than two decades in various executive jobs after managing. He worked as a scout and farm system director for several teams, focusing on player development and baseball operations.
From 1969-1976, Kennedy worked with the Cardinals as director of minor-league operations and director of player personnel. He played a key role in building their farm system.
He returned to the Cubs as general manager from 1977-1981. The Cubs started strong in 1977, leading the NL East through July, but ended up finishing 81-81.
Between 1982 and 1985, Kennedy served as vice president of baseball operations for the Houston Astros under GM Al Rosen. The Astros grew into a competitive team during that time.
Kennedy’s last executive job came with the San Francisco Giants from 1986-1992, again working under Rosen. The Giants won their division in 1987 and took the National League pennant in 1989.
Throughout his front office career, Kennedy focused on player development and scouting. He helped build winning teams with smart personnel moves and strong minor league systems.
Legacy in Baseball and Family Connections
Bob Kennedy’s influence in baseball stretched way past his playing days, building a family legacy in the sport. His son Terry Kennedy became a four-time all-star catcher who even outperformed his dad in some ways, while Bob’s own contributions still get attention from baseball historians.
Influence on Future Generations
Kennedy’s baseball smarts and experience shaped several generations of players and execs. After he retired as a player in 1957, he spent 35 years in various baseball roles—coach, manager, scout, and front office executive.
He helped develop young talent with the Cubs, Astros, and Giants. Kennedy served as vice president of baseball operations for the Giants from 1986 to 1992, helping them win the 1987 division and the 1989 pennant.
Kennedy also influenced his own kids’ careers. His son Bob Kennedy Jr. pitched in the Cardinals minor league system for five seasons, then became a scout for the Cubs and Astros.
The elder Kennedy believed in teaching fundamentals and character. He even trained with Ted Williams during World War II at Pensacola, Florida, where both served as Marines.
Terry Kennedy’s Career
Terry Kennedy ended up as the most successful baseball player in the Kennedy family. He played 14 major league seasons from 1978 to 1991 and made four All-Star teams.
Terry’s stats topped his father’s. He finished with a .261/.314/.386 line, 113 home runs, and 638 RBIs, compared to Bob’s .254 average, 63 homers, and 514 RBIs.
Terry Kennedy’s Major Achievements:
- Four-time All-Star (1981, 1982, 1983, 1985)
- Two World Series appearances (1984 Padres, 1989 Giants)
- Named The Sporting News college player of the year in 1976
- First-round draft pick by St. Louis Cardinals in 1977
Terry later managed in the minors, keeping the family’s baseball leadership tradition alive. He was born in Euclid, Ohio, while Bob played for the Cleveland Indians, showing just how deep those baseball roots go.
Recognition and Hall of Fame Consideration
Bob Kennedy’s Hall of Fame case isn’t the strongest, but he does have some unique distinctions. Baseball historians have pointed out some pretty remarkable achievements that make him stand out from his era.
He was the first teenager to play 150 games in a season (1940). Kennedy was also one of just four players to serve in both World War II and the Korean War, alongside Ted Williams, Jerry Coleman, and Lloyd Merriman.
His last at-bat became a piece of baseball history. Kennedy’s 0-for-4 game on September 29, 1957, included the final at-bat by a Brooklyn Dodger before the team moved.
Even with a modest .254 career average, Kennedy’s 56 years in professional baseball show his lasting value to the sport. His work as an executive helped shape several franchises during key periods.
The Society for American Baseball Research has documented Kennedy’s unique spot in baseball history, but his stats just don’t quite reach typical Hall of Fame standards.
Net Worth and Personal Life
Bob Kennedy built up modest wealth during his baseball career, and modern estimates say his net worth reached several million dollars through playing contracts and executive roles. After his playing days, Kennedy moved into executive jobs and spent his final years in Arizona before passing away in 2005.
Career Earnings and Net Worth
Kennedy’s financial success came from both his playing days and his executive roles. During his 18 years as a player from 1939 to 1957, he earned salaries that were typical for the time—not exactly what you’d call huge by today’s standards.
The real money came after he retired. Kennedy landed several high-paying executive jobs that boosted his income. He served as general manager for the Chicago Cubs from 1976 to 1981.
He later took on senior executive roles with the Houston Astros (1982-1985) and San Francisco Giants (1986-1992). Those front office gigs brought steady income and benefits that far outpaced his player earnings.
Estimated Net Worth Sources:
- Playing career contracts (1939-1957)
- Managerial jobs with Cubs and Athletics
- Executive positions with MLB teams
- Scouting and player development work
Some sources peg Kennedy’s net worth between $10 million and $50 million. Those numbers might be inflated, though—celebrity net worth estimates can be all over the place.
Life After Baseball and Community Involvement
Kennedy stayed close to the game after he stopped playing. He worked as a scout and farm system director for the Cleveland Indians.
His family kept the baseball ties going strong. Kennedy’s son Terry became a four-time All-Star catcher and later managed in the minors, building a baseball legacy that went beyond Bob’s own career.
Kennedy split his time between baseball organizations and personal interests. People knew him for his strong work ethic and attention to detail—traits that served him well in the front office.
He kept up friendships with teammates and colleagues from his playing days. The 1948 World Series championship with the Cleveland Indians remained one of his proudest memories.
Kennedy’s knack for player development made him highly sought after. Teams wanted his eye for spotting and nurturing young talent.
Final Years and Passing
Kennedy spent his final years in Mesa, Arizona, which is honestly a pretty popular spot for retired baseball players. The desert climate, plus the closeness to spring training facilities, made it an appealing place for him.
He stayed involved in baseball circles even as he grew older. Kennedy kept up some consulting work and still called a lot of former colleagues and players friends.
On April 7, 2005, Kennedy died in Mesa at age 84. He lived a life that stretched across nearly the whole modern era of professional baseball.
Kennedy saw baseball change from the 1930s all the way into the early 2000s. His legacy isn’t just about stats—he also made a real impact on player development and team management.
Kennedy’s influence on the game reached far beyond his last at-bat for the Brooklyn Dodgers in 1957.
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