Dick Littlefield – Baseball Player Biography, Career, Net Worth Information

Dick Littlefield stands out in baseball history as one of the most well-traveled players of his time. The left-handed pitcher bounced around nine different Major League Baseball teams between 1950 and 1958, constantly moving in an era when trades weren’t nearly as common as today.

His baseball journey took him from the Boston Red Sox all the way to the Milwaukee Braves, with a whole patchwork of stops in between.

Richard Bernard Littlefield wrapped up his professional baseball career in 1958 after finishing his last season with the Milwaukee Braves. That capped off nine years in the majors. Born and raised in Detroit, Michigan, Littlefield served in the U.S. Navy during World War II before he chased his baseball dreams.

You can see the story of a determined pitcher in his career stats. He faced plenty of challenges but stuck with the game he loved.

Maybe the wildest part of his career? He got thrown into one of baseball’s most famous trades that never actually happened. In December 1956, someone traded him and $30,000 cash to the Brooklyn Dodgers for Jackie Robinson. But Robinson decided to retire instead of reporting to the New York Giants, so the whole deal fell through. That failed trade is still one of the most fascinating little footnotes in baseball.

But there’s more to Littlefield’s story than stats and transactions. You get a real glimpse into the human side of pro baseball in the 1950s.

Early Life and Background

Richard Bernard Littlefield was born in Detroit, Michigan, on March 18, 1926. He grew up in a working-class neighborhood during the tough years of the Great Depression.

His path to pro baseball included a stint in the military during World War II and some early athletic success in both baseball and hockey.

Family and Childhood in Detroit

Dick Littlefield spent his childhood in Detroit, Michigan, during the 1930s. His full name was Richard Bernard Littlefield, but everyone just called him “Dick” throughout his baseball career.

Detroit in those days was a major industrial city, but times were hard. Like a lot of families back then, the Littlefields probably faced some real economic pressure.

Detroit has always been a baseball town, and the Detroit Tigers were a big deal. That might’ve nudged Dick toward the sport. The city’s baseball scene gave kids like him plenty of chances to play organized and amateur baseball.

His Detroit roots stayed important to him. Later, he’d get the chance to play for his hometown Tigers in the majors, which must’ve felt pretty special.

Education and Amateur Baseball Experience

Littlefield went to Cooley High School in Detroit, but he left after 11th grade. That was actually pretty common in the 1940s, especially for guys chasing athletic careers or dealing with family money issues.

By 1941, when he was just 15, Littlefield was already making a name for himself in Detroit’s amateur baseball leagues. He had enough skill to compete with older players.

He wasn’t just a baseball guy, either. Littlefield played amateur hockey, too, showing off the kind of versatility you saw in a lot of Detroit athletes. The city’s strong hockey culture gave him another outlet for his competitive streak.

Those early days in Detroit’s local leagues sharpened his skills. Facing tough competition as a teenager probably helped him get ready for the pros.

Military Service in the United States Navy

World War II interrupted Littlefield’s baseball dreams. He enlisted in the United States Navy in March 1944, just after turning 18.

He served for over two years, from March 1944 until May 1946. That covered the final years of the war and a bit beyond.

Serving in the Navy set back his pro baseball career by more than two years. A lot of players from his generation went through the same thing.

When he finished his Navy service in May 1946, Littlefield was eager to get back to baseball. The Red Sox signed him about a month after his discharge, seeing something in him despite the time away from the game.

Professional Baseball Career Overview

Dick Littlefield suited up for nine different Major League Baseball teams during his eight-year career from 1950 to 1958. People mostly remember him for all those team changes and for being part of that strange Jackie Robinson trade.

Major League Debut and Early Years

Littlefield made his Major League debut on July 7, 1950, with the Boston Red Sox. The Detroit-born lefty quickly earned a reputation as a journeyman.

His early career was a bit of a whirlwind. He started with Boston in 1950, then got traded to the Chicago White Sox in 1951. In 1952, he moved again, this time to his hometown Detroit Tigers.

Littlefield showed some promise but had one big weakness: control. He walked too many batters, and that issue followed him everywhere.

Despite the control problems, teams kept giving him chances. His ability to pitch from the left side made him valuable to clubs needing more arms.

Key Trades and Transactions

Littlefield’s career was a carousel of trades. After Detroit, he joined the St. Louis Browns in 1952 and 1953. Then, when the Browns moved, he went with them to become the Baltimore Orioles in 1954.

The Pittsburgh Pirates gave him his longest run, from 1954 to 1956. In 1954, he went 10-11 and actually led the team in wins. That was his best season, even if he never quite got over .500.

After the 1956 season, he got caught up in that wild trade with the New York Giants and Brooklyn Dodgers for Jackie Robinson. But when Robinson retired, the whole thing went up in smoke. Littlefield then ended up with the Chicago Cubs the next spring.

He also spent time with the St. Louis Cardinals in 1956 and wrapped up his career with the Milwaukee Braves in 1958.

Pitching Style and Skills

Littlefield pitched left-handed, stood 6 feet tall, and weighed about 180 pounds. He both batted and threw left, which always made him a handy option for teams looking for a southpaw.

Control was his big issue. Too many walks limited his effectiveness and led to all those team changes. He just never quite settled in as a regular starter.

Still, he managed a career record of 33 wins and 54 losses with a 4.71 ERA over 245 games. He never finished a season with more wins than losses.

He shared clubhouses with some real legends—Ted Williams, Roberto Clemente, Stan Musial, Willie Mays, Ernie Banks, Hank Aaron, and Warren Spahn.

Major League Teams and Notable Moments

Dick Littlefield pitched for nine teams during his eight-year career from 1950 to 1958. His journey included the Boston Red Sox, Chicago White Sox, Detroit Tigers, St. Louis Browns, Baltimore Orioles, Pittsburgh Pirates, St. Louis Cardinals, New York Giants, Chicago Cubs, and Milwaukee Braves.

Boston Red Sox Years

Littlefield made his big league debut with the Boston Red Sox on July 7, 1950, at age 24. Born in Detroit, he’d already served in the U.S. Navy before starting his pro baseball career.

While with Boston, he played alongside Hall of Famer Ted Williams. Not a bad way to kick off a career.

His time with the Red Sox didn’t last long. Those control issues kept popping up.

Boston traded him to the Chicago White Sox in 1951, and that started a long run of team changes.

St. Louis Browns and Baltimore Orioles Transition

After his stints with the White Sox and Tigers, Littlefield joined the St. Louis Browns in 1952 and 1953. He even got to play with the legendary Satchel Paige during that time.

The Browns relocated to Baltimore after the 1953 season and became the Baltimore Orioles. Littlefield stuck with the team during this historic transition.

He was one of the few guys who experienced that move from St. Louis to Baltimore firsthand. That relocation was a big deal in baseball history.

Littlefield handled the change and kept pitching, even as the franchise struggled.

Detroit Tigers and Pittsburgh Pirates Contributions

Littlefield went back to his hometown, joining the Detroit Tigers in 1952. Playing for the team he grew up watching must have been something.

His longest run with any club was with the Pittsburgh Pirates from 1954 to 1956. In 1954, he put up a 10-11 record.

Those 10 wins actually led the Pirates that year, which says a lot about both his contribution and the team’s struggles. That was probably as close as he came to a winning season.

He shared the field with Roberto Clemente during his Pittsburgh years. That stretch was about as stable as things got for Littlefield.

New York Giants, Chicago Cubs, and Milwaukee Braves Tenure

Littlefield landed with the New York Giants in 1956. He played with Hall of Famer Willie Mays there.

After the 1956 season, the Giants traded him to the Brooklyn Dodgers for Jackie Robinson. But Robinson retired, and the deal vanished.

The Chicago Cubs picked up Littlefield in 1957. He played alongside Ernie Banks, another future Hall of Famer.

He finished up with the Milwaukee Braves in 1958. There, he was teammates with Hank Aaron and Warren Spahn.

Littlefield’s last big league game came on May 30, 1958. By then, he’d pitched for nine teams, ending with 33 wins, 54 losses, and a 4.71 ERA in 245 games.

The 1958 Retirement Season

Dick Littlefield’s final season in Major League Baseball was with the Milwaukee Braves in 1958. That wrapped up a nine-year career and capped off his journey through nine different teams.

His time with the Braves was short—just four games and a handful of innings. It was a pretty quiet ending to a long baseball road.

Performance and Statistics in 1958

Littlefield got into only four games for the Milwaukee Braves that season. He pitched a total of 6.1 innings, all in relief appearances.

His numbers that year were modest. He didn’t pick up any wins, took one loss, and posted a 4.26 ERA. He allowed seven hits and three earned runs.

He struck out seven and walked just one, which was actually a pretty good strikeout-to-walk ratio for him.

His last game was on May 30, 1958, against the Pittsburgh Pirates. In that outing, he pitched just a third of an inning, gave up one hit, and struck out one.

Compared to earlier years, his playing time really dropped off in 1958. Just the year before, he’d thrown 65.2 innings for the Chicago Cubs.

Final Major League Appearances

Dick Littlefield made his last Major League appearance on May 30, 1958. He came into the game against Pittsburgh as a reliever and faced just a handful of batters before the manager pulled him.

That game against the Pirates was his fourth and final outing of the season. By then, at 32, he wasn’t the same pitcher who’d once started 22 games in a year.

Milwaukee used him only out of the bullpen. He never started a single game during his short time with the Braves.

The Braves were flying high after winning the World Series in 1957. Littlefield’s limited role just showed how deep the team was, and, honestly, how much his skills had faded.

After that last game, he never played in the majors again. His career wrapped up after eight years and 243 games.

Reasons for Retirement

Littlefield’s retirement seemed to come down to his declining performance and fewer chances on the mound. His ERA had crept over 5.00 in his last seasons with the Cubs.

At 32, he was hitting the usual retirement age for pitchers back then. His career record of 33 wins and 54 losses told the story of a tough road in the big leagues.

Pro baseball just doesn’t have much room for struggling veterans. The fact that he bounced around so much probably meant teams didn’t see him as a long-term piece.

His last season with Milwaukee looked like a final shot to show he still had it. The Braves barely used him, which pretty much said it all.

He and the game might’ve both realized it was time to move on. His pitching just wasn’t there anymore, not for the big leagues.

The Jackie Robinson Trade Incident

On December 13, 1956, Dick Littlefield landed in the middle of one of baseball’s weirdest trades. The Brooklyn Dodgers tried to send Jackie Robinson to the New York Giants for Littlefield and $30,000, but Robinson immediately retired and killed the deal.

Details of the Voided Trade

The Dodgers made the trade official on December 13, 1956. They sent Jackie Robinson to their arch-rivals, the New York Giants, and got pitcher Dick Littlefield plus $30,000 in return.

Robinson was 37 and had just finished a season hitting .275 over 117 games. He played all over the field—second base, third, first, even the outfield.

Trade Details:

• Date: December 13, 1956
• Teams: Brooklyn Dodgers to New York Giants
• Players: Jackie Robinson for Dick Littlefield
• Cash: $30,000 included with Littlefield

Within hours of the trade, Robinson told the Giants he wouldn’t report. He’d already taken an executive job at Chock Full o’ Nuts before the trade even happened.

On January 14, 1957, Robinson sent a letter to Giants owner Horace Stoneham. He wrote, “After due consideration, I have decided to request to be placed on the voluntary retired list as I am going to devote my full time to business opportunities that have been presented.”

Because Robinson didn’t show up for the Giants, the trade got voided.

Reactions and Impact on Baseball History

Brooklyn fans never had to watch Robinson wear a rival’s uniform. The trade would’ve made the civil rights icon play for the Dodgers’ most hated enemy.

Robinson told the Giants his retirement wasn’t about the trade. Still, the timing made it seem like he just couldn’t see himself leaving Brooklyn.

Dick Littlefield never put on a Dodgers jersey because the deal fell apart. He kept bouncing around the league, building his reputation as one of the most traded players in baseball.

That whole incident closed the book on Robinson’s 10-year run with Brooklyn. He’d grabbed the 1947 Rookie of the Year and the 1949 National League MVP while with the Dodgers.

Robinson’s Career Highlights:

• .311 lifetime batting average
• Six-time All-Star
• 1955 World Series champion
• First African-American player in modern MLB

National League president Warren Giles signed off on Robinson’s retirement on January 16, 1957. That ended one of baseball’s biggest careers and shut the door on a trade that never happened.

Legacy, Personal Life, and Net Worth

Dick Littlefield’s baseball story is mostly about his constant moves and his quieter life back in Detroit after baseball. His modest earnings were typical for players in the 1950s—not exactly the big money you see now.

Reputation as a Journeyman Pitcher

People called Dick Littlefield “Baseball’s Leading Gypsy” during his nine-year career from 1950 to 1958. He suited up for nine different teams, which made him one of the most traveled players in the game’s history.

He tied Bobo Newsom’s record for playing with the most teams, but did it in just nine years while Newsom took 18.

All those trades were a weird mix of frustration and comedy. Littlefield joked, “Every time I’m traded, they call me in and say how sorry they are to see me go,” and, “They really wanted to keep me, but the other club demanded me, or the whole deal was off.”

His family definitely took a hit from the constant moving. His wife sometimes heard about trades on the radio before he did. His kids had to keep changing schools, and one daughter spent just a single day at a Pittsburgh school before another trade sent them packing.

Post-Retirement Life and Passing

When he retired in 1958, Littlefield moved back to Detroit. He’d been born there on March 18, 1926, and went to Cooley High before serving in the Navy from 1944 to 1946.

He lived a pretty quiet life after baseball. He married Naoma Clark in October 1946 after meeting her on a blind date, and they had three kids.

Richard Bernard Littlefield died on November 20, 1997, at age 71 in Detroit. His journey had taken him all over the country, but in the end, he came home to Michigan.

Estimated Career Earnings and Net Worth

Littlefield pitched in an era when baseball salaries just weren’t what they are today. Honestly, with a career record of 33-54 and bouncing around between teams, he probably didn’t make a fortune.

Most players in the 1950s took home somewhere between $5,000 and $15,000 a season. As a journeyman pitcher, Littlefield likely earned closer to the bottom of that range for most of his time in the majors.

Nobody ever published his financial details, but his quieter life in Detroit after baseball hinted at pretty modest means. The frequent trades and constant team changes didn’t exactly help him negotiate better pay or build up much wealth from the game.