One of the points that can be made in regards to players that played for the most franchises is the fact that they either played in the 19th century or after 1980. In between, there was a loyalty that players had to a particular organization and even if a player was traded a couple times, odds are no player would play for 8 or more teams. Out of the 235 players in the history of MLB who have played for 8 or more teams, less than 20 of them played between the years of 1925-1970. And among those was a LHP by the name of Dick Littlefield, who started his tour around different baseball cities in 1950.
Dick Littlefield will forever be the answer to the following trivia question- "Who was traded to the Brooklyn Dodgers in the deal that was supposed to send Jackie Robinson to the New York Giants after the 1956 season?" Of course, Robinson would refuse to play for the Giants, instead opting to retire- rather than play for the rival Giants. Another account had Robinson already deciding privately that he planned to retire- even if he were still property of the Dodgers. Our friends at SABR determined that it was more the latter- as a note from Robinson to the Giants owner was found with Robinson apologizing to the Giants saying he would have been happy to play for the organization had he not made the decision to retire after the 1956 season. Littlefield was returned to the Giants, who would then trade him to the Chicago Cubs.
Littlefield was signed as an amateur free agent by the Boston Red Sox in 1946. He made his big league debut in 1950, pitching in 15 games for the Sox. It was December of 1950 that Littlefield was dealt for the first time, to the Chicago White Sox in a five player trade. After a year in Chicago, Littlefield was dealt in November of 1951 to the St Louis Browns in an 8 player trade. A couple months would pass and then Littlefield would get traded again- this time to the Detroit Tigers in a 7 player trade. In August of 1952, he was dealt from the Tigers back to the Browns- where he would finish out the rest of 1952, all of 1953 and the first part of 1954- when the Browns had relocated to Baltimore.
After almost two full seasons playing for one organization (though the team had moved), Littlefield was traded from the Orioles to the Pittsburgh Pirates for Cal Abrams. A little less than two years to the day, on May 15, 1956, Dick was traded along with another player to the Cardinals in a deal that sent Bill Virdon to the Pirates. Just a month later, he was involved in a 9 player trade going from the Cardinals to the New York Giants in a deal that involved Red Schoendienst and Alvin Dark. That set the stage for the deal after the season between the Giants and Dodgers.
After the Robinson deal was voided, Littlefield was traded from the Giants to the Chicago Cubs in a 4 player trade on April of 1957. In 1958, he was purchased by the Milwaukee Braves from the Cubs, where he became a teammate of Schoendienst. He only appeared in 4 games for the Braves and spent the rest of the season in AAA. He spent the entire 1959 season and part of the 1960 season pitching in the minors for the Braves organization. He spent the rest of 1960 pitching in the minors for the Philadelphia Phillies organization. He pitched in the minors for the Angels in their inaugural season of 1961 and finished his career in the minors for the Angels and Phillies organizations in 1962.
It was uncommon for players in the 1950s and 1960s to play for a bunch of different teams. Dick Littlefield pitched for 8 different clubs, one of which played in two different cities. He also pitched for two different MLB teams at the minor league level and temporarily was property of the Brooklyn Dodgers. He managed the Dallas Fort Worth Rangers for half of the 1962 season when he was finished as a baseball player. He worked in the tool and dye business before passing away on November 20, 1997 at age 71 in Detroit Michigan.