30 greatest MLB players to never make the playoffs
26. Dom DiMaggio
While his Hall of Fame brother was busy winning World Series titles and marrying Marilyn Monroe, Dom DiMaggio toiled away for the Boston Red Sox, never making a trip to the Fall Classic. The younger DiMaggio brother was a seven-time All-Star and an excellent player in his own right.
Dom DiMaggio is frequently overlooked given who his brother is and the fact that he shared the Fenway Park outfield with Ted Williams for most of his career, but he may be the most underrated player of his generation. DiMaggio actually led all MLB players in hits during the 11 years that he played in the league. He still ranks in the top ten in multiple offensive categories for the Red Sox.
Dom showed he was more than just a famous last name, averaging over 100 runs per 162 games for his 10-year peak. His career was interrupted by World War II, where he served in the Navy in spite of his poor eyesight without his trademark round glasses. DiMaggio had his finest season in 1950, hitting .328/.414/.452 with 131 runs and 11 triples. He retired after playing only three games in 1953 and picked up 1,680 hits in an 11-year career.
After his playing days ended, DiMaggio became a very successful businessman, dabbling in materials and chemical engineering, real estate, restaurants and other commercial ventures. He nearly purchased the Red Sox after the death of Tom Yawkey, was a co-founder of the Boston (now New England) Patriot and was instrumental in the creation of the Major League Baseball Players Association.