Arguably the greatest pure hitter of all time, Theodore Samuel “Ted” Williams played 21 seasons in left field for Boston, and is widely regarded as the greatest Red Sox baseball player ever to put on a uniform.

Williams, who was later nicknamed “Teddy Ballgame” or “The Splendid Splinter,” grew up in San Diego, California, and debuted for the Red Sox in 1939 at the age of 20. There is only one trading card from Williams’ rookie season. That Play Ball card, which shows Williams centered in the frame with his eyes focused on the camera while finishing his prototypical swing, is extremely collectible.

A 16-time All Star and two-time American League Most Valuable Player (MVP), Williams quickly established himself as one of baseball’s most feared hitters. In just his third season, Williams had one of the best years in baseball history, hitting .406 with a league-leading 37 homeruns. In fact, Williams’ 1941 season marks the last time a Major League Baseball player batted over .400, which is one reason why his 1941 Play Ball card is one of the most sought-after pieces of baseball memorabilia.

Unfortunately for Williams, his career statistics were not as impressive as they might have been because he missed all or part of five seasons serving as a pilot in the Marine Corps during both World War II and the Korean War. Had he played those five seasons, Williams may have challenged Babe Ruth’s record of 714 homeruns. Instead, he had to settle for 521, but Williams retired with the highest on-base percentage of all time (.483) and the highest batting average (.344) of a player to hit 500 or more homers.

After Williams’ service in World War II, Leaf Gum was the first candy company to release a Williams baseball card—it was part of Leaf’s 1948-1949 set. The brightly colored card shows a stoic Williams in a gray-and-blue flannel uniform set against a red background. It is tough to find this card in high-grade because this particular Leaf set was full of poorly centered cards and had bad print quality. As it turned out, this was the last Williams card Leaf would make—by 1950 the company had been bullied out of the market by Topps and Bowman.

Williams was not included in Bowman’s first two sets of baseball cards in 1948 and 1949, but he was pictured in the 1950 Bowman set when the company upgraded its cards to full color. As was the case with many Williams cards, the Bowman depicted Williams finishing his near-perfect swing, his Hillerich & Bradsby Louisville Slugger bat strewn over his right shoulder.

Williams continued to star for Boston until his retirement in 1960—he went out in style, becoming one of the only players to hit a homerun in his last Major League at-bat. The hi...

Throughout his career Williams was continually compared to New York Yankees’ outfielder Joe DiMaggio as the two starred for rival teams. While they were playing, fans joked that they should be traded for each other because Williams, who hit left-handed, would thrive with the short right field fence at Yankee Stadium, and DiMaggio, who hit right-handed, would excel with Fenway Park’s short porch in left field. In fact, a trade almost happened.

Because of this rivalry, autographed pictures of Williams and DiMaggio together, as well as other memorabilia such as autographed bats of the two players, are very popular items. Short of that iconic object, some collectors have sought autographed copies of the July 8, 1950 edition of “TV Guide,” which featured the pair on the cover.

While Williams’ individual statistics may trump those of DiMaggio, the one thing missing from Williams’ career was a World Series championship, a feat DiMaggio accomplished nine times. Unfortunately Williams passed away in 2002, just two years before his Red Sox won their first World Series title in 86 years.

Williams’ collectibles continue to be some of the most popular baseball artifacts around, and the most popular among retired Red Sox. In addition to trading cards, other prized items are Williams statues, autographed baseballs and bats, and game-used bats, which are noticeably lighter in weight than many other bats—Williams felt that a light bat was key to his quick, compact swing.

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