For 86 years, Boston Red Sox fans were convinced their team was cursed. After selling Babe Ruth to the rival New York Yankees in 1919, it seemed as if Boston would never again win a World Series title. Then, in 2004, the drought ended with a shutout of the St. Louis Cardinals. For a while—the team captured another World Series in 2007—it even looked like the 21st century would belong to the Sox.

Despite all those years of misery, the Red Sox hardly lacked the great players that collectors covet. Ted Williams, Carl Yastrzemski, and Carlton Fisk all roamed the grass of Fenway Park. Today, with a budding generation of Red Sox fans known as “Red Sox Nation,” many collectors hope to gobble up relics of Red Sox past.

There is no doubt that the Red Sox are one of baseball’s most historically significant franchises. Even during their years of losing, Fenway Park remained a baseball Mecca, and fans in the Boston area and around the country collected Red Sox memorabilia as a means of enjoying a team that seemed perpetually destined to fail.

While many of today’s most popular Red Sox collectibles come from their championship seasons in 2004 and 2007—fans are still in drunken awe that they actually won—lots of collectors focus on vintage Red Sox goods.

In addition to cards, autographs, and jerseys of stars such as Williams, Yastrzemski, and pre-Yankees Ruth, collectors also desire team-oriented memorabilia. Some of the most popular antique Red Sox collectibles are programs and pennants.

Red Sox pennants vary in size (older ones are smaller), color (red, blue, and white are most common), and material (felt, plastic, and cloth were all used). One popular pennant is the 1968 white felt triangle that has a photograph of the entire team stitched on its face.

Collectors also seek game-day programs because these keepsakes allow them to get a feel for the day-to-day baseball environment. Red Sox programs are no different, and some of the most popular come from the 1960s, like a 1963 Red Sox-Yankees program that shows an overhead view of Fenway Park. In general, though, the most collectible Red Sox programs are the oldest...

Despite the collectibility of these items, as well as team photographs and ticket stubs, some collectors still insist on collecting by player. Although Williams and Yastrzemski get the most attention among Red Sox collectors, other Hall of Famers such as Cy Young, Wade Boggs, Jimmie Foxx, Lefty Grove, and Tris Speaker all spent significant time in Red Sox uniforms and are prized by many. Contemporary players such as David Ortiz, Kevin Youkilis, and Dustin Pedroia are also highly collectible.

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