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2. 1997-99 Alternate
On the cusp of the new millennium, the Cubs were at the epicenter during one of the most polarizing periods of MLB's storied history. Sammy Sosa, Mark McGwire: long ball battle. Love it or hate it, the summer of 1998 home run in-season derby provided more than enough excitement for fans.
Sept. 23, 1998, Sammy Sosa cranks home runs 64 and 65 at Milwaukee County Stadium. The N.L. MVP was wearing the blue alternate Cubs jersey when he smashed those long balls. When I think of Sammy Sosa, I think of the alternate uniform and him trotting around the bases following a moon shot. This brings back a lot of memories as I was just beginning to not only understand but appreciate the sport of baseball. Nearly two decades later, the Cubs were able to break one of professional sports' most storied curses in a uniform similar to this after winning the 2016 World Series.