The painting became one of Rockwell's most iconic baseball-themed works and came to symbolize the Cubs' "lovable loser" image, throughout.

[2] Before a doubleheader at Braves Field between the Boston Braves and the Chicago Cubs on May 23, 1948, Rockwell approached both teams with the intention of creating a portrait of a visiting team's dejection in contrast elation of hometown fans.

[3] A number of Cubs players and manager Charlie Grimm agreed to pose in the dugout to be photographed.

As spectators filled the stands, Rockwell handpicked a number of them and instructed them to mimic expressions of delight or scorn.

Additionally, a batboy for the Braves, Frank McNulty,[2] had to be convinced to pose in a Cubs jersey in front of the dugout.