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The nickname ''Monsters of the Midway'' was originally applied to the University Of Chicago "Maroons", a strong college football team under the leadership of Amos Alonzo Stagg . "Midway" is a reference to the Midway Plaisance , a long, green swath of Boulevard space bordering the southern end of the campus between 59th and 60th streets and running from Jackson Park to Washington Park on Chicago 's South Side. The U of C decided to drop its football program in 1939, about the time when the Bears became dominant in the NFL; the tag was appropriated by the Bears, even though their home turf was Wrigley Field on the North Side of the city (roughly 12 miles from the Midway).

The NFL's Arizona Cardinals , who were originally the Racine Normals (named for the street on the South Side of Chicago where they played; the team eventually became the Chicago Cardinals), received their first uniforms as hand-me-downs from the University of Chicago. The faded maroon was thought by the club's president to be a "cardinal" red color, so the team adopted "Cardinals" as its nickname. Through the years, the Cardinals were typically overshadowed by the Bears. Had the Chicago Cardinals enjoyed the success of their crosstown rivals, perhaps they would have inherited the nickname "Monsters" from the Maroons and not just their jerseys.

"Monsters of the Midway" is also used as a nickname for three of the greats who have played , Dick Butkus and Mike Singletary .

TSR also published a game entitled "Monsters of the Midway" in a 1982 edition of their magazine ''The Dragon.'' It was a football simulation with various fantasy characters taking the place of football players.