Monday attended Booker T. Washington High School (Tulsa, Oklahoma), where he won four state titles and the 1977 Junior National championship. He never lost a dual from seventh grade through the end of high school and finished with a record of 140-0-1.
As an All-American at OSU, Monday won the NCAA title in 1984 at 150 pounds. His collegiate record of 121-12-2 contributed to the Cowboys winning two Big Eight titles. He won the 1989 World Championship and a series of USA Freestyle championships in 1985, 1988, 1991, and 1996. He won the Olympic Championship in 1988 in a 2-2 overtime against the Soviet Union's Adlan Varaev.