After graduating from Jersey Community High School, Rich Montgomery earned a bachelor of science degree in social studies and physical education from Culver-Stockton College and a master's degree from Northern Illinois University. He coached wrestling in Illinois for 27 years, beginning in 1979 for two years at Jerseyville. He moved to Sterling Newman Catholic High School until 1991 before completing his wrestling coaching career at Rock Falls High School, where he now serves as the school's Athletic/Activities Director. Rich's teams posted a 420-237-5 dual meet record, claiming 62 state qualifiers, 36 state medalists and 17 individual state champions. His 1985 Newman team captured the Class "A" State Championship, and the 1989 team finished third. Inducted into the IWCOA Hall of Fame in 2002, Rich was a Grand Marshall at the 2010 individual state tournament. The 1985 IWCOA Class A Coach of the Year, he was also honored as IWCOA Administrator of the Year in 2002 and 2010 and the IWCOA Man of the Year in 2012. He received the IWCOA Lifetime Achievement Award in 2014. Currently president of the IWCOA, Rich serves on the board of the Illinois chapter of the National Wrestling Hall of Fame and as the National Wrestling Coaches Association state representative.