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Bill O’Leary, Milton/Janesville Craig

04/01/2023, 12:15pm CDT

Bill was born in Janesville, Wisconsin on Decemer 15, 1952. His parents were Mary (Fanning) and Jim O'Leary. He grew up on a farm in Milton, with his 4 siblings. His work ethic was established during this time but he knew he wasn't cut out to be a farmer. He attended a one room school for the first six years of his education. While attending Milton High School he participated in football, wrestling and track. He was named All-Conference in football and was the MVP of the team his senior year. 

After graduation, he attended UW-Whitewater where he played football for two years under Forrest Perkins. In 1974 he graduated with a B.S. in Special Education , and was hired by the Janesville Public Schools. He taught there for 35 years, at Edison Junior High for 17 years and then Craig High School for 18 years.

His coaching career started the day he started teaching. He coached football for 35 years, basketball for 4 years and wrestling for 25 years. He was an assistant coach in football under Ron Ganong, and Dan Thorpe before becoming the head coach in 2000. His teams qualified for the WIAA playoffs seven of the nine seasons he served as head coach. During his wrestling coaching career, Craig won 6 conference championships and sent many wrestlers to the WIAA State Tournament. 

After his retirement from coaching and teaching in 2009, he continued to coach youth sports in Milton. When the head coaching job opened in Milton High School in 2013, he took the job and lead the Red Hawks to 3 playoff berths and two conference championships. He was named Coach of the Year for the Badger North Conference in 2014.

When he stopped coaching in 2015, he found his way back to the field via radio. He has been broadcasting the Janesville High School football games on Big Radio since 2016. Bill is the color guy along side his partner Josh Golberg, the play by play guy and sports director. This year Bill and Josh added an additional broadcasting job covering the UW-Whitewater football games. He loves this gig.

Bill married his wife, Mary Ellen  in 1991. They have been happily married for 31 years. They have three children Mary Kate, Elizabeth and Patrick. He could not have accomplished all of this without the love and support of his family.  Bill also would like to send special thanks to his brother, Russ, who has coached beside him during his career. none of this sucess would have happened without him!

Tag(s): Hall of Fame