Maguire was the program director at 560 WQAM-AM from May 2015 to February 2018. He held numerous program director positions prior to his arrival in Miami. Maguire was at WQSN-AM in Kalamazoo, WLBY-AM in Ann Arbor, WTKA-AM in Ann Arbor, WSSP-AM in Milwaukee, KCSP-AM in Kansas City and KDKA-FM in Pittsburgh.
After his stint in South Florida, he became the director of programming at KIRO-FM in Seattle from March 2018 until August 2019. He moved on to SpokenLayer as a producer in April 2020. Maguire joined Barrett News Media as a columnist in September 2020.
Maguire then picked up two different positions. He started at WMVP-AM in Chicago as the Chicago White Sox Radio Network executive producer in December 2020. Maguire added duties as a writer with Barrett Sports Media during 2021.
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