Jonathan Shields is in his second season as the Chiefs’ Assistant Coach after helping lead last year's team to a 20-win season. As a Volunteer Assistant Coach in 2016-2017 he helped guide Waubonsee to a share of the Illinois Skyway Collegiate Conference (ISCC) title, a Region IV crown and an NJCAA Division II National Tournament berth. As a matter of fact, he is the only person in Chiefs’ history to both play and coach in a National Tournament for Waubonsee. Shields played two seasons for head coach Dave Heiss, and brings that familiarity with the Chiefs’ program and system to the sidelines.     

Shields is a 2006 graduate of Chicago’s Washington High School where he was on the varsity for three years, the last two as a starter. The 6’2” shooting guard helped lead the Minutemen to back-to-back Red East Conference titles, earning All-Area and All-Conference Honorable Mention. His senior year the Minutemen set a school record for wins and reached the Chicago Public League title game, falling just short of knocking off top-seed Simeon which was led by future N.B.A. Most Valuable Player Derrick Rose.

As a freshman at Waubonsee during the 2007-2008 season, Shields earned All-ISCC Second Team honors helping the Chiefs garner perhaps the program’s most unexpected Region IV Championship. The sixth-seeded Chiefs upset the top three seeds en route to winning the title and earning a berth in the NJCAA Division II National Tournament with a .500 record. Shields’ last second three-pointer propelled Waubonsee past second-seeded Oakton in the semi-finals. As a sophomore he again earned All-ISCC Second Team honors, finishing his Waubonsee career with a solid 10 points-per-game average.

Shields went on to Livingstone College in North Carolina before returning home due to family issues. He can often be found on a basketball court giving individual skills instruction to youth players or conducting training sessions. For the last five years he has been the head coach of A Lot of Game, a Pro-Am tournament team that plays around the Chicago area. Shields currently lives in Oswego and works for the Caterpillar Corporation.