Raised on the near west side of Chicago, Jim’s parents sent him to the south side for high school and he graduated in 1965 from DeLaSalle High School (Chicago) as a football player. He went on to earn a BA in History from North Park College while he wrestled in intramurals.

 He returned to the west side of Chicago to teach and coach at Harrison High School from 1972-1980. As head wrestling coach, he compiled a record of 26-38. He had 24 Chicago Sectional (Regional equivalent) place winners, four City Tournament (Sectional equivalent) placers. He also served as Assistant Varsity & Frosh- Soph Football Coach 1972-1979 and Head Baseball Coach 1977-1980. He spent 1986 season at DeLaSalle as a Varsity Assistant Football Coach. From 1987-1991 he served at St. Joseph in Westchester as Varsity Assistant Football Coach and Head Sophomore Football Coach.

 He moved on to teach at Crane High School (Chicago) from 1980 to 2012 when he retired. While at Crane he began expanding his career as a Sport official in Wrestling, Baseball and Football. He has spent forty five years as an official with wrestling emerging as his primary sport. He has officiated 8 State Dual Team Tournaments and 1 Individual State Tournament on mat; 18 Individual State Tournaments as Scorer, Time Keeper and 5 as Weigh-In Official. Jim also served as the co-assignment chair for the Chicago Catholic League from 1997-2009. He was honored as the IHSA Official of the year for 2011-2012.

 Jim has officiated 17 Chicago Sectionals, 15 Chicago City Tournaments, 21 IHSA Individual Regionals, 12 IHSA Individual Sectionals, 12 IHSA Dual Team Regionals, and 10 IHSA Dual Team Sectionals. At the lower level he has worked 10 IKWF State Tournaments, 15 IKWF Regionals, 14 IKWF Sectionals, and 3 IKWF Dual State Tournaments. He officiated 3 USA National Folk Style Tournaments. He also officiated 6 IWF Kids/ Frosh-Soph State Tournaments including 2 as Head Official, Sectionals, Regionals and 5 IWF State Dual Meet Tournaments.

He has officiated 12 Coaches Alliance Frosh Soph State Tournaments, 20 Regionals, 18 Sectionals and has served at 11 Frosh Soph State Tournaments as Head Official. He also served as the Head Official for the Alliances two National Tournaments and the first two IWCOA Girls Open State Tournaments. In 2017, he served as a Grand Marshall for the IHSA Individual Wrestling State Tournament.

 In 2018, Jim was recognized at the IWCOA Frosh Soph/Girls State Championships for his 11 years as a head official and 12 years as a mat official. Since 2018 he has continued to serve as a table worker for the IWCOA Frosh Soph/ Girls State Championships. In 2019 Jim was recognized for his Lifetime Service to Wrestling by the IWCOA.

He has been the Plate umpire at the Cell and Wrigley Field for multiple Chicago Public Schools Championship Baseball games.

 He attributes his success to his wife of 51 years, Christine and his children Jennifer Hudson and James Paul Chaloupka, their spouses and his Champion grandchild Riley Hudson.