- Coach Stewart has been involved in the coaching of several teams and sports at both the high school and community rep levels of athletics since 1984. Jim has served as both head basketball and head baseball coach at three YCDSB schools, with the most recent being St. Theresa of Lisieux CHS (2002-2015). He won a YRAA basketball championship in his first year of coaching, along with numerous YRAA Central Division titles in baseball and basketball.
- His high school baseball and basketball teams have enjoyed successful excursions to the USA, including a 2010 trip when the STL Basketball Lions captured the gold medal in the Pioneer USA Invitational Tourney in Springville, New York. Upon retirement after 33 years of successful teaching and coaching, Jim was honoured by the York Region Athletic Association in June 2015 for “an outstanding career in service to the students of York Region in the Field of Athletics.”
- As a Pitching Coach, Third Base Coach, and Head Coach, Jim coached in the YSBA for 10 seasons and won four championships—three with the Newmarket Hawks (2004-2006) and one with the Aurora Jays (2007). Jim retired from rep coaching after the 2007 season.
- In July 2015, Jim was lured out of retirement and was named head coach of Team Ontario 16U. The 16U’s made it to the CPBL semifinals in 2016, losing 3-1 to the Ontario Blue Jays in a hard-fought game. The team earned a winning record in its USA tourneys in Pennsylvania, Florida, Michigan, Ohio, and Indiana. In October 2016, his team—with 15 new players and in full rebuild mode — went 3-1 in a World Series event in Chicago, Illinois. Included in those victories were two walk-off wins.
- In Fall 2016, Jim was named Team Ontario’s Director of Recruiting as well as Education Compliance Officer to go along with his ongoing coaching duties. It is Coach Stewart’s mandate to scout and refine student-athletes who will build the Team Ontario Astros brand and to prepare all the organization’s players for academic success in their post-secondary destinations. This involves collecting players’ report cards, counselling all players regarding academics, coordinating S.A.T. sittings and preparatory activities, and advising at-risk students.
- In Fall 2017, Jim was named Director of Communications for the Team Ontario Astros as his organizational portfolio expanded to field procurement as well.
- After a successful 2018 season as bench coach on Coach Booth’s 18U staff, including a terrific 10-3 road trip through the American Midwest in July, Jim has joined Coach Presutti’s 15U coaching staff in 2019 to perform the same role as bench coach and bullpen coach to help develop this promising team.