[3][4] Tobolski was born and raised in McCook, Illinois, where he currently lives with his wife and daughter.
He played basketball for head coach Gene Pingatore during his time at St. Joseph.
Additionally, he received endorsements from numerous other officials in the district including U.S. Representative Dan Lipinski State Senators Don Harmon, Tony Munoz and Martin Sandoval, State Representatives Elizabeth Hernandez, Karen Yarbrough and Michael Zalewski, President of the Metropolitan Water Reclamation District Terrence J. O'Brien and twelve local mayors.
[11] On March 6, 2020, Tobolski turned in his resignation from his Cook County Commissioner role, effective at the end of the month, amid a federal probe.
Local Democratic Committeepersons appointed Frank Aguilar, a former Republican member of the Illinois House of Representatives from Cicero to succeed Tobolski.