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Jonathan Federman is a proficient legal writer and skilled litigator. As a former clerk in the Illinois Supreme Court, Jonathan knows what it takes to prevail at the trial and appellate levels. Jonathan understands that courts of law and public opinion value clarity and integrity in all facets of legal advocacy, and that is exactly what Jonathan provides on behalf of his clients.  

Jonathan’s practice includes representation of insurance company clients in disputes arising out of commercial general liability, professional liability, business auto, directors and officer and many other types of policies of insurance. Jonathan provides opinions to insurer clients faced with a potential claim as well as representing insurers engaged in declaratory judgment litigation. While Jonathan has proven that he is equipped to litigate and win the most hard-fought and complex coverage cases, he has also demonstrated an ability to find creative, alternative resolutions that are equally satisfying to his clients.  

Jonathan’s clerkship in the Illinois Supreme Court is the backbone of his appellate practice. The knowledge Jonathan obtained clerking for the Honorable Justice Thomas L. Kilbride is invaluable. With a perspective few appellate attorneys have, Jonathan, understands what types of arguments and writing style courts of review find persuasive, and Jonathan uses that unique insight to further his clients’ interests on appeal.  

In addition, Jonathan has experience in representing clients in general litigation defense, including premises liability, negligence, contract disputes, commercial disputes, business torts, professional liability, and product liability. With great enthusiasm and a strong respect for the law, he enjoys the practice of law and the challenges that go with such practice.  

Jonathan is a columnist for the Illinois Defense Counsel Quarterly. He also is an avid Chicago sports fan and enjoys giving back to the community through supporting Illinois Legal Aid Online as a Young Professional Board Member and mentoring law school students and new attorneys.  


  • The John Marshall Law School, J.D. 2013, summa cum laude
  • Illinois State University, B.S. 2006

Judicial Clerkship

  • Justice Thomas L. Kilbride, Illinois Supreme Court

Bar Admissions  

  • Illinois State Bar
  • United States District Court for the Northern District of Illinois

Related Practices

Professional Experience

Professional Affiliations

  • Illinois Legal Aid Online Young Professional Board Member – Membership Chair 2017—18
  • The John Marshall Law School Jobs Advisory Board Committee
  • Illinois Association of Defense Trial Counsel

Articles and Presentations


Federman Elected to Co-Chair Illinois Legal Aid Online Young Professional Board

  Jonathan Federman, was recently elected to a two-year term as a co-chair to the Illinois Legal Aid Online Young Professional Board. ILAO is an organization that provides online and digital resources to lower barriers to the law so that people can understand their legal options, make informed decisions, and figure out how to navigate ...

January 2020 | Firm News

Pretzel Attorneys and Staff Participate in Race Judicata

  Pretzel & Stouffer attorneys and staff, David Bennett, Donald Eckler, Jonathan Federman, Quinn Donnelly, Aimee Alvarez, Alex Beehler, Caitlin Donohue, Scott Howie, Kelly Kono, Mary Norris, Paula Villela, and Calvin Townsend, ran in Race Judicata last night. The 5K race benefits Chicago Volunteer Legal Services.    

September 2019 | Community

Jonathan Federman Speaks at Annual Sommer Foundation Reception

Pretzel & Stouffer attorney, Jonathan Federman, recently spoke at the 2019 Sommer Foundation Annual Reception. The Sommer Foundation provides college scholarships to recent high school graduates who have lost a parent. As a former recipient of a Sommer Foundation scholarship, Jonathan shared his story with the 2019 recipients and the donors who make it possible. ...

July 2019 | Community

Pretzel & Stouffer Attorneys Appointed Columnists for IDC Quarterly

Paula Villela and Jonathan Federman have been appointed to be the Evidence and Practice Tips columnists for the Illinois Association of Defense Counsel Quarterly (IDC). They join Scott Howie (Appellate Practice Corner) and Donald Eckler (Civil Practice and Procedure) as columnists for this excellent publication.

July 2019 | Firm News


Significant Victory for Insurers by Pretzel & Stouffer Before Illinois Supreme Court

  In a significant victory for the insurance industry, Pretzel & Stouffer attorneys, Robert Chemers and Jonathan Federman, prevailed today for an insurer in the Supreme Court of Illinois. The court issued its opinion this morning reversing the trial court and the Illinois Appellate Court, Fifth District, and directing the trial court to enter judgment ...

January 2020

Wisconsin Motion for Judgment Victory Against Pro Se Plaintiff

Robert Chemers and Jonathan Federman, recently obtained a summary judgment in a 39-page Order for an Illinois professional liability insurer in Milwaukee County, Wisconsin. The pro se plaintiff filed a direct action suit against the insurer and several attorneys and law firms. The Court held, among other things, that the insurer did not insure any ...

October 2019

Pretzel & Stouffer Attorneys Obtain Two Summary Judgments in One Day for Insurers

Two motions for summary judgment granted for two clients in two counties on one day.  Donald Eckler, Matthew Ligda, and Jonathan Federman obtained summary judgment for two insurers on a claim of bad faith in one case and an alleged violation of the Consumer Fraud Act in another. The bad faith case arose out of ...

July 2019