Jonathan Schwartz


Chicago, IL
D (773) 389-6440


J.D., University of Illinois College of Law, magna cum laude, 2005

B.A., George Washington University, Elliot School of International Affairs, 2002


Jonathan L. Schwartz is a Partner and Office Co-Chair in Freeman Mathis & Gary’s Chicago office and is Vice-Chair of the firm’s Insurance Coverage and Extra-Contractual Liability national practice section. Mr. Schwartz is also Co-Chair of the firm's Midwest Coverage practice team. He is an experienced litigator whose practices focuses on insurance coverage litigation and counseling across many product lines, including primary and excess commercial general liability, commercial and personal property, business auto and cargo liability, professional liability and errors and omissions (E&O), directors and officers (D&O) liability, cyber, municipal and law enforcement liability, employer’s liability, and employment practices liability insurance policies. A mainstay of Mr. Schwartz’s practice is extracontractual actions against insurers, and with a nationwide focus, his clients include myriad property and casualty insurers from coast to coast.

In addition to his insurance coverage work, Jonathan’s extensive experience includes defending media liability and intellectual property litigation involving trademark infringement, copyright infringement, patent infringement, trade secret misappropriation, consumer and employee privacy, and right of publicity disputes.  Jonathan also regularly defends E&O claims against insurance agents and brokers.

Jonathan has experience in data privacy litigation arising from data security incidents, including data breach class actions and commercial disputes involving managed service providers. He also defends Web businesses who are sued for using data-tracking tools on their Web sites, such as Meta Pixel.  

As a former staff attorney at the Illinois Appellate Court, Mr. Schwartz brings a significant understanding of appellate strategy and the appeals process to all of the work, and frequently represents and counsels clients in appellate matters. He has handled more than 35 appeals throughout his time in private practice.

Mr. Schwartz’s background also includes working as in-house counsel at a captive coverage firm for a major insurance company. This experience provides him with an insider’s perspective and specialized knowledge of performance expectations and the intricacies of the insurer-insured relationship.

A prolific speaker and writer on recent developments affecting the insurance industry, Mr. Schwartz frequently authors articles for publications such as Law360, New Appleman on Insurance, and DRI’s The Voice, For the Defense, and In-House Defense Quarterly. He is often quoted by Law360 on nationwide insurance law issues. He was the regular host of an insurance law podcast.

Mr. Schwartz is currently the Chair of DRI’s Insurance Law Committee and has been a strong advocate of DRI since joining in 2007.

When done for the day practicing law, Mr. Schwartz is a dad to two young boys, who he teaches the violin. Mr. Schwartz is also a lifelong Chicago Bulls and Chicago Cubs fan and regular attendee of theatrical productions throughout the Chicagoland area.

Bar Admissions




State Bar of Wisconsin

U.S. Court of Appeals 4th Circuit

U.S. Court of Appeals 6th Circuit

U.S. Court of Appeals 7th Circuit

U.S. Court of Appeals 8th Circuit

U.S. District Court for the District of Colorado

U.S. District Court for the District of Massachusetts

U.S. District Court for the District of North Dakota

U.S. District Court for the Eastern and Western Districts of Michigan

U.S. District Court for the Eastern District of Missouri

U.S. District Court for the Northern, Central, and Southern Districts of Illinois

U.S. District Court for the Western District of Tennessee

U.S. District Court Northern District of Ohio

U.S. District Courts for the Eastern and Western Districts of Wisconsin

Publications & Engagements

“The Limits of Fine Print: What Lawsuits Against Gentleman’s Clubs Tell Us About Marketing Risks and Coverage Exclusions”(Co-Author), DRI’s For the Defense, April 2022 

“Regulatory Estoppel Does Not Invalidate the Virus Exclusion” (Co-Author), Law360, July 1, 2020

“Ill. Insurance Coverage Cases From 2019 Settle Key Questions,” (Co-Author), Law360, December 19, 2019

Insurance Policy Rescission Compendium (Co-Editor in Chief), DRI, March 2019

“Will You Dance With Me?: An Insurer’s Duty to Initiate Settlement Negotiations,” DRI’s The Voice, April 11, 2018

“Illinois Biometric Privacy Suits Bring Insurance Questions,” Law360, November 17, 2017

“The Modern Fraudster: How Courts Are Responding to Social Engineering Fraud,” Insurance Journal, November 6, 2017

“You Better Pay Up! … I Think?  Insurers’ Right to Sue Retained Defense Counsel,” DRI’s For the Defense, October 2017

“One Bad Apple in Wisconsin Pharmacal Co. v. Nebraska Cultures of California” (Parts One and Two), Wisconsin Law Journal, April 12 and May 8, 2017

“Blurred Lines: Insurers Now Face Increasingly Draconian Consequences for Breaching Their Duty to Defend,” Mealey’s Emerging Insurance Disputes, January 21, 2016

“Notable Illinois Insurance Coverage Decisions In 2015,” Law360, December 23, 2015

“Adapting ‘Professional Services’ For The 21st Century,” Law360, November 3, 2015

“Is Cybersecurity Right for Your Law Firm?,” DRI For the Defense, October 2015

“EPLI Carriers Beware the Rising Tide of FCRA Background Check Class Actions,” InsideCounsel, June 11, 2015

“Sony’s Interview Quagmire: A Watershed Moment for Cyberinsurance,” DRI In-House Defense Quarterly, Spring 2015

“How to Maintain a ‘Sterling’ Reputation With Your Clients: What You Need to Know About CGL Coverage for Unauthorized Recording Claims,” Mealey’s Emerging Insurance Disputes, February 5, 2015

“The Case of the Missing Insured: A Tricky Variation On the Consent to Settle,” Westlaw Journal Insurance Coverage, January 30, 2014

“Settlement Wars: Episode 2—The Frank’s Casing/Blue Ridge Saga Continues,” DRI Covered Events, December 22, 2014

“Swift Distribution as the California Supreme Court’s Commencement Speech: Is the Ruling the First Day of the Rest of the Disparagement Offense’s Life?” Mealey’s Emerging Insurance Disputes, August 7, 2014

“Blocking Coverage From the Anti-Aggregation Rule,”Law360, July 14, 2014

Co-Editor-in-Chief and Contributor, DRI Personal and Advertising Injury Coverage Compendium, 2014

“Class Clown, Most Likely To Succeed, Biggest Flirt: How High School Yearbook Superlatives Can Influence Coverage for Implied Disparagement Claims,” New Appleman on Insurance: Current Critical Issues in Insurance Law, Winter 2013

“The Shawshank Redemption Reimagined: The Contours of Malicious Prosecution and False Imprisonment,” For the Defense, May 2011


Defense Research Institute

Insurance Law Committee: Vice Chair 2020 – 2022 , Chair 2022- 2024

Insurance Industry Advisory Board: Chair, 2016-2020

DRI Insurance Roundtable: Chair, 2019; Vice Chair, 2018

Insurance Coverage Practice Symposium: Chair, December 2014

Insurance Coverage and Claims Institute: Vice Chair, April 2014

Insurance Law Committee’s Advertising Injury and Personal Injury Subcommittee: Chair, 2011–15

Insurance Law Committee Steering Committee, 2010 to present

State Bar of Wisconsin

Awards and Recognition

  •  2023-2024 edition of The Best Lawyers in America®
  • Martindale Hubbell Peer Review Rating AV
  • Best Lawyers in America, Insurance Law, 2018-2022
  • Illinois Super Lawyers, Insurance Coverage, 2016-2022
  • Leading Lawyers, Emerging Lawyer, Insurance, Insurance Coverage, and Reinsurance Law, 2018-Present
Classes/Seminars Taught

“Permissive Use” with Angela Kassube and Greg Dorenkamp, PLRB Claim Conference 2023

“Autonomous Vehicles” with Josh Ferguson, Ed Solensky, and Josh Harrington, FMG Oct 2022 Webinar

Oil Spill presentation with Richard Ahn, PLRB Large Loss 2022

“eDiscovery Expectations of Insurers in a Google World” DRI Insurance Roundtable 2021

“Fixing Claim Handling Mistakes” with Jessica Fairweather , PLRB Large Loss 2021

“Limits of Fine Print” with Heather Arias and Kara Thorvaldsen, DRI Annual Meeting 2021

“A Return To Civility” with Judge George Silver and Bill Passanante, DRI Insurance Coverage Practice Symposium Dec 2021

“Law Firm, Interrupted: Business Interruption Claim Strategies for Your Practice, ALI CLE Webinar, September 30, 2020

“Good Faith Claim Handling and Adjustment of Business Interruption Claims in a COVID-19 World”, DRI webinar, August 11, 2020

“A New Twist on “Additional Insured” Issues,” DRI Complex Coverage Forum, Hartford, CT, November 6, 2019

“Expect the Unexpected: Damaged Windows, Unanticipated Claim Expenses, and the Dangers of the Sublimits,” PLRB Large Loss Conference, Nashville, TN, November 26, 2018

“Insurance Policy Rescission: Misrepresentation Found, What Comes Next?” Client Presentation, Chicago, IL, July 25, 2018

“Cyber Claims: Exposures and Adjustments,” PLRB Regional Adjuster Conference, Glendale, AZ, June 26, 2018

“Social Engineering Fraud: Cyber and Crime Coverage,”  Property & Liability Research Bureau 2018 Claim Conference, Orlando, FL, April 17 and 18, 2018

“Policy Recession,” DRI Insurance Coverage and Claims Institute, Chicago, IL, March 22, 2018

“Social Engineering Fraud: Masters of the Mind,” DRI Northeast Regional Claims Conference, Hartford, CT, November 2, 2017

“Ransomware Litigation: Data Breach Notification Issues, Key Jurisdictional Differences, and Cyber Coverage Issues,” ACI’s Data Breach & Privacy Litigation and Enforcement Conference, New York, NY, September 29, 2016

“Ride and House Sharing: Liability Coverage,” Property and Liability Resource Bureau’s Regional Adjusters Conferences 2016

“Presenting Claim Adjuster Witnesses for Deposition in Bad Faith Cases,” Strafford CLE Webinar, January 2016

“Coverage for Privacy Claims,” Property and Liability Resource Bureau (PLRB), Regional Adjusters Conferences 2015

“Emerging Right of Privacy Claims,” PLRB 2015 Claims Conference, Anaheim, CA, March 29- April 1, 2015

“Consideration for Attorney Involvement in Claims Investigations,” PLRB Regional Adjusters Conferences 2014

“Aggregated Statutory Damages in Class Litigation: Leveraging Rule 23 and Due Process Arguments to Defeat Certification,” (Panelist), Strafford CLE Webinar, September 16, 2014

“Discovery Traps for the Unwary in Coverage Cases,” DRI Insurance Coverage Practice Symposium, New York, December 2012

“A Dash of Cumis and a Hint of Peppers: Problems and Pitfalls in the Selection and Retention of Independent Counsel,” DRI Insurance Coverage and Claims Institute, Chicago, April 2011