John M. O'Bryan


[email protected]

Phone: (312) 360-6580

Fax: (312) 360-6520

Freeborn is an effective law firm because it is creative, both with respect to representing clients and managing the firm’s people.



John M. O'Bryan is a Partner in the Litigation Practice Group.

John focuses his practice in Insurance Coverage, Reinsurance, Unfair Competition and Commercial Litigation. In addition to his extensive litigation experience in state and federal trial and appellate courts throughout the U.S., John has arbitrated to award investment disputes before the American Arbitration Association, the London Court of International Arbitration and the FINRA Dispute Resolution Center, as well as numerous insurance/reinsurance disputes before ad hoc panels.

Prior to entering the legal profession, John worked for the Smith Richardson Foundation in New York City, and the European Journalism Network in Prague, where he helped young journalists in Central and Eastern Europe publish independent newspapers.

Representative Matters

Representative Matters

  • Lead outside counsel for P&C re/insurer with respect to COVID-19 claims.

  • Represent several life insurers/reinsurers in YRT reinsurance rate disputes.

  • Represent P&C excess insurer in multimillion dollar subrogation/insurance allocation litigation between manufacturer and its vendor and their various insurers concerning major loss and related settlement.

  • Tried Lanham Act case in Federal Court for the Northern District of California on behalf of company accused of unlawfully poaching competitor’s customers via deceptive sales tactics. Trial settled after the close of evidence with client paying no damages.

  • Obtained rescission of quota share treaty on behalf of reinsurer for cedent's fraudulent accounting and reporting of historical loss ratios, resulting in award of $28 million.

  • Represented investors and senior officers in shareholder dispute over control of a Dutch holding company with operations in Poland. Clients maintained control of company with no forced, above-market buyout of dissenting shareholder.

  • Defended Bermuda mutual insurer in arbitration regarding forfeiture of departing member's equity. Client retained former member's equity.

  • Successfully prosecuted claims against municipalities, tax accountants and retailers involved in sales tax/use tax swap arrangements, whereby defendants were diverting a portion of sales tax revenue to themselves by declaring to the taxing authority that out-of-state sales were in-state sales.

  • Represented engineering company in federal criminal investigation into violation of U.S. sanctions with respect to the building of a gas plant in Iran.

  • Won several contempt proceedings in Federal courts in California and Florida in which clients were accused of violating stipulated injunctions prohibiting unfair competition and Lanham Act violations.

  • Represented surety in major financial fraud litigation arising out of more than a billion dollars in performance bonds for Enron "round-trip" energy transactions. Case settled after closing arguments for a substantial discount on the bonds.

  • Represented insured warehouse operator that had been denied coverage for millions of dollars in losses arising out of major warehouse fire. Obtained recoveries from insured's primary and excess insurers and insurance broker.

  • Recovered on behalf of a financial institution hundreds of millions of dollars from accountants and insurance managers involved in finite reinsurance scheme.

  • Represented former COO of major Chicago REIT in breach of contract employment dispute with his former employer. Case settled with a substantial payment to the client.

  • Won reinsurance arbitration award for cedent, wherein the panel awarded client $26 million in claims. Wrote and argued appeal in which Second Circuit reinstated an award of 100% of client’s attorney fees for opponent's bad faith conduct.

Honors & Awards

Honors & Awards

  • Illinois Leading Lawyers (multiple years)

Professional Activities

Speaking Engagements

  • Presenter, Association of Insurance & Reinsurance Run-Off Companies (AIRROC), 2021 Summer Membership Meeting (July 2021).
  • Presenter, Negotiation Workshop, Brokers & Reinsurance Markets Association's Committee Rendezvous (April 2019). 









  • "COVID-19 Claims: Single Or Multiple Occurrences?," Mealey's Litigation Report: Reinsurance, June 5, 2020.