Matthew T. Connelly


[email protected]

Phone: (312) 360-6534

Fax: (312) 360-6520

"The leading rule for the lawyer ... is diligence. Leave nothing for tomorrow which can be done today." - Abraham Lincoln

At Freeborn, we work tirelessly as a team to achieve our client’s goals. Through our diligence, we ensure that our clients are in the best possible position to address any legal issue they may face.



Matthew Connelly is an Associate in the Litigation Practice Group and a member of the Insurance/Reinsurance Industry Team. Matt has extensive experience litigating a wide range of commercial disputes involving diverse subject matters such as antitrust law, federal RICO claims, securities fraud, breach of fiduciary duty, breach of contract, insurance and reinsurance disputes, common law fraud, negligence, constitutional claims, and commercial lease disputes. Matt has practiced before state and federal courts across the country, as well as private arbitration panels.   

Prior to joining Freeborn, Matt served as a law clerk for the Honorable William J. Bauer of the United States Court of Appeals for the Seventh Circuit. As a law clerk, Matt researched complex legal issues, prepared for oral arguments, and assisted in drafting appellate opinions regarding diverse subjects such as the Americans with Disabilities Act, Title VII of the Civil Rights Act, and the Federal Rules of Civil Procedure.

Representative Matters

Representative Matters

  • Obtained dismissal of a lawsuit in which the plaintiff alleged claims under the federal RICO statute after a real estate development project between the parties did not materialize.

  • Defended client and prevailed on all claims following an arbitration hearing for breach of contract where petitioner sought over $1 billion in damages.

  • Defended client and reached a favorable settlement following the first day of trial in a lawsuit involving claims for breach of a commercial lease where plaintiff sought over $25 million in damages.

  • Obtained dismissal of all claims against our client in one of the largest antitrust lawsuits ever filed in the U.S. District Court for the Northern District of Illinois.

  • Prevailed in a bench trial for breach of contract on behalf of our client after successfully appealing and reversing the trial court’s original order granting the opposing party’s motion for summary judgment.

  • Defended client and reached a favorable settlement in an insurance coverage dispute involving coal ash plants in which the insured sought hundreds of millions of dollars from its insurers due to environmental remediation costs imposed against it by the state. 

  • Represented client in litigating a breach of contract lawsuit arising from the defendant’s breach of the non-compete provisions within the parties’ contract. 

  • Represented a pro bono client in pursuing a civil rights lawsuit arising from an incident that occurred in the Cook County Jail, which resulted in a favorable settlement for the client.

  • Defended corporation and reached favorable settlement in a complex negligence lawsuit in which the plaintiffs sought over $20 million in damages.

Honors & Awards

Honors & Awards

  • The Best Lawyers in America© Ones to Watch - Commercial Litigation, 2023 (cited in multiple years)

Professional Activities

Professional Activities

  • Chicago Bar Association, Judicial Evaluation Committee
  • CARPLS, Associate Board