Kirk Watkins


[email protected]

Phone: (312) 360-6853

Fax: (312) 360-6520

If you can dream—and not make dreams your master; If you can think—and not make thoughts your aim; If you can meet with Triumph and Disaster and treat those two impostors just the same.

- Rudyard Kipling



Kirk Watkins is a Partner in the Litigation Practice Group.

Kirk has a broad range of experience in all phases of complex commercial litigation, from pre-suit investigation and discovery management to dispositive motion and trial practice all the way up to appeals. In recent years, Kirk has represented clients at multi-week bench and jury trials in both state and federal court in disputes ranging from commercial sales and online taxation to director and officer liability. Kirk generally represents businesses and individuals in litigation and arbitration relating to contract and franchise disputes, real estate and construction disputes, the Uniform Commercial Code, complex class actions, trade secrets, non-compete and non-solicitation agreements, pharmaceutical patents, administrative law, and post-closing, shareholder, and fiduciary liability matters.

In addition to his trial and dispute resolution experience, Kirk has conducted internal corporate investigations and advised clients facing investigations before the Securities and Exchange Commission (SEC) and other governmental bodies.

Prior to joining Freeborn, Kirk was an Associate in the Chicago office of McDermott Will & Emery LLP in both the Trial and White-Collar & Securities Defense Groups. While in law school, Kirk served as a judicial extern to Magistrate Judge Morton Denlow in the U.S. District Court for the Northern District of Illinois.

Kirk also maintains an active pro bono practice, and in 2017 received an Award for Excellence in Pro Bono and Public Interest Service from the U.S. District Court for the Northern District of Illinois and the Chicago Chapter of the Federal Bar Association in connection with his representation of a Stateville inmate in a federal civil rights case.

Representative Matters

Representative Matters

  • Obtained multi-million dollar verdict for national steel processor following three-week jury trial in a dispute with a customer over a long-term supply agreement.

  • Successfully defended e-commerce company at two-week bench trial and subsequent appeal to state supreme court regarding applicability of state and local taxes to online transactions.

  • Represented a corporate director and shareholder in a three-month federal court bench trial in a breach of contract and fiduciary duty matter brought by the corporation’s bankruptcy trustee and seeking over $500 million in damages

  • Represents numerous multinational medical device and pharmaceutical companies in defending claims regarding alleged trade secret and patent infringement.

  • Conducted an internal investigation of a real estate investment company in connection with shareholder derivative demands alleging accounting fraud and conflict-of-interest issues. 

  • Defended an independent bank trustee of various company pension and “top hat” plans in multiple ERISA class actions, each alleging over $200 million in damages. 

  • Represented an investment advisory firm and associated broker-dealer in an SEC investigation and series of related lawsuits arising from the alleged theft of $15 million by a former associated person.

  • Defended several manufacturing companies in separate class actions brought by former union employees seeking to enjoin the companies from making changes to post-retirement healthcare benefits. 





  • “The Mandatory Initial Discovery Pilot (MIDP) in the Northern District of Illinois,” Freeborn’s Powerhouse Points (Spring 2019)
  • Co-Author, "U.S. Supreme Court Will Review the Sixth Circuit's Yard-Man Inference that Retiree Health Insurance Benefits are Vested," Bender's Labor and Employment Bulletin (July 2014).
  • Co-Author, "A Dramatic Change in Multiple Damage Calculations Under the False Claims Act," BNA Federal Contracts Report (June 25, 2013).