Mr. Tomashefsky’s practice is focused on complex litigation, including intellectual property, construction, and bankruptcy.  Mr. Tomashefsky has represented major record labels and recording artists, the technology transfer office of a major university, developers/owners of real-estate projects, high-tech engineering firms, a major telecommunications firm, a hotel/motel chain, and several large health insurance companies in disputes involving construction defects, construction finance, copyright and patent infringement, breaches of contract, and insolvency.  In addition, Mr. Tomashefsky has represented several not-for-profit organizations in disputes with government agencies and in organizational matters.  Mr. Tomashefsky’s experience includes jury and bench trials, appeals, arbitrations, and negotiated settlements.  Before attending law school, Mr. Tomashefsky produced and promoted blues and jazz albums for a Chicago record label.

Key Professional Accomplishments

Mr. Tomashefsky has been listed in Illinois Super Lawyers since 2005 and has had an av rating from Martindale Hubbell since 1992.


Mr. Tomashefsky is the author of several articles and presentations related to complex litigation strategy and skills, including:

  • Helpful Rules for Writing and Drafting Helpful Briefs (16th ed. 2008)
  • Bridge the Gap for Newly Admitted Attorneys (PLI 2006)
  • Federal Trial Practice (IICLE 1995)
  • Course of Study on Lender Liability (ALI-ABA 1992)
  • We Do Have an Adversary System, Don’t We? (Litigation Magazine 1991)
  • Antipsychotic Drugs & Fitness to Stand Trial (University of Chicago Law Review 1985)

Professional, Business and Civic Affiliations

  • Illinois Supreme Court
  • United States Court of Appeals for the Second Circuit
  • United States Court of Appeals for the Sixth Circuit
  • United States Court of Appeals for the Seventh Circuit
  • United States District Court for the Northern District of Illinois (including Trial Bar)
  • United States District Court for the Central District of Illinois
  • United States District Court for the Southern District of Illinois
  • Member, American Bar Association (Litigation and Intellectual Property Sections)
  • Member and Past President, Chicago Council of Lawyers
  • Past Chairman, Sargent Shriver National Center on Poverty Law
  • Past Chairman, Chicago Area Project
  • Past President, The Caxton Club


Mr. Tomashefsky received his Juris Doctor degree cum laude in 1985 from the University of Chicago Law School, where he was Articles Editor of the University of Chicago Law Review and a member of the Order of the Coif. He received his Bachelor of Arts degree cum laude in 1972 from Harvard University. Following his graduation from law school, he served as law clerk to the Honorable Milton I. Shadur of the United States District Court for the Northern District of Illinois.