Andy Shapiro is a litigation attorney in Holland & Knight's Chicago office, where he concentrates his practice on assisting carriers and managing general agents with representations and warranties insurance (RWI) claims, insurance coverage counseling and disputes, and complex commercial litigation.

With respect to his RWI practice, Mr. Shapiro counsels clients on a variety of claims, including alleged breaches of representations involving accounts receivables, absence of changes, compliance with laws, financial statements, internal controls, material contracts and customers, and undisclosed liabilities.

Mr. Shapiro also has a broad range of insurance and reinsurance experience involving transactional liability, errors and omissions, cyber, commercial general liability, directors and officers, employment practices liability and commercial property policies. In addition to providing coverage advice, Mr. Shapiro litigates and arbitrates multimillion- and billion-dollar insurance and reinsurance disputes on behalf of insurers, cedents and reinsurers.

In addition, Mr. Shapiro has extensive experience representing corporations, partnerships and individuals in a wide range of commercial disputes before trial and appellate courts and administrative agencies. He represents plaintiffs and defendants in cases involving claims of antitrust price fixing and monopolization, breach of contract, breach of non-compete agreements, employment discrimination, statutory, common law, as well as consumer fraud and breach of fiduciary duty. Mr. Shapiro also represents publicly traded companies in sensitive internal investigations.

Mr. Shapiro has an active pro bono practice and has been honored by The Law Project of the Chicago Coalition for the Homeless for his work. He has represented pro bono clients in homeless shelter accessibility cases, asylum claims, summary suspension hearings, and criminal and civil appeals before the Illinois Appellate Court. In addition, since 2009, Mr. Shapiro has served as an adjunct professor at the Northwestern Pritzker School of Law, where he teaches Pre-Trial Advocacy.

Prior to joining Holland & Knight, Mr. Shapiro was an attorney and co-chair of the RWI practice in the Chicago office of a large national law firm.

Representative Experience

  • Represented the owner of a 38-story office building in connection with a complaint seeking rescission of an agreement to sell the property and building
  • Represented a client in connection with discrimination claims brought by former employees
  • Represented clients in connection with various issues arising from employment contracts and non-compete agreements
  • Represented a client in an action brought by a litigation trust for the benefit of creditors seeking recovery for allegedly illegal dividend distributions
  • Represented a large, direct-to-consumer clothing merchant in an action alleging, inter alia, breach of contract, fraud and copyright infringement against a software provider
  • Represented a developer in construction defect cases

  • Represented an insurer in a more than $1 billion-dollar lawsuit alleging fraud and breach of contract against lenders, which were issued credit insurance policies for hundreds of thousands of home equity loans and lines of credit
  • Represented an insurance company in a dispute with Lloyd's of London syndicates and other insurers concerning coverage for a multimillion-dollar claim under professional indemnity policy
  • Represented a cedent at a hearing relating to the reinsurance of annuity death and income benefits
  • Represented title insurers in a multidistrict litigation (MDL) proceeding in which the insured alleged breach of closing protection letters and sought indemnification in connection with more than 200 opt-out cases
  • Represented an insurance company in dispute with its insurer concerning coverage for a multimillion-dollar claim under a professional liability policy
  • Represented a cedent at hearing relating to loss arising out of a policy's supplementary payments provision
  • Represented a cedent in dispute concerning the number of occurrences in underlying asbestos, silica and priest-abuse claims
  • Represented a cedent in dispute regarding whether third-party administrator expenses were properly ceded as allocated loss adjustment expense
  • Represented a cedent in matter involving reinsurer's claim that finite reinsurance policy should be reformed based on mutual mistake
  • Represented a reinsurer in matter involving the consolidation of arbitrations arising out of multiple treaties

  • Represented a global engineering and construction company in the first consummated merger case tried in an administrative hearing before the Federal Trade Commission (FTC) in more than two decades
  • Represented the marketers of sulfur-based products in an action alleging a conspiracy in the sulfuric acid industry in violation of Section 1 of the Sherman Act
  • Represented corrugated container manufacturers in a class action, and subsequent opt-out litigation, alleging coordinated restrictions on linerboard supply
  • Represented the world-leading producer of decorative surfacing products in a class action alleging price-fixing conspiracy


  • University of Illinois College of Law, J.D., magna cum laude
  • Miami University, B.S.
Bar Admissions/Licenses
  • Illinois
Court Admissions
  • U.S. Court of Appeals for the Third Circuit
  • U.S. Court of Appeals for the Seventh Circuit
  • U.S. District Court for the Northern District of Illinois, Trial Bar
  • U.S. District Court for the Central District of Illinois
  • Law360 Editorial Board Member, Insurance Authority Specialty Lines, 2023-2024
  • Association Internationale de Droit des Assurances (AIDA) Reinsurance and Insurance Arbitration Society (ARIAS-U.S.), Law Committee, 2010-2012
  • Chicago Coalition for the Homeless (CCH), Board of Directors, 2009-2016
  • Insurance Industry Charitable Foundation (IICF), Board of Directors, 2013-2015
  • North Shore School District 112, Superintendent's Citizen Finance and Facilities Committee, 2012-2014
Honors & Awards
  • Advocacy Award, Chicago Coalition for the Homeless Victory Celebration, 2024
  • Illinois Super Lawyers magazine, Business Litigation, 2018-2024
  • Rising Stars, Illinois Super Lawyers magazine, Business Litigation, 2012-2015
  • Illinois Leading Lawyer, Law Bulletin, Commercial Litigation and Insurance, Insurance Coverage & Reinsurance Law, 2018-2022
  • Illinois Emerging Lawyer, Law Bulletin, Commercial Litigation and Insurance, Insurance Coverage & Reinsurance Law, 2016
  • The Best Lawyers in America guide, Antitrust Law, 2019-2023; Commercial Litigation, 2024
  • Martindale-Hubbell AV Preeminent Peer Review Rated

Speaking Engagements