Representative Matters

Robert Finley's national civil defense and trial practice focuses on serving businesses and insurers in high-value and complex litigation matters involving specialized tort, employment, and healthcare practice areas. Currently, he primarily represents clients in the transportation, technology, and healthcare sectors and has advised businesses across a variety of industries including construction, home services, insurance (life, health, property, and casualty), pharmaceuticals, real estate, retail, and waste management. He has substantial experience handling jury trials, appellate matters, mediations, and arbitration hearings throughout the country, having been admitted pro hac vice in multiple jurisdictions including Connecticut, Massachusetts, New Jersey, Oregon, Pennsylvania, Texas, and Washington D.C.

Robert's clients appreciate his cover-every-detail approach to their legal problems, as well as his aptitude for creativity and adaptability. These differentiating and complimentary attributes yield pragmatic risk and litigation management solutions, helping his clients achieve preferred, financially sound results.

Robert has a wealth of experience in Medicaid third-party liability and Medicare secondary-payer regulatory and administrative matters. He offers elite counsel on recovery and repayment claims to primary payers, and other statutory third parties, under auto, property and casualty, and no-fault policies, as well as workers' compensation insurance plans, involving:

  • conditional payment resolution;
  • Medicare Part C and D recovery claims;
  • future medical settlement considerations;
  • Section 111 reporting monetary penalties;
  • state-administered Medicaid statutory repayment claims; and
  • related compliance matters.

He also handles commercial causes of action between insurers and medical providers based upon breach of contract, fraud, bad faith, and statutory payment laws or plans.

Further, he advises on all aspects of workplace injury cases, including:

  • workers' compensation defense;
  • post-settlement petitions and judgment enforcement actions;
  • subrogation recovery;
  • employers' liability and excess coverage interests;
  • interplay between workers compensation laws; and
  • other non-occupational disability plans.

He has also represented clients in regulatory matters before the Illinois Workers Compensation Insurance Compliance Division.

Robert further represents professional and amateur sports organizations in litigation, business transactions, and organizational matters.

Professional Background

Robert joined Hinshaw in 2003 and became a partner in 2008. He chairs the firm's Social Media for Trial Committee and developed Social Media Intelligence for Trial at Hinshaw & Culbertson (SMITHc) for obtaining and using social media evidence at trial.

While attending DePaul University College of Law, Robert was selected to study abroad at University College Dublin School of Law (Ireland), where he concentrated in comparative and European Union law studies and volunteered with a Dublin-based law firm in its litigation sector.

Prior to pursuing a career in law, Robert worked in the sports radio industry as a producer and reporter covering major spectator events, including the Super Bowl, NBA Finals, Kentucky Derby, U.S. Open Golf Championship, NCAA men's and women's basketball tournaments, and the 1996 Summer Olympics in Atlanta.

Professional Affiliations

  • Defense Association of New York (DANY)
  • Illinois State Bar Association (ISBA)
    • ISBA Health Care Law Section Council, Member 2023 – 2024
    • ISBA Workers' Compensation Law Section Council, Member, 2012 – 2023
    • ISBA Workers' Compensation Law Section Council, Ex-Officio, 2018
    • ISBA Workers' Compensation Law Section Council, Chair, 2017
    • ISBA Workers' Compensation Law Section Council, Vice-Chair, 2016 – 2017
    • ISBA Workers' Compensation Law Section Council, Secretary, 2015 – 2016
  • Evaluation Committee of the Chicago Bar Association, Investigator & Hearing Officer, 2006 – 2011
  • American Bar Association's National Appellate Advocacy Competition and Regional Negotiation Competition, Judge, 2003 – 2011
  • National Medicare Secondary Payor Network

Honors & Awards

  • Recognized by his peers as a "Leading Lawyer" in the areas of: Arts, Entertainment & Sports Law; Personal Injury Defense Law: General; and Workers' Compensation Defense Law, 2019
  • Recognized on the Rising Star list by Illinois Super Lawyers magazine, 2008 – 2010

Representative Matters

Robert's significant decisions include:

  • Secured summary judgment in Bronx Co., NY in favor of motor vehicle operator, who was planning to make a U-turn, yet came to a complete stop with turn signal engaged prior to suddenly being struck in the rear by co-defendant's vehicle.
  • Achieved dismissal with prejudice in favor of third party administrator where patient agreed to irrevocably assign to medical provider the right to collect medical service charges and statutory interest because the State's workers compensation laws expressly prohibit such assignment and the medical provider's claims failed to satisfy any narrow anti-assignment exceptions.
  • Successfully defended motor vehicle operator obtaining summary judgment in Queens Co., NY against plaintiff rear-seat passenger where operator's vehicle was struck in the rear by co-defendant because plaintiff and co-defendant both failed to provide non-negligent explanation under circumstances for collision.
  • Obtained summary judgment in Cook County, IL for driver against plaintiff bicyclist, where co-defendant, driver's rear seat passenger, opened the vehicle door on the side available to plaintiff because, although driver mumbled, "OK...Go ahead," the co-defendant did not hear or understand the driver prior to knowingly interfering with plaintiff's path of travel in a marked bike lane, and mere status as a driver does not create a duty for opening doors under state vehicle code.
  • Obtained summary judgment in Cook County, IL for driver against two rear-seat passenger plaintiffs, where co-defendant driver, while experiencing bipolar disorder hallucinations, ignored red traffic control signals at an excessive rate of speed, because co-defendants actions were unforeseeable, driver nevertheless acted reasonably under the unexpected circumstances, and no evidence could ever support finding the driver as proximate cause of these plaintiffs injuries.
  • Successfully defended workers compensation insurance pool and its insured home builder denying former employee's claims to increased disability, lifetime total disability, and medical expenses. Appellate court affirmed decision of Commission.
  • Consulting subject matter expert for Applicable Plan successfully disputing Medicare conditional payment claim by Centers for Medicare and Medicaid Services (CMS) resulting in CMS reconsidering and withdrawing its claim in full at administrative level.
  • Successfully defended workers compensation insurer and its insured in a case of first impression against medical provider's quasi-contractual claim based on pre-certification letter for surgical procedure. Appellate Court reversed trial court which erred finding unambiguous promise to pay an amount greater than final award of Illinois Workers Compensation Commission. plaintiffs' writ denied by Illinois Supreme Court.    
  • Reported decision from Illinois Appellate Court affirming trial court's 2-619 dismissal of plaintiff's Motion to Enforce Judgment as premature due to pending corollary proceeding on administrative review.

  • Resolved post-settlement bad faith petition by obtaining favorable advisory opinion from Centers for Medicare & Medicaid Services (CMS) permitting use of allocated Medicare settlement funds to pay for treatment incurred by beneficiary during period after final State commission settlement order but before Federal agency completed its review proceedings.
  • Reported decision from Illinois appellate court on an employer's liability for total disability benefits where there is evidence the employee/beneficiary is working in a reasonably stable labor market.

  • Obtained favorable post-trial relief in federal district court after jury's itemized verdict finding defendant trucking company liable to Medicare-eligible plaintiff for past and future medical expenses totaling $219,375. Chief Judge granted defendants' Post-Trial Motion on Medicare Secondary Payer issues, ordering judgment for past and future medical expenses payable to court clerk and conditioning release of funds on adequate documentation from Centers for Medicare & Medicaid Services (CMS).
  • Successfully defended motor vehicle case in Baltimore, Maryland where company manager operating company car for personal reasons on an interstate highway, in excess of the speed limit, unsuccessfully changed lanes at the exit ramp. plaintiff, an unrestrained backseat passenger, was directing the driver on where to go. The car flipped over several times, ejecting plaintiff who suffered multiple thoracic and lumbar spinal fractures and herniated disks. plaintiff demanded $750,000. The jury was instructed plaintiff's failure to wear a seat belt could not be used in determining if she was contributorily negligent. Jury returned special verdict finding both defendant driver negligent and plaintiff contributorily negligent. However, since Maryland is one of three states following the "contributory negligence is a complete bar" rule, plaintiff recovered nothing.
  • Successfully defended national pest control company against civil trespass case in Santa Fe, New Mexico where a residential service technician applied pesticide to the house and adjacent land of property owner who not only was not a customer.  Also at the time of the pesticide application the property owner was totally disabled as a result of pre-existing workplace chemical exposure to same pesticides. Jury rejected plaintiff's $890,000 case based on lack of proximate cause.
  • Successfully defended motor vehicle case in rural Pennsylvania where company truck driver pulled out from a stop sign in front of the plaintiff motorcyclist ascending the crest of the roadway resulting in knee and hip injuries. Jury rejected plaintiff's claim of negligence and returned a verdict in favor of the defendant driver. State appellate court reinstated jury verdict for the defense and vacated trial court's judgement order notwithstanding verdict.
  • Case of first impression developing an analytical framework for applying American Medical Association impairment guides under Illinois Workers' Compensation Act following 2011 reforms.
  • Case of first impression regarding the application of the state's medical fee schedule, and limits on construction worker's overtime pay as a basis for benefit rate calculations.
  • Successfully reversed workers' compensation administrative decision finding permanent, total disability and subsequently dismissed opponent's appeal on jurisdictional grounds.


Robert is frequently invited to speak on defense litigation, Medicaid and Medicare reimbursement, and workers' compensation topics. He has instructed at Hinshaw University, the firm's nationwide attorney training and education program, on taking and defending depositions, negotiations, and settlement releases.

His recent presentations include:

  • Co-Presenter, "Don't Be the Villain – False Claims Act," 2023 National Medicare Secondary Payer Network (MSPN) Annual Educational Conference, Baltimore, Maryland November 9, 2023
  • Co-Presenter, "Personal Injury Settlement Strategies: Reckoning With Medicaid Reimbursement From Payments for Future Medical Care," Strafford, Webinar, November 8, 2023
  • Co-Presenter, "A New Threat: Beware of Medicaid Liens in Your Premises Liability Claims," 2023 CLM Annual Conference, Tampa, Florida, March 30, 2023
  • "Assess Variations Between Different State Medicaid Lien Laws," RISE Medicare Secondary Payer (MSP) World 2023, Tampa, Florida, March 2, 2023
  • "What's Up Their Sleeve? The Future of LMSAs," 2022 National Medicare Secondary Payer Network (MSPN) Annual Educational Conference, Hanover, Maryland, September 21, 2022
  • "Intro to SCOTUS Cases on Medicaid Liens," RISE 6th Annual Medicare Secondary Payer Conditional Payment Forum, Virtual Event, July 11, 2022
  • Co-Presenter, "Employers and Carriers Beware: Claims with Medicaid Recipients Need Special Attention," 2022 CLM Workers Compensation and Retail, Restaurant & Hospitality Conference, Chicago, Illinois, May 20, 2022
  • "Reporting and Reimbursement: Handling Conditional Payments in the Defense of Liability Plans under MSP," 7th Annual RISE Medicare Secondary Payer Master Class, Washington, D.C., February 25, 2022
  • Co-Presenter, "Analyze the Pre-Settlement Conditional Payment Resolution Process," 6th Annual RISE Medicare Secondary Payer Conditional Payment Forum, Virtual Event, July 27, 2021
  • Co-Presenter, "Established Strategies for Working with US DOT and US DOJ," 6th Annual RISE Medicare Secondary Payer Master Class, Virtual Event, February 10, 2021
  • Co-Presenter, "Conditional Payment from Conception to Completion: Requesting Redetermination of Medicare's Demand for Reimbursement of Conditional Payments," 5th Annual RISE Medicare Secondary Payer Conditional Payment Forum, Virtual Event, July 28, 2020
  •  Co-Presenter, "CMS Notice of Proposed Rules Part 2: An Analysis of the Mandatory Reporting Proposed Civil Money Penalty Regulations," 4th Annual RISE Medicare Secondary Payer Conditional Payment Forum, Virtual Event, July 27, 2020
  • Panelist, "Saving $1,000/Day — Avoiding Mandatory Reporting Civil Money Penalties," 2020 CLM Workers Compensation and Retail, Restaurant & Hospitality Conference, June 18, 2020
  • Co-Presenter, "Medicare Set-Asides: An Update on Liability Medicare Set-Asides," 5th Annual RISE Medicare Secondary Payer Master Class, Jacksonville, Florida, February 4, 2020
  • Co-Presenter, "Conditional Payments: Best Practices for Resolving Conditional Payments Post-Settlement with the Benefits Coordination and Recovery Center (BCRC)," 5th Annual RISE Medicare Secondary Payer Master Class, Jacksonville, Florida, February 4, 2020
  • "Mandatory Reporting: Efficient Reporting of Total Payment Obligation to Claimant (TPOC) in Liability, No Fault, and Workers Compensation," 5th Annual RISE Medicare Secondary Payer Master Class, Jacksonville, Florida, February 3, 2020
  • Panelist, "Leveraging Settlement with MSAs in Mediation," National Alliance of Medicare Set-Aside Professionals (NAMSAP) 2019 Educational Conference, Baltimore, Maryland, September 18, 2019
  • "Medicaid Third Party Liability: Resolving State Agency and MCO Claims," RISE! 3rd Annual Medicare Secondary Payer Conditional Payment Forum, Washington D.C., August 27, 2019
  • "Medicare Set-Asides in Personal Injury ‒ New Developments," National Business Institute, Teleconference, June 5, 2019
  • "Technology & Transportation: Legal Issues in App-Based Ride Sharing," Hinshaw University, Chicago, Illinois, May 29, 2019
  • "Mitigation of Medicare Settlement Risk and Costs Through Clinical and Pharmacological Controls," 2019 CLM Workers Compensation Conference, Chicago, Illinois, May 22, 2019
  • Co-Presenter, "Medicare Advantage Plan Update – Trends and Case Law," 4th Annual RISE! Medicare Secondary Payer Master Class, The Essential Guide to the Latest Developments in Mandatory Insurer Reporting, Conditional Payments, Medicare Set-Asides and Medicaid Secondary Payer, Miami, Florida, February 27, 2019
  • Co-Presenter, "Advantages and Disadvantages of Professional Administration," 4th Annual RISE! Medicare Secondary Payer Master Class, The Essential Guide to the Latest Developments in Mandatory Insurer Reporting, Conditional Payments, Medicare Set-Asides and Medicaid Secondary Payer, Miami, Florida, February 27, 2019


Robert created Hinshaw's Mr. Medicare: Rx for Compliance publication, which provides resources, analysis, and perspective on Medicare Secondary Payer laws.

Relying on his extensive knowledge and experience with Medicare and Medicaid compliance, Robert also contributed posts for the Flagship Services Group blog, including:

  • "Early Observations on Michigan's New Auto No Fault Laws," January 4, 2021
  • "Florida Medicaid Third Party Liability Act Survives 11th Circuit Challenge," November 17, 2020
  • "Early Takeways from CRC NGHP Applicable Plan Appeals Webinar," September 29, 2020
  • "Dog Days of Summer," August 24, 2020
  • "Decision Point: Z Code Conundrums," July 20, 2020
  • "Tea Leaves and Time Bombs," July 2, 2020
  • "Summer School: Briefing Key Cases in 2020," June 23, 2020
  • "Chicken Soup for Section 111: Boiling Down the Public Comments on Proposed Civil Money Penalties," June 1, 2020
  • "Opportunity for Improvement," May 5, 2020

Robert's other publications include:

  • "To Be or Not to Be an Employee?," Workers Compensation Law, Illinois State Bar Association, Vol. 60, No. 2, November 2022
  • "50 State Primer on Medicaid Recovery Laws," Hinshaw's On The Law Series, Third Edition, September 2022; Second Edition, August 2019; First Edition, December 2016
  • "Mind the Gap: Maroney's Rule 23 Caution on Causal Connection," Workers Compensation Law, Illinois State Bar Association, Vol. 58., No. 5, May 2021
  • "Seeing Double: The Inextricably Intertwined Case(s) of Mr. Centeno a/k/a Mr. Morales," Workers Compensation Law, Illinois State Bar Association, Vol. 57., No. 6, May 2020

Community/Civic Activities

Robert devotes his personal time to a number of vital organizations, including:

  • Chicago Mission Hockey Club
  • DePaul College Prep
  • Galway, Ireland Committee (Chicago Sister Cities International)
  • Hockey Players In Business
  • Irish American Heritage Center
  • Old St. Patrick's Church of Chicago

Robert was also a member of Hinshaw's Host Committee for the 2018 Reception and Luncheon honoring Ireland's 13th Prime Minister, Mr. Enda Kenny.

J.D., DePaul University College of Law, 2001

B.A., Marquette University, 1995