Matthew Maloney

Chicago, Illinois

Attorney Matthew Maloney focuses his practice on the representation of individuals in disability and healthcare benefit disputes. Since joining the firm in 2017, Maloney has already achieved notable victories for healthcare claimants in Alice F. v. Health Care Serv. Corp., 367 F. Supp. 3d 817 (N.D. Ill. 2019) and Dominic W. v. N. Trust Co. Emp. Welfare Benefit Plan, 392 F. Supp. 3d 907 (N.D. Ill. 2019), both of which involved claims seeking coverage for residential mental health treatment. He has also successfully overturned many long-term disability benefit denials.

Prior to joining DeBofsky Sherman Casciari Reynolds P.C., Maloney graduated cum laude from The John Marshall Law School in 2017 with certificates of concentration in Health Law and Alternative Dispute Resolution. While in law school, Maloney was a member of the Law Review and served as an Executive Board member of the Moot Court Honors Program. He also competed on the school’s National Moot Court Competition team and won the school’s Herzog Moot Court Competition, in addition to acting as a certified mediator for small claims in state court. Maloney further worked as a judicial extern for Judge Irwin Solganick in the Circuit Court of Cook County.

Bar Admissions

  • Illinois, 2017
  • U.S. District Court Northern District of Illinois, 2017
  • U.S. Court of Appeals 7th Circuit, 2017


  • The John Marshall Law School, Chicago, Illinois
    • J.D. cum laude – 2017
    • Honors: Law Review, Moot Court Honors Executive Board, Dean’s List
  • St. Norbert College, De Pere, Wisconsin
    • B.A. cum laude – 2014
    • Honors: Pre-Law Certification, Dean’s List
    • Major: Political Science
    • Minor: Communication Studies

Representative Cases

  • Robinson v. Aetna Life Ins. Co., 2021 U.S. Dist. LEXIS 176346 (N.D. Ill. Sept. 15, 2021)
  • Day v. Humana Ins. Co., 335 F.R.D. 181 (N.D. Ill. 2020)
  • Szabo v. Hartford Life and Accident Ins. Co., No. 18-CV-06258 (N.D. Ill. March 10, 2020)
  • Dominic W. v. N. Trust Co. Emp. Welfare Benefit Plan, 392 F. Supp. 3d 907 (N.D. Ill. 2019)
  • Alice F. v. Health Care Serv. Corp., 367 F. Supp. 3d 817 (N.D. Ill. 2019)

Professional Associations & Memberships

  • Center for Conflict Resolution, Certified Mediator
  • American Bar Association
  • Chicago Bar Association

Past Employment Positions

  • DeBofsky, Sherman & Casciari, P.C., Contract Attorney, 2017 – 2018
  • The Law Offices of Michael Bartolic, L.L.C., Law Clerk, 2015 – 2017


  • English
Best Lawyer Badge - DeBofsky 2021-2022

Get Results. Contact Us to Get Started

Our employee benefits and disability insurance attorneys can serve you in Chicago and across the nation. Contact us to get your rights secured.

Contact Matthew