Matthew Maloney

Chicago, Illinois

Matthew Maloney is a shareholder at DeBofsky Law.  He 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 Law, 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


“Could Not Be Happier”

Thank You for all of your help. I could not be happier with you or the team at DeBofsky.
Your professionalism and prompt responses to inquiries have made me feel so much
better knowing all of you are on my side. It means more to me than you could ever realize.



  • 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

  • Scanlon v. Life Ins. Co. of N. Am., 81 F.4th 672 (7th Cir. 2023)
  • Robinson v. Aetna Life Ins. Co., 2023 U.S. Dist. LEXIS 26452 (N.D. Ill. Feb. 16, 2023)
  • Braun v. Unum Life Ins. Co. of Am., 2022 U.S. Dist. LEXIS 226701 (N.D. Ill. Dec. 16, 2022)
  • 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., 2020 WL 13519237 (N.D. Ill. Mar. 20, 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 Organizations

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

Past Employment

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


  • English
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