Dennis M. Dolan

Dennis joined Litchfield Cavo LLP in 2001 and became a partner in 2006. His practice involves insurance coverage and bad faith litigation and providing insurance coverage advice. His experience encompasses a wide array of claims and all types of insurance including general liability, first-party property, and errors and omissions policies -- including directors and officers liability and public sector liability policies. Before entering private practice, Dennis was employed in Wausau Insurance Company’s environmental claim unit. He gained extensive insurance coverage training over four and one-half years handling claims and declaratory judgment actions involving matters ranging in size from homeowner claims up to multi-million dollar Superfund clean-ups.  His claim background gives him a unique perspective and ability to relate to the needs of his insurer clients.  His private practice has involved extensive work in coverage issues related to environmental and asbestos liabilities.  However, he also has significant experience in many areas of insurance coverage including construction defect claims, directors and officers liability, and public sector liability as well as a wide range of general liability matters.


  • Wayne State University, JD, 1995; cum laude
  • University of Notre Dame, BS, 1989; biology


  • Illinois
  • Indiana
  • United States District Courts: Northern District of Illinois, Central District of Illinois, Southern District of Illinois,  Northern District of Indiana, Southern District of Indiana, Eastern District of Michigan, Western District of Michigan, District of Nebraska, District of North Dakota, Western District of Texas
  • United States Courts of Appeal: Seventh Circuit, Eighth Circuit

Professional Activities

  • American Bar Association


  • "Erosion of Attorney-Client Privilege in Insurance Coverage Disputes," Tort Trial & Insurance Practices Sections Seminar, 2008

Representative Reported Cases

  • Berry v. Travelers Indemnity Company of America, 770 F.3d 591 (7th Cir. 2014)
  • Royal Indemnity Co. v. Apex Oil Company, Inc., 511 F.3d 788 (8th Cir. 2008)
  • St. Paul Fire and Marine Ins. Co. v. City of Zion, et al., 2014 IL.App. (2d) 131312, 18 N.E. 3d 193 (2d Dist. Ill.)
  • Lemko Corp. v. Federal Ins. Co., 70 F Supp. 3d 905 (N.D. Ill. 2014)
  • The Cincinnati Ins. Co. v. Northridge Builders, Inc., 2015 WL 4099815 (N.D.Ill.)
  • The Cincinnati Ins. Co. v. Maintenance Dynamics, Inc., 2013 WL 350080 (N.D.Ind.)
  • The Cincinnati Ins. Co. v. Boller Construction, Inc., 2006 WL 695459 (N.D.Ill.)