K. James Sullivan

Alongside his skilled teammates, James’s purpose is to provide policyholder-side insurance coverage services to closely held and publicly traded corporate policyholders on a variety of matters, including:

• Litigating insurance policy and bad-faith claims
• Advising clients when buying insurance policies
• Making recommendations about clients' existing insurance programs
• Supporting M&A transactions, including with respect to representations and warranties insurance and due diligence.

James has litigated in many state and federal trial and appellate courts nationwide. He has also served as an expert witness, mediator, and arbitrator for insurance coverage matters.

James is one of 21 Ohio lawyers certified as an Insurance Coverage Law Specialist by the Ohio State Bar Association. He is a member of the American College of Coverage Counsel (ACCC).

James received the 2022 Respected Advocate Award from the Ohio Association of Civil Trial Attorneys (OACTA).

Since 2020, James has been recognized by Chambers USA in Band 1 for his work in Insurance: Policyholder Law in Ohio. Chambers USA has also recognized James at the USA-Nationwide level in Insurance: Dispute Resolution: Policyholder (Band 3).

Clients interviewed by Chambers USA said, "James is the best policyholder insurance coverage attorney I have ever worked with. James is a seasoned insurance recovery lawyer who listens to his clients’ goals and steers disputes to successful conclusions. He is an expert in his field. He is very practical, very clear-eyed, and can really read the situation well. He understands the issues quickly, provides targeted, concise advice on complex issues, and is an outstanding negotiator skilled in working with insurance adjusters and their counsel. He is eager to learn about our business, and that pays dividends in the quality of his work."

Chambers USA researchers noted that "[James] is held in high esteem for his approach to complex recovery claims, which sees him handle a wide range of coverage disputes," and praised James for his "sophisticated and diplomatic approach” to “analyzing situations and getting good results."

James has been selected for the Ohio Super Lawyers’ "Top 100 Attorneys in Ohio" list (2015-2027) and "Top 50 Attorneys in Cleveland" list (2015-2020, 2022-2027). In 2023, Business Today designated James as one of the "Top 10 Most Influential Insurance Lawyers in Ohio." He has also been selected to The Best Lawyers in America^® list since 2017, being named its Cleveland Insurance Law "Lawyer of the Year" in 2018 and 2027.

James joined Calfee in 2001 and was elected Partner in 2010. James serves on the firm's Inclusion & Diversity Committee. He also serves as a formal and informal mentor to other Calfee attorneys.

James has been elected to Calfee's Management Committee each year since 2023.

Honors & Recognitions

• Chambers USA, Insurance: Policyholder, Band 1, Ohio (2020-2026)
• Chambers USA, Insurance: Dispute Resolution: Policyholder, Band 3, USA-Nationwide (2025-2026)
• Ohio Association of Civil Trial Attorneys (OACTA) 2022 Respected Advocate Award
• Ohio Super Lawyers, Insurance Coverage (2014-2027)
  • Top 100 Attorneys in Ohio List (2015-2027)
  • Top 50 Attorneys in Cleveland List (2015-2020, 2022-2027)
• Benchmark Litigation "Litigation Star" – U.S. (National) and Ohio: Insurance Litigation (2022-2026)
• The Best Lawyers in America^® Insurance Law "Lawyer of the Year" in Cleveland (2027, 2018)
• The Best Lawyers in America^®, Commercial Litigation; Insurance Law; Litigation – Insurance (2017-2027)

Education

Ohio State Bar Association Certified Specialist in Insurance Coverage Law, 2016

J.D., University of Virginia School of Law, 2001

B.A., Philosophy, magna cum laude, John Carroll University, 1998

Experience

Insurance Policyholder Recovery and Counseling Services

James has been litigating on behalf of and counseling insurance policyholders on coverage matters since 2004. James’s practice is wholly devoted to representing policyholders.

He has experience with a wide array of insurance policy types, including the following:

• Commercial general liability (CGL) (including for long-tail claims like asbestos and environmental)
• Umbrella
• Excess
• Property
• Business interruption (including business income and extra expense)
• Cyber (first-party loss + third-party liability)
• Directors & officers (D&O)
• Side-A excess
• Difference in conditions (DIC)
• Professional services
• Errors & omissions (E&O)
• Representations and warranties (RWI)
• Tail & nose coverages
• Discontinued operations
• Employment practices (EPL)
• Stop-gap
• Fiduciary/employee benefits
• Trustee
• Captive
• Risk retention group (RRG)
• Pollution legal liability (PLL)
• Environmental liability
• Contingent liability
• Products/completed operations
• Contractor
• Contract liability
• Business credit
• Tax indemnity
• Medical malpractice
• Legal malpractice
• Employed lawyers
• Public entity
• Educators legal liability (ELL)
• Business crime
• Employee theft
• Fidelity bond
• Sexual misconduct & molestation
• Surety
• Liquor
• Fine art
• Aviation
• Warehouse legal liability
• Commercial auto
• Equipment breakdown
• Event cancellation
• Business trip interruption
• Special events
• Parametric/index-based

Representative sample of recent services James has provided to insurance policyholder clients:

• 2026 – Over the past decade-plus, regularly counseling and litigating on behalf of various clients suffering natural disaster-related losses, including from hurricanes, floods, winter storms, power outages, earth movement, and fires.
• 2026 – For nearly two decades, assisting multiple clients, including Fortune 500 health care services and Forbes Global 2000 heavy equipment companies, with design and administration of insurance coverage programs for asbestos claim portfolios.
• 2026 – Since the mid-2010s, regularly advising and litigating on behalf of numerous M&A clients on placement of representations and warranties insurance (RWI) coverage and prosecution of RWI claims totaling tens of millions of dollars.
• 2026 – Advocating insurance and indemnification claims for Berkshire Hathaway portfolio entity pertaining to fatality accident.
• 2026 – Assisting client group’s efforts with bad-faith and insurance coverage claim to protect against underlying $60 million-plus jury award.
• 2025 – Served as a privately hired mediator for insurance coverage dispute involving large fire loss.
• 2023-2026 – Litigating federal insurance lawsuit regarding failure of insurance company to provide coverage for nationwide product recall by publicly traded food manufacturer.
• 2022-2026 – Negotiating multiple property and business interruption losses for a Fortune 500 commercial apparel service company against its insurers that have failed to fully honor their coverage obligations.
• 2017-2026 – Helped company in medical insurance sector administer defense and indemnification claim under primary and excess E&O policies in private and municipal-law class actions that sought a combined nine figures in alleged damages.
• 2024-2025 – Represented university in insurance coverage claims for NCAA concussion litigation.
• 2023-2026 – Litigating federal and state insurance lawsuits on behalf of municipality for a $45 million wrongful imprisonment jury verdict.
• 2020-2026 – Representing religious organization with respect to insurance coverage for multiple third-party lawsuits collectively seeking tens of millions of dollars.
• 2022-2026 – Litigating $6 million-plus insurer bad-faith and breach of contract claim alongside insurance broker malpractice claim on behalf of contract provider of physician and health care services.
• 2017-2025 – Helped New York-based consumer product manufacturer and supplier for top big-box retailers secure millions of dollars of CGL insurance coverage for multiple consumer and municipality class-actions filed nationwide.
• 2024 – Served as a privately hired arbitrator for insurance coverage dispute between medical equipment company and its CGL insurers.
• 2023-2025 – Obtained confidential eight-figure amounts various lines of insurance for defense and indemnification of various third-party claims against Ohio window manufacturer collectively valued at over $50 million.
• 2023-2025 – Counseled Ohio-based construction goods manufacturer regarding insurance coverage for ransomware attack that halted production lines at all 11 worldwide manufacturing facilities, including navigation of high self-insured retention, post-retention coinsurance issues, multiple insurer risk-sharing allocation, and resulting class-action lawsuit.
• 2023 – Assisted Calfee insurance policyholder Partner Matt Chiricosta with Ohio Supreme Court amicus brief for Ohio Manufacturers Association that was joined by 10 of Ohio’s largest manufacturers.
• 2022-2023 – Obtained $110 million federal court judgment with respect to bodily injury and property damage claims against Ohio-based medical sterilization company, with Law360 publication designating the matter as one of most important insurance coverage lawsuits in the U.S.
• 2022 – Served as insurance coverage litigation expert for forensic consultant in lawsuit by insurer regarding that consultant’s services previously performed on the insurer's behalf.
• 2022 – Advised health system captive with respect to reinsurance claim pertaining to $25 million loss.
• 2022 – Counseled an internationally owned sporting goods company with respect to cyber coverage claim for federal intelligence agency investigation regarding theft of thousands of customer credit cards numbers.
• 2021-2024 – Pursued a business interruption and property loss insurance claim on behalf of retail bakery vandalized and looted in 2020 rioting following a civil rights protest.
• 2021-2024 – Litigated on behalf of nursing home client to overcome denial of coverage and efforts to rescind policy in light of operational disruptions resulting from COVID-19 governmental shutdown orders.
• 2021-2024 – Counseled manufacturer of consumer goods on ocean cargo insurance policy claim to obtain millions in coverage for cargo spoiled due to lengthy delays resulting from worldwide shipping crisis.
• 2020-2026 – Advocated for numerous policyholder clients with respect to COVID-19 business interruption losses under commercial property insurance policies, including for National Football League (NFL), Major League Soccer (MLS), state universities, health systems, restaurants, and hospitality entities, among others.
• 2020-2022 – Litigated long-tail environmental insurance coverage disputes, including federal lawsuit, on behalf of privately held fluid system products manufacturer with respect to historical insurance program with limits totaling in excess of $100 million.
• 2020 – Designed and implemented D&O strategy to assist client in efforts to collect $1 million-plus judgment against otherwise uncollectible entity.
• 2019-2021 – Litigated to settlement two related lawsuits in Ohio and Nebraska federal courts seeking to recover from various insurers (including a fidelity bond issuer) over $24 million in losses stemming from an alleged Ponzi scheme.
• 2019-2022 – Represented sports turf manufacturer and installer in insurance coverage litigation and settlement negotiations pertaining to cancelation of 2016 NFL Hall of Fame football game at Pro Football Hall of Fame in Canton, Ohio.
• 2019-2024 – Assisted publicly traded client with development and implementation of strategies to recover in excess of $20 million from insurance companies for nationwide environmental claims asserted by regulatory agencies and individual claimants.
• 2018-2026 – Helping chemical and solvents manufacturer protect approximately $4 million in captive insurer assets in connection with claim triggering multiple policies, including non-captive policy years.
• 2018-2026 – Advocating for large public university in efforts to secure insurance coverage for sexual misconduct allegations.
• 2018-2026 – Advising various high-net-worth family trustee clients on design and implementation of comprehensive D&O and professional liability/E&O insurance program.
• 2018 – Helped design insurance coverage program to protect against first-party and third-party risks associated with construction of entertainment facility on property owned by nationwide celebrity.
• 2017-2019 – Assisted with $15 million aviation insurance policy claim in connection with fatal aircraft incident.
• 2017 – Served as expert insurance coverage witness in the United States District Court for the Northern District of Ohio regarding rights and obligations under a captive professional liability insurance policy.
• 2016-2026 – Defended captive insurer of publicly traded power management company in litigation against claims by various traditional-market insurers seeking to shift historical asbestos liabilities in part onto captive, negotiating and now administering confidential reinsurance settlement involving claim for tens of millions of dollars.
• 2015-2017 – Aided NFL franchise with efforts to secure insurance coverage for class action under CGL, stop-gap employers liability and excess workers compensation policies.
• 2013-2026 – Assisting multiple performance materials manufacturers in management of international insurance programs, including review of coverage placements and asbestos and toxic tort long-tail claim cost-sharing arrangements under historical insurance policies.

Professional & Community

• American College of Coverage Counsel (ACCC), Member
• Greater Cleveland Food Bank, Longtime Supporter
• Assistant & Head Youth Soccer Coach (2021-2025)
• Leadership Council on Legal Diversity (LCLD), Law Student Mentor
• City of Cleveland and Junior Achievement, High School Student Mentor
• Cleveland Metropolitan Bar Association’s Insurance Law Section, Past Chair
• Numerous pro bono representations of underserved clients, including for Legal Aid Society of Cleveland (Community Commitment Honor Society Member), Cuyahoga County Common Pleas Court Diversion Program, and Quadriplegic Nursing Home Resident
• Cleveland Metropolitan Bar Association’s Committee on Mental Health and Wellness, Seminar Presenter and Past Chair
• Cleveland Bridge Builders Civic Leadership Program, Alumnus

Presentations & Publications

James speaks and writes regularly, including:

• Presented CLE program titled "Cyber Security and Data Breaches" at the Ohio Association of Civil Trial Attorneys (OACTA) 2025 Annual Meeting, discussing coverage issues and best practices relating to the ever-present threats involving cyber security and data breaches (November 14, 2025).
• Co-presented national CLE program on insurance coverage issues under the Trafficking Victims Protection Reauthorization Act, hosted by myLawCLE in July 2025
• Seventeen insurance coverage seminar presentations in past three years, including for clients, insurance brokers, trade associations, colleagues, Risk International, Ohio State Bar Association, Ohio Association of Civil Trial Attorneys, Cleveland Metropolitan Bar Association, Akron Bar Association, and Stark County Bar Association
• Co-authored and annually update LexisNexis Practice Note about parametric insurance, featured in September 2022 Practical Guidance publication
• Co-authored multiple articles included in the Cleveland Metropolitan Bar Association’s Insurance Law editions of its monthly "Bar Journal" periodical
• Hosted 2021 podcast episode with Director of Ohio Department of Insurance
• Frequently quoted by reporters in national articles on insurance coverage topics