K. James Sullivan

James’s primary focus is providing 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.

James is one of 23 lawyers certified as insurance law specialists by the Ohio State Bar Association. He is a member of the American College of Coverage Counsel (ACCC). He has served as an expert witness or arbitrator for insurance coverage matters multiple times.

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

Since 2020, James has been recognized for his work in Insurance Law in Ohio by Chambers USA, most recently ranked in 2024 in Band 1. Chambers USA researchers noted, "[James] is held in high esteem for his approach to complex recovery claims, which sees him handle a wide range of coverage disputes."

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 client’s goals and steers disputes to successful conclusions. He is an expert in his field. He is very practical, very clear-eyed, can really read the situation well, and has done a very good job. He understands the issues quickly, provides targeted, concise advice to 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 praised James for his "sophisticated and diplomatic approach to complex recovery claims, which sees him handle a wide range of coverage disputes. He does an excellent job of analyzing situations and getting good results."

James was named Best Lawyers^® 2018 Insurance Law "Lawyer of the Year" in Cleveland. He has been selected to The Best Lawyers in America list since 2017. Additionally, James has been selected for inclusion by Ohio Super Lawyers to the "Top 100 Attorneys in Ohio" list (2015-2025) and to the "Top 50 Attorneys in Cleveland" list (2015-2020, 2022-2025). In 2023, Business Today designated James as one of the "Top 10 Most Influential Insurance Lawyers in Ohio."

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

James was elected to Calfee's Management Committee in 2023.

Honors & Recognitions

• Chambers USA, Insurance, Band 1, Ohio (2020-2024)
• Ohio Association of Civil Trial Attorneys (OACTA) 2022 Respected Advocate Award
• Benchmark Litigation "Litigation Star" – U.S. (National) and Ohio: Insurance Litigation (2022-2025)
• The Best Lawyers in America^®, Commercial Litigation, Insurance Law, Litigation - Insurance (2017-2025)
• The Best Lawyers in America Insurance Law "Lawyer of the Year" in Cleveland (2018)
• Ohio Super Lawyers, Insurance Coverage (2014-2025)
  • Top 100 Attorneys in Ohio List (2015-2025)
  • Top 50 Attorneys in Cleveland List (2015-2020, 2022-2025)

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)
• Directors & officers (D&O)
• Side-A excess
• Difference in conditions (DIC)
• Professional services
• Errors & omissions (E&O)
• Tail & nose coverages
• Discontinued operations
• Fiduciary/employee benefits
• Trustee
• Employment practices (EPL)
• Stop-gap
• Captive
• Risk retention group (RRG)
• Representations and warranties (RWI)
• 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)
• Cyber (first-party + third-party)
• Business crime
• Employee theft
• Fidelity bond
• Sexual misconduct & molestation
• Surety
• Liquor
• Fine art
• Aviation
• 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:

• 2022-2024 – 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 pending in the U.S.
• 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.
• 2024 – Representing university in insurance coverage claims for NCAA concussion litigation.
• 2024 – Serving as an arbitrator for insurance coverage dispute between medical equipment company and its CGL insurers.
• 2023-2024 – Pursuing coverage from various lines of insurance for defense and indemnification of various third-party claims against Ohio window manufacturer collectively valued at over $50 million.
• 2023-2024 – Litigating federal and state insurance lawsuits on behalf of municipality for a $45 million wrongful imprisonment jury verdict.
• 2023 – Assisted Berkshire Hathaway portfolio entity with insurance coverage assessment pertaining to alleged third-party losses sustained in significant European facility accident.
• 2023-2024 – Litigating federal insurance lawsuit regarding failure of insurance company to provide coverage for nationwide product recall by publicly traded food manufacturer.
• 2023-2024 – Counseling 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.
• 2024 – Over the past decade through the present, 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.
• 2022-2024 – Negotiating multiple climate-related 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.
• 2022-2024 – Litigated $6 million-plus insurance broker malpractice claim on behalf of contract provider of physician and health care services.
• 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.
• 2022-2023 – Provided general insurance coverage counseling to rapid-growth multi-state residential apartment developer and manager, including with respect to renewals of various insurance policy lines.
• 2022 – Advised publicly traded advisory services client on late-notice dispute with high-level excess insurer regarding losses exceeding $5 million.
• 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 – Pursuing 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 – Counseling 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.
• 2020-2024 – Representing religious organization with respect to insurance coverage for multiple third-party lawsuits collectively seeking tens of millions of dollars, including matter that has evolved into federal insurance coverage lawsuit.
• 2020-2024 – 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.
• 2020-2021 – Represented private equity fund and platform company in connection with securing representations and warranties (RWI) and employment practices liability (EPL) insurance coverage for a class action involving international plaintiffs.
• 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.
• 2019-2021 – Advocated on behalf of hospital health system to recover D&O insurance proceeds to indemnify against multi-million settlements.
• 2019-2024 – Assisting publicly traded health care 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.
• 2019-2021 – Litigated and settled additional insured rights and contractual indemnification rights on behalf of publicly traded power company against national service provider pertaining to bodily injury claim seeking tens of millions of dollars.
• 2019-2020 – Advised seller client on preserving rights to insurance assets for pending third-party claim posing existential threat to M&A transaction acquisition target.
• 2019-2021 – Helped U.S. and international hotel chain with its efforts to secure coverage from various insurers to defend against anti-trust litigation.
• 2019-2020 – Counseled client on interplay among private equity fund’s financial services liability policy, portfolio company’s D&O policy and corporate indemnification agreements in connection with anticipated third-party claim.
• 2019 – Assisted client with development of strategy for pursuing over $20 million in cyber-attack losses from a combination of a cyber insurance policy and a third-party indemnitor.
• 2019 – Advised private jet client on potential formation of captive liability insurer.
• 2018-2024 – 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.
• 2018-2022 – Assisted manufacturing client in efforts to secure tens of millions of dollars in CGL and excess insurance for alleged catastrophic failure of client’s products affecting medical facility.
• 2018-2023 – Advocating for large public university in efforts to secure insurance coverage for sexual misconduct allegations.
• 2018-2021 – Helped publicly traded company secure and administer D&O and EPL coverage for SEC investigation.
• 2018-2024 – Advising high-net-worth family trustee client on design and implementation of comprehensive D&O and professional liability/E&O insurance program.
• 2018-2019 – Litigated alleged "late notice" denial of $2 million-plus coverage claim under CGL policy for home hardware component supplier.
• 2018 – Helped client negotiate with Ohio Department of Insurance regarding potential establishment of risk retention group (RRG) pursuant to Ohio’s RRG statutes.
• 2018 – Represented steel product manufacturer in efforts to secure legacy CGL coverage for asbestos litigation.
• 2018 – Advised client on CGL coverage protections for ongoing litigation spanning closing of stock purchase transaction.
• 2018-2024 – Frequently advise seller M&A clients on management of discontinued operations liability protections in connection with asset deals.
• 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.
• 2017-2024 – Helping company in medical insurance sector administer defense and indemnification claim under primary and excess E&O policies in municipal-law class action seeking an estimated $60‑70 million in alleged damages.
• 2017-2024 – Helping 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.
• 2017-2019 – Assisted with $15 million aviation insurance policy claim in connection with fatal aircraft incident.
• 2017-2018 – Represented lawn-care goods manufacturer in seven-figure dispute with property insurer over interpretation and application of deductible language in commercial property insurance policy.
• 2017-2018 – Advocated for manufacturing client in efforts to secure additional-insured status under third-party’s CGL program to fund defense and indemnification of death and severe bodily injury claims.
• 2017-2018 – Persuaded insurer to reverse denial of duty to defend toxic tort lawsuit by municipality seeking millions of dollars in damages.
• 2017-2018 – Represented insurance broker in connection with subrogation claim against insurer that wrongfully denied coverage under specialty liability policy.
• 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.
• 2017 – Helped design strategy for successfully sidestepping pollution exclusion raised by insurers for Ohio flooring manufacturer.
• 2016-2024 – Regularly advise numerous M&A clients on placement of RWI coverage.
• 2016-2022 – 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 confidential reinsurance settlement involving claim for tens of millions of dollars.
• 2016-2017 – Helped secure seven-figure recovery under D&O policy following arbitrated dispute involving disputes over loss allocation and identity of insureds.
• 2015-2024 – Assisting Fortune 500 company with design and administration of insurance coverage program for asbestos claim portfolio.
• 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.
• 2013-2024 – 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 (2021-2024)
• Law Student Mentor for Leadership Council on Legal Diversity (LCLD)
• High School Student Mentor for City of Cleveland and Junior Achievement
• Cleveland Metropolitan Bar Association’s Insurance Law Section, Past Chair
• Legal Aid Society of Cleveland, Community Commitment Honor Society Member (pro bono volunteer, 2024)
• Numerous Pro Bono representations of underserved clients, including for Legal Aid; Cuyahoga County Common Pleas Court Diversion Program; and Quadriplegic Nursing Home Resident
• Cleveland Metropolitan Bar Association’s Committee on Mental Health and Wellness, Annual Seminar Presenter and Past Chair
• Cleveland Bridge Builders Civic Leadership Program, Alumnus

Presentations & Publications

James speaks and writes regularly, including:

• Fifteen insurance coverage seminar presentations in past three years, including for clients, insurance brokers, trade associations, Risk International, Ohio State Bar Association, Cleveland Metropolitan Bar Association, Akron Bar Association, and Stark County Bar Association
• Co-authored 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 the Director of Ohio Department of Insurance
• Frequently quoted by reporters in national articles on insurance coverage topics