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James represents closely held and publicly traded business clients on a variety of matters, including the following:

  • Providing insurance coverage services to policyholders
  • Litigating contract, business tort, and equitable claims
  • Advising on contract interpretation
  • Facilitating alternative dispute resolution efforts

He has litigated in many Ohio appeals and trial courts, as well as numerous federal trial and appeals courts.

Additionally, James counsels clients on designing and administering promotional sweepstakes.

James is one of 24 Ohio lawyers certified as an insurance law specialist by the Ohio State Bar Association. He has served as an expert witness on insurance coverage issues.

Chambers USA 2020 ranked James as a Band 1 "Leading Lawyer" in Insurance in Ohio. Chambers noted that James "is held in high esteem as one of the best policyholder lawyers in Ohio. He is also praised for his sophisticated and diplomatic approach to complex recovery claims, which sees him handle a wide range of coverage disputes. One source reports, 'He does an excellent job in analyzing situations and getting a good result. He is smart, well respected and capable in the courtroom.'"

He 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. James has been recognized by Ohio Super Lawyers as one of the top 100 attorneys in Ohio and one of the top 50 attorneys in Cleveland from 2015-2020.

James joined Calfee in 2001 and was elected Partner effective January 1, 2010. He serves as chair of Calfee’s Associates Committee and is a member of its Diversity & Inclusion Committee. He also serves as a formal and informal mentor to other Calfee attorneys.

Honors & Recognitions

  • Chambers USA, Insurance, Band 1 (2020)
  • The Best Lawyers in America©, Commercial Litigation, Insurance Law, Litigation - Insurance (2017-2021)
  • The Best Lawyers in America© Insurance Law "Lawyer of the Year" in Cleveland (2018)
  • Ohio Super Lawyers (2014-2020)
    • Ohio Super Lawyers, Top 100 Lawyers in Ohio list (2015-2020)
    • Ohio Super Lawyers, Top 50 Lawyers in Cleveland list (2015-2020)


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

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

Certified “Insurance Law Specialist” by the Ohio State Bar Association



Insurance Policyholder Recovery and Counseling Services

James has been litigating on behalf of and counseling insurance policyholders on coverage matters since 2004. More than 90% of James’s practice is 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
  • Discontinued operations
  • 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)
  • Fiduciary
  • Employment practices (EPL)
  • Stop-gap
  • Representations and warranties (RWI)
  • Employed lawyers
  • Public entity
  • Educators legal liability (ELL)
  • Crime
  • Fidelity bond
  • Sexual misconduct
  • Surety
  • Liquor
  • Aviation

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

  • 2020 – Designing and implementing D&O strategy to assist client in efforts to collect $1 million-plus judgment against otherwise uncollectible entity.
  • 2019-2020 – Litigating 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.
  • 2019-2020 – Representing sports turf manufacturer and installer in insurance coverage litigation pertaining to cancelation of 2016 NFL Hall of Fame football game at Pro Football Hall of Fame in Canton, Ohio.
  • 2019-2020 – Advising seller client on preserving rights to insurance assets for pending third-party claim posing existential threat to M&A transaction acquisition target.
  • 2019-2020 – Assisting 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.
  • 2019-2020 – Helping U.S. and international hotel chain with its efforts to secure coverage from various insurers to defend against anti-trust litigation.
  • 2019-2020 – Counseling 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.
  • 2018-2020 – 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.
  • 2018-2020 – Assisting 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.
  • 2018-2020 – Advocating for university in efforts to secure insurance coverage for sexual misconduct allegations.
  • 2018-2020 – Advising client in health services sector on multi-million-dollar claims under multiple lines of insurance.
  • 2018-2020 – Helping publicly-traded company secure and administer D&O and EPL coverage for SEC investigation.
  • 2018-2020 – 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.
  • 2018-2019 – Assisted with design and implementation of insurance coverage strategy for talc litigation for home-improvement goods manufacturer.
  • 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.
  • 2018-2019 – Advised multiple seller M&A clients on management of discontinued operations liability protections in connection with asset deals.
  • 2018 – Represented Chinese manufacturer client against insurance subrogation claim.
  • 2018 – Advised pump manufacturer on structure of insurance coverage program, including public-company D&O, EPL, fiduciary, crime and excess policies.
  • 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.
  • 2017-2020 – 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.
  • 2017-2020 – 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 – Advised commercial real estate company on key property insurance coverage issues in connection with losses sustained during Hurricane Maria.
  • 2017 – Assisted specialty chemicals manufacturer secure millions of dollars in CGL defense and indemnity coverage in connection with construction manufacturing defect claims.
  • 2017 – Helped design strategy for successfully sidestepping pollution exclusion raised by insurers for Ohio flooring manufacturer.
  • 2016-2020 – Regularly advised numerous M&A clients on placement of RWI coverage.
  • 2016-2020 – Guiding health sector client through dispute with third party seeking to waive client’s rights with respect to approximately $125 million in limits under medical professional liability insurance.
  • 2016-2020 – Defending 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.
  • 2016-2017 – Helped secure seven-figure recovery under D&O policy following arbitrated dispute involving disputes over loss allocation and identity of insureds.
  • 2015-2020 – Assisting Fortune 500 company with design and administration of insurance coverage program for asbestos claim portfolio.
  • 2015-2017 – Aided professional sports franchise with efforts to secure insurance coverage for class action under CGL, stop-gap employers liability and excess workers compensation policies.
  • 2015 – Advised multiple Calfee clients regarding rights with respect to D&O insurance in connection with lawsuits and claims brought by third parties.
  • 2015 – Advised multiple Calfee transactional clients on insurance coverage issues in connection with U.S.-based and internationally-based stock purchase agreements and asset purchase agreements, including with respect to insurance anti-assignment provisions and successor access to historical insurance policy rights.
  • 2015 – Assisted nationwide insurance brokerage and risk-management firm with development of endorsement language to present to the insurance marketplace.
  • 2015 – Assisted disability-management company’s efforts to secure insurance coverage for defense costs and indemnity coverage in connection with defamation lawsuit.
  • 2014-2015 – Assisted material handling equipment company with securing total defense and indemnity coverage for its first-ever asbestos claim.
  • 2014-2015 – Assisted aviation services company with securing defense costs for employment practices punitive class-style claims.
  • 2014-2015 – Assisted nationwide financial services company with obtaining settlement from insurer when insurer argued policy at issue had lapsed.
  • 2014-2020 – Assisting performance materials manufacturer in coverage in place agreement negotiations with multiple insurers regarding asbestos and other toxic tort long-tail claims.
  • 2014-2015 – Secured multi-million-dollar settlement against Fortune 500 insurer in connection with breach of contract claims.
  • 2014 – Performed comprehensive insurance coverage program review for D&O, EPL, fiduciary liability, and crime coverage for service provider of Cloud-based communications and applications.
  • 2014 – Assisted lifestyle shopping center secure property insurance for losses resulting from rupture of frozen pipes that affected over 15 of its tenants.
  • 2011-2015 – Sought in excess of $5 million in EPL coverage for a designer and manufacturer of corrugated packaging.
  • 2013-2020 – Assisting commercial construction goods manufacturer in its efforts to secure coverage for CERCLA Superfund liabilities under historical policies.
  • 2013-2020 – Assisting performance materials manufacturer in management of international insurance program, including review of coverage placements and asbestos claim coverage under historical policies.
  • 2011-2020 – Managing asbestos and benzene product liability insurance coverage claim program on behalf of former automotive product manufacturer.
  • 2011-2013 – Helped secure favorable settlement in lawsuit seeking over $15 million in coverage under a property policy for a Michigan client that suffered catastrophic property and business interruption losses at its petroleum-based product storage facility.

Banking Commercial and Retail Litigation

Since 2001, James has handled more than 125 matters for Ohio banks, including many for three of Ohio’s four largest banks. James has a wide variety of experience in banking litigation, including trials, hearings, appellate arguments, depositions and dispositive motions.

Representative sample of recent services James has provided to bank clients:

  • 2019-2020 – Protecting bank’s interests in connection with alleged mismanagement of investment account funds and errors and omissions in placement of life insurance policy.
  • 2018-2019 – Defended bank against allegations of wrongful foreclosure, resulting in favorable settlement of claim.
  • 2018-2019 – Litigated arbitration matter involving allegations of Telephone Consumer Protection Act (TCPA) violations by banking client.
  • 2018 – Advised bank on proper management of funds subject to restraining orders issued by federal court judge in connection with criminal investigation, including interfacing with U.S. Attorney’s office as instructed by judge.
  • 2017-2018 – Guided bank client through matter involving misuse of IOLTA account funds by banking customer.
  • 2016-2017 – Helped bank fend off consumer claim pre-suit that was precluded by account holder terms and conditions.
  • 2016-2017 – Litigated claim against bank alleging mismanagement of confidential information despite legal process mandating disclosures.
  • 2015 – Assisted bank fiduciary in resolution of commercial real estate dispute.
  • 2014 – Assisted bank in addressing claims for breach of fiduciary duty by a customer.
  • 2014 – Assisted bank with fraud investigation regarding a franchisee banking customer.
  • 2013 – Advised bank on nuances of various Uniform Commercial Code commercial paper provisions in connection with bank’s development of policies and litigation strategies.

General Business Litigation

Representative sample of general litigation services James has provided to Calfee clients:

  • 2019-2020 – Representing private equity fund and its portfolio company with claims against the seller of a portfolio company and a software supplier regarding the supplier’s breach of contract and the supplier’s related allegations of fraud by the seller.
  • 2019 – Advocated on behalf of surgical technology supplier in earn-out dispute.
  • 2019 – Advised remote monitoring software company on protecting highly privileged information and limiting the scope of its production to adverse directors.
  • 2018-2019 – Prosecuted claim on behalf of manufacturing client against supplier of defective goods that jeopardized client’s relationship with key customer.
  • 2018 – Advised client on successor liability theories and methods for protecting against related claims.
  • 2017-2018 – Defended landscaping materials company against defective goods allegations.
  • 2017 – Advised client with respect to indemnification rights and obligations in connection with contract with worldwide rubber goods manufacturer.
  • 2016 – Represented area business in breach of contract claim in connection with Republican National Convention in Cleveland, Ohio.
  • 2015-2020 – Litigated numerous claims involving alleged breaches of representations and warranties in stock purchase agreements and asset purchase agreements on behalf of various private equity clients.
  • 2015-2018 – Defended manufacturer of retail and commercial paints and coatings against class-style claims alleging breach of contract and violation of Ohio’s business opportunity plan statute.
  • 2015-2017 – Defended recycling industry client in hotly contested dispute over contracted value of scrap metal, resulting in confidential mediated settlement.
  • 2014 – Defended manufacturer client against breach of contract claim by Sony Pictures Home Entertainment Inc., resulting in favorable settlement.
  • 2014-2015 – Defended real estate developer against third-party beneficiary claims.
  • 2014-2015 – Obtained favorable settlements in multiple software developer and administrator lawsuits.
  • 2013–2015 – Litigated on behalf of golf course management company against municipality to recover hundreds of thousands of dollars in capital improvements for which municipality wrongfully withheld payment.
  • 2013 – Negotiated settlement of federal lawsuit brought by Sunoco, Inc. against client in accordance with client’s strategic objectives for minimizing total cost exposure associated with potential CERCLA Superfund liabilities.

Sweepstakes and Games of Skill Promotions and Consumer Laws Counseling

James has counseled corporate clients on approximately 50 sweepstakes and games of skill promotions since the early 2000s, including the legality of promotions; the structuring and implementation of promotions to comply with federal, state, and local statutes, regulations and common law; the use of social networking media in promotions; and protection against unintended liability resulting from promotions.

Representative sample of sweepstakes and games of skill counseling provided to clients by James:

  • 2019 – Promotion involving series of sweepstakes to celebrate retail client’s 40th business anniversary, culminating in grand prize of new vehicle lease.
  • 2019 – Baseball-themed sweepstakes promotion for international manufacturer and supplier of professional cleaning supplies.
  • 2018 – Debit card giveaway promotion for energy broker.
  • 2018 – Religious organization liquor raffle promotion.
  • 2016-2019 – Multiple trade-show promotions.
  • 2017 – Bluetooth-enabled device prize promotion.
  • 2017 – Sweepstakes awarding client home furnishings products as prizes.
  • 2015-2016 – E-billing enrollment programs for multiple clients.
  • 2016 – Customized shoe design skill contest for flooring manufacturer.
  • 2015 – Points program grocery store cart fill-up promotion for health-care company employees.
  • 2014 – Photography contest featuring client goods.
  • 2014 – Guidelines for promotional sweepstakes in the United States for a Canadian client for use in U.S. consumer and commercial transactions, with supplemental U.S. publicity and privacy guide.
  • 2013 – Advised multiple clients on issues relating to establishment and administration of customer loyalty programs.
  • 2012 – Design and administration of $1 million cash promotional sweepstakes giveaway for Ohio energy supplier.

Clients' Work

Professional & Community

Professional & Community

  • Cleveland Metropolitan Bar Association’s Insurance Law Section, Past Chair
  • Legal Aid, Numerous Pro Bono Representations of Under-Served Clients 
  • Cleveland Metropolitan Bar Association’s Committee on Mental Health and Wellness, Past Chair
  • 2008 Cleveland Bridge Builders Civic Leadership Program, Alumnus
  • City of Cleveland, High School Student Mentor

Presentations & Publications

Presentations & Publications

James speaks and writes regularly, including the following:

  • "2019 Ethics and Professional Conduct CLE Program" Calfee, Halter & Griswold LLP, Cleveland, OH (2019)
  • "Annual National Insurance Litigation Seminar," American Bar Association (2014, 2015, 2018)
  • Frequent speaker at seminars sponsored by the Ohio State Bar Association, Cleveland Metropolitan Bar Association, and Akron Bar Association. Most recently presented:
    • "Beware the Trip Wires: How to Protect and Maximize Insurance Coverage Assets," Association of Corporate Counsel (October 2019)
    • "Beware the Trip Wires: How to Protect and Maximize Insurance Coverage Assets," Ohio State Bar Association (January 2020)
  • Co-authored articles included in the Cleveland Metropolitan Bar Association’s 2019 and 2020 Insurance Law editions of its monthly “Bar Journal” periodical
  • Co-authored the featured cover article for the American Bar Association’s Winter 2015 issue of "The Brief"
  • Quoted in an article titled, "COVID-19 Pendulum to Swing" for Business Insurance's October 2020 issue

News & Events



Licensed In

  • Ohio

Court Admissions

  • U.S. District Court for the Northern District of Ohio
  • U.S. District Court for the Northern District of Georgia
  • U.S. District Court for the Southern District of Ohio
  • U.S. District Court for the Eastern District of Michigan
  • U.S. District Court for the Eastern District of Pennsylvania
  • U.S. District Court for the Eastern District of Missouri
  • U.S. District Court for the Eastern District of Wisconsin
  • U.S. District Court for the Middle District of Florida
  • U.S. District Court for the Western District of Pennsylvania
  • U.S. District Court for the District of Nebraska
  • U.S. Court of Appeals for the Sixth Circuit
  • U.S. Court of Appeals for the Eighth Circuit
  • U.S. Court of Appeals for the Eleventh Circuit
  • U.S. Supreme Court

"James Sullivan is held in high esteem as one of the best policyholder lawyers in Ohio. He is also praised for his sophisticated and diplomatic approach to complex recovery claims, which sees him handle a wide range of coverage disputes."
Chambers USA 2020

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