As national counsel for several insurance companies, Cliff previously litigated and arbitrated high stakes coverage cases throughout the United States on issues ranging from environmental claims to asbestos, sexual abuse and molestation, hearing loss, "repetitive stress," pharmaceuticals, implants, and products incorporated into building. After years of litigating, Cliff has for the past 20 years specialized in negotiating settlements serving both as an advocate and as a neutral mediator, including building bridges and orchestrating amicable global resolutions of high profile, high stakes disputes.

Cliff's work in the dispute resolution area extends beyond the insurance field. Cliff had been named to mediate cases for the U.S. D.C. Circuit Court of Appeals, the U.S. District Court for the District of Columbia, and the Superior Court of the District of Columbia. Cliff has also arbitrated cases for the District of Columbia Bar's Attorney's Fee Arbitration Board. For example, the U.S. District Court for the District of Columbia appointed Cliff to try to mediate to resolution a 20 year long dispute over whether thousands of hours of taped conversations recorded by former President Richard Nixon would be released to the public. Notwithstanding that prior 20 years of contentious litigation, Cliff built effective working relationships with the counsel involved and achieved a mutually acceptable settlement among representatives of the Nixon family, Public Citizen, the National Archives, and a University of Wisconsin Professor of History.

Cliff's pro bono experience included the Clark v. Library of Congress case which he tried for the A.C.L.U. on the issue of First Amendment limitations on federal investigations of lawful political activities by government employees and won in the D.C. Circuit Court of Appeals and then negotiated a practical resolutions to implement the Court’s rulings.

From 1978 to 1979, Cliff served as a law clerk to the Honorable Ben Duniway on the U.S. Court of Appeals for the Ninth Circuit in San Francisco. He has been named one of the top lawyers in the insurance field by Chambers USA. Cliff has also been recognized by multiple editions of The Best Lawyers in America, the International Who's Who of Business Lawyers, and Super Lawyers in the area of insurance law.