Following his term at CLIPI, Dillman clerked for two years for Judge Laughlin E. Waters of the U.S. District Court for the Central District of California.

Dillman then served as partner at Augustini, Wheeler & Dillman, a boutique litigation and trial practice firm in Los Angeles. In 1998, Dillman joined, as partner, Hennigan, Mercer & Bennett, a prominent boutique law firm renowned for its complex litigation, especially in bankruptcy and securities cases.

After 2011, Dillman played a leading role as partner at McKool Smith, specializing in complex commercial litigation and trial practice, primarily in the areas of finance, securities, energy, real estate, trade secrets, partnership, and healthcare fraud.

Over the years, Dillman was consistently recognized as one of the nation’s leading litigators by numerous legal publications. In 2018, the Los Angeles County Bar Association awarded him the Jim Robbie Award, presented annually to the trial attorney who best exemplifies the qualities of both professionalism and civility. 

During his 40+ years of practice, Dillman served as lead counsel for among others, religious and financial institutions and technology companies, and regularly litigated high-profile actions against many of the world’s largest public companies. His notable representations include securing more than $400 million in settlements from Bank of America and others on behalf of lenders in connection with claims arising from the financial collapse of the Fontainebleau Resort and Casino project in Las Vegas. He also represented the Archdiocese of Los Angeles in a wide variety of commercial matters, including a dispute that made international news and involved the sale of the former convent Villa San Giuseppe to pop star Katy Perry.

Dillman played a critical role at CLIPI as a trustee for about a dozen years, serving as President during the period in which CLIPI officially closed its doors in 2007.

Dillman passed away in December 2025.