Texas Jury Awards $91 Million in Family Battle Over Major Waste Company

Verdict finds CEO of one of the nation’s largest independent waste operators breached fiduciary duties through self-dealing transactions, according to court findings

AUSTIN, Texas — A Texas jury has awarded more than $91 million in damages in a closely watched family business dispute involving the chief executive of one of the nation’s largest independent waste and recycling companies.

A Travis County jury found that Bob Gregory, CEO of Texas Disposal Systems, breached fiduciary duties to the company through transactions that benefited entities he controlled, according to court findings described in case materials.

The verdict stems from a lawsuit brought by Jennifer Gregory and her father, Jimmy Gregory, Bob Gregory’s brother and former business partner, in a dispute over the governance and finances of the Austin-based company the family built over decades.

The plaintiffs alleged Bob Gregory engaged in self-dealing by steering company business through separately owned entities, including a leasing company that purchased vehicles and leased them back to Texas Disposal Systems. The lawsuit also accused him of dramatically increasing his compensation without approval, from $300,000 in 2019 to roughly $2 million by 2022.

Bob Gregory’s legal response was not included in the materials reviewed, and it was not immediately clear whether he plans to appeal.

Family dispute threatens leadership at major waste operator

The verdict could create uncertainty around leadership at Texas Disposal Systems, which has grown into a major independent player in waste hauling, landfill operations and construction debris recycling.

Jennifer Gregory said the jury’s findings could allow a judge to appoint a receiver to oversee the business, arguing the verdict showed governance failures at the company.

“The verdict puts the leadership of one of the country’s largest independent waste operators in play,” she said in a statement included in the case materials.

The lawsuit traces the family conflict back decades, describing an arrangement between the Gregory brothers that allegedly gave them shared control over the company. Plaintiffs argued Bob Gregory later undermined that structure through unilateral compensation decisions and affiliated-party transactions.

Self-dealing allegations drove the case

A major component of the damages involved Okapi Leasing, a company plaintiffs said Bob Gregory used to structure transactions with Texas Disposal Systems for his personal benefit.

The case centered on fiduciary duty claims — a legal theory that corporate leaders must act in the best interests of the companies they manage rather than their own financial interests.

Texas Disposal Systems has long maintained a significant presence in Central Texas and is active in recycling and waste diversion operations, including construction and demolition material recovery.

Bob Gregory was recognized in 2024 with an ethics award from an Austin nonprofit organization, underscoring the sharp contrast between the company’s public image and the allegations presented in court.

Final judgment still pending

The jury verdict does not automatically end the case. A judge must still enter final judgment, and post-trial motions or appeals could alter the outcome.

Still, the size of the award marks a significant development in a dispute over control of a major privately held company — and one that could reshape leadership at a prominent Texas waste operator.