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Jury returns $116 million verdict against TDS CEO Bob Gregory in Family Business Dispute

In May 2026, a jury in Austin returned a verdict finding actual and exemplary damages totaling over $116 million against Texas Disposal Systems CEO Bob Gregory. His brother, Jimmy Gregory, brought the lawsuit, both individually (for Bob Gregory’s breach of a contract at issue in the litigation) as well as derivatively on behalf of the TDS Companies (for Bob Gregory’s breach of fiduciary duties owed to the TDS Companies).

The jury found that Bob Gregory breached his fiduciary duties to TDS and its affiliates that he and Jimmy Gregory have owned and operated together for decades. The jury found actual damages totaling over $91 million that Bob Gregory caused to the TDS Companies as a result of his breaches of fiduciary duties to the companies. After finding Bob Gregory acted with “a specific intent to cause substantial injury to the TDS Companies,” the jury returned an additional verdict for exemplary damages against him in excess of $23 million. The jury also found that Bob Gregory breached a contract with Jimmy Gregory related to, among other things, TDS shareholder distributions and salaries, with damages to Jimmy Gregory totaling $1.4 million. Altogether, the actual and exemplary damages that the jury found against Bob Gregory are in excess of $116 million.

The fiduciary breach verdict centers on claims that Bob Gregory used entities he wholly owns — Okapi Leasing, LLC, Okapi Environmental Services, LLC, and Txalloy/Acme Iron and Metal — to the financial detriment of the TDS Companies. The $91 million portion of the verdict was secured on behalf of the TDS Companies, although the trial court judge has the authority to award some or all of those damages directly to Jimmy Gregory in a final judgment. In addition, based on the jury’s findings that Bob Gregory abused his authority over the TDS Companies with intent to harm the companies, and, by doing so, created a serious risk of harm to certain TDS Companies and that, under his control the property of those TDS Companies is being “misapplied or wasted,” the trial court judge now has authority to enter a final judgment appointing a receiver to ensure that the TDS Companies are run with appropriate oversights and managerial controls.

Congrats to SDM trial team Casey Dobson, Sara Clark, Abe Kuczaj and Kennon Wooten!

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