Missouri Lawyers Awards 2025: David Cosgrove

Managing Member, Cosgrove Law
St. Louis

With two attorneys and four paralegals, David Cosgrove isn’t running the largest outfit in town but the digital age is becoming the great equalizer.  

“Definitely as a smaller firm, you need, to the extent possible, to leverage technology to compete on a national level,” said Cosgrove, a former Commissioner of Securities for the State of Missouri who founded his firm 17 years ago.

That conviction has fueled the firm’s work with AI, including the creation of a program that is able to employ a large language model that listens to recordings of salespeople in the financial products industry and highlights potential compliance issues.

“We evaluate the quality of the feedback it provides and either edit or add to that feedback,” he said. “It saves us an enormous amount of time and so far, it has been very successful in terms of issue-spotting for us.”

This allows the small firm to serve clients that might otherwise look to a larger organization.

“It is a massive volume of information to analyze trying to make sure that 50-100 salespeople are selling their product in a compliant fashion,” said the 59-year-old Notre Dame graduate. “There is only so much data we can consume so the use of AI is definitely going to help us punch above our weight in terms of the amount of data we can consume and therefore the amount of appropriate legal advice we can provide.”

Cosgrove believes that the AI revolution in law is still in its infancy.

“Artificial intelligence has to be utilized with great care, particularly around issues relative to attorney-client privilege,” said Cosgrove who spent much of the 1990s working in the state attorney general’s office litigating civil and criminal cases.  

Cosgrove, a winner of the Missouri Bar’s Lon O. Hocker Award, served as chief legal counsel to former Gov. Holden before his stint as securities commissioner. He also worked in the Massachusetts Attorney General’s office in the Consumer Protection Division and as a Special Assistant United States Attorney for the District of Massachusetts.