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Jack Siegel repped his biggest client—Mom—against CVS

Published in 2022 Texas Rising Stars magazine

Ask Jack Siegel why he became an attorney, and he responds with characteristic directness. “I’m a five-foot-eight-inch Jewish kid. I was never going to be an athlete,” he says. “This is what I do instead.”

To be more exact, what the 39-year-old employment litigator does is win. “I just don’t go into cases thinking I’m going to lose,” he says. “The way I see law is, it’s a fight. Am I going to get my ass kicked? Or am I going to outfight them?”

That’s what he did in the 2019 class action in which he represented more than 15,000 plaintiffs, including his mother Susan, against the CVS prescription benefit subsidiary Caremark. 

Siegel had grown up on the north side of San Antonio in a working-class family. He was 13 when his dad lost his job, and his mom began working for CVS. “She’s probably the most important person to me in the world,” he says. “I always hated the company because they treated her like crap despite her working for them for 18 years.”

In 2014, when Susan was terminated from her position as a customer service representative at a CVS call center, her son initially wanted to pursue an age discrimination case. “She had a younger boss, and that boss thought she wasn’t catching up quickly enough,” Siegel says.

He admits that, at the beginning of his career, he wouldn’t have known what to do with a case like the one against Caremark. But, as he began to delve into the details of his mother’s situation, he realized there might be more at stake. Prior to starting her shift at the call center, Susan and her colleagues had to become “call ready,” which meant logging into specific computer programs and doing other tasks that might take up to 15 minutes to complete. Callers usually engaged in similar tasks at the end of their shifts as well. 

“It just hit me that they might not be paying them correctly before or after their shifts,” says Siegel. “And it turns out I was right.”

When Siegel checked if similar cases had been brought against CVS, he discovered that a lawsuit had been filed against subsidiary Caremark two years earlier in Missouri. That lawsuit was in limbo, however, because attorneys were having trouble bringing in employees from all 15 of CVS’s call centers. Leveraging his mother’s situation to sway other customer service reps, Siegel was able to bring representatives into the case from around the country. He and the other attorneys working on the lawsuit drafted a conditional certification motion, which was granted nationwide in August 2016. Suddenly, the case went from having $2 million at stake to approximately $15 million.

But there were hurdles. At one point, it looked as if previously signed arbitration agreements with other employees might derail the collective action, though Siegel wrote a successful brief and the court denied Caremark’s motion to compel. Then, Siegel and his co-counsel discovered that Caremark had begun erasing call records, which ultimately strengthened the plaintiffs’ case.

Throughout, Siegel wasn’t sure if the suit would settle or head to trial—“I really cut my teeth throughout litigation of that case,” he says. In the end, a $15.25 million settlement was reached in 2019.

These days, Siegel is focused on what’s in front of him. With his colleague Travis Hedgpeth, a close friend from law school, Siegel is currently working on pending lawsuits against Magellan Health, Presbyterian Health Services and United Health in New Mexico—which has among the strongest wage protections in the U.S. More than $80 million is at stake. 

Regardless of how those cases end, however, nothing will top the Caremark suit. “I might make more money off a future case,” Siegel says, “but doing that one for my mom? It’ll be the highlight of my career.”

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