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Private Company with annual revenues up to $500 million- Patrick O’Leary

Vice President and General Counsel- The Bar Plan Mutual Insurance Company, St. Louis

Even while Patrick O’Leary was in the midst of a good career in finance and accounting, he always knew in the back of his mind he wanted to go to law school.

Finally, when he was 36, he decided it was time to start.

“I felt like if I didn’t do it before I was 40, it was likely I would never do it… and I was going to regret that,” he said.

Going back to school later in life did have some challenges – technology had changed and O’Leary had to get back into the academic mindset, but it also had advantages – he wasn’t interested in the partying side of school and could better focus.

O’Leary graduated at age 39 and began working for then-Missouri Attorney General Jay Nixon’s office.

After three years there, O’Leary got a call from Karen McCarthy, now president and CEO of The Bar Plan, where O’Leary had clerked over the summers in law school, offering him a job as general counsel.

“I was already familiar with them from my clerkship, I knew they were a well-run company and a company with a good purpose,” O’Leary said.

Another key reason he accepted the job was the opportunity to work under McCarthy, who had previously been his supervisor.

“I respected her a lot, she is very bright and focused and articulate,” he said. “I knew it would be a good position for me.”

McCarthy speaks highly of O’Leary as well, saying he is a “lawyer’s lawyer” and “every executive’s dream.”

“He is intelligent, thoughtful, even tempered, and measured in everything he does,” she said. “But most importantly, he is persistent in making sure his concerns are heard, and understood, before moving on to the next issue.”

McCarty said O’Leary provides excellent counsel when discussing issues or analyzing situations.

“He doesn’t tell you what you want to hear, he tells you what you need to hear,” she said. “I have the utmost respect for and faith in Pat and am so happy he is receiving this recognition he so rightly deserves.”

Moving to The Bar Plan was a bit of a change of pace from the attorney general’s office, where O’Leary worked in litigation and served as general counsel of credit unions. At The Bar Plan, he became the chief legal officer of a highly regulated company and his focus was on making sure the company stayed in compliance with all applicable laws and regulations.

When asked what he liked best about his job, O’Leary cited the management team he works with and the fact that he’s been given so much responsibility in addition to his role as general counsel, which he said makes for an interesting challenge.

Since becoming a lawyer, O’Leary said he’s had many proud career moments, including passing the bar and getting his law license, arguing cases in front of the state’s appellate court while working for the attorney general’s office, helping found Lawyers for Equality, the LGBTQ bar association O’Leary is a past president of, and chairing The Missouri Bar’s insurance committee.

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