By David Laprad

After 20 years of raiding drug houses, eavesdropping on hackers and keeping tabs on terrorists, FBI Special Agent Jason Lawless decided to do something less stressful – become an attorney.

Upon retiring from the Federal Bureau of Investigation at 50, Lawless landed at Gearhiser, Peters, Elliott & Cannon in Chattanooga, where he intends to develop a cybersecurity practice.

Lawless is no stranger to the practice of law or Chattanooga. An Alabama native whose widowed mother moved to the Scenic City after she remarried, he graduated from McCallie School, earned an international studies degree at Georgia Tech and then became a proud alumnus of the University of Tennessee College of Law.

After working as a prosecutor in the district attorney’s office in Nashville for four years, he finally received the call on which he’d been eagerly waiting – an invitation from the FBI to serve his country.

Although Lawless expressed a desire to return to Chattanooga after completing his training at the FBI Academy, commonly referred to as “Quantico,” the agency sent him to Washington, D.C., to earn his stripes.

Here, Lawless discusses the dangers and excitement of working for the FBI and setting those things aside to practice at a small and serene Chattanooga law firm:

Asking why you pursued a job with the FBI seems like a good place to start.

“It’s also an easy place to start. I was raised on TV shows and movies about the FBI, and it seemed like it would be a cool adventure. At the same time, I thought it would satisfy my desire to serve.”

Was serving as fun as you’d imagined it would be?

“When you’re a young agent, you think working for the FBI is going to be super fun and cool, like ‘Miami Vice.’ But that’s not what that world looks like. The first time you raid a drug house, it’s terrifying. And the way some people are living is sad.

“Also, things that are exciting the first time you do them – such as mobile surveillance or chasing a suspect – become routine. I remember thinking, ‘Great, we’re going to be sitting in a car for eight hours today.’ I’d have to remind myself that not everyone gets to do what I do.”

You started in counterintelligence. What was that like for a former prosecutor accustomed to putting drug dealers and murderers behind bars?

“Culture shock. But it was also interesting because I was able to see some of the bigger picture and learn why the United States cares about certain things and why it’s important to protect this country.

“One of the things I liked about being a prosecutor was the freedom to pursue justice, whether it involved dropping a hammer on a sex criminal, or showing mercy to someone who was a victim of their circumstances and could be rehabilitated. I had cases where, against certain people’s wishes, I showed mercy, and I had cases where I had to withhold mercy to protect society.

“When I became an agent for the FBI, I was still pursuing justice, but in a different way.”

Your work eventually led you to various stints with cybersecurity. Fast forward to when you were a squad supervisor in D.C. What was your most memorable case?

“We had a case in which we extradited someone from Europe who was laundering money for a hacking group. We indicted the hackers, which went against my nature as a counterintelligence guy because you don’t indict people in counterintelligence, you spy on them. But we knew who the hackers were and they were committing crimes that were costing Americans and Europeans hundreds of millions of dollars – despite not being very good at what they were doing.

“One thing they did caused the stock market to hiccup, which was impressive for such an untalented bunch. If they ever make the mistake of traveling to a country with an extradition treaty with the U.S., they’ll be arrested and brought here to enjoy our justice system.”

After a stretch in St. Louis, where you supervised a joint terrorism task force, you veered into senior executive territory, which distanced you even further from the hands-on part of missions. Did you still feel like you were serving justice?

“In a way. When I returned to headquarters, I created a business management division that oversaw our technology infrastructure. The FBI has 56 major offices in the U.S. and computers for 38,000 employees. So, when Microsoft releases a new version of Windows, the agency has to make sure those computers aren’t too old for the upgrade.

“The FBI essentially wanted someone minding the money, which was out of my comfort zone. I’m a special agent and a former prosecutor, not an MBA. But we did save the agency millions of dollars because of the way we approached certain things. I also enjoyed learning about the business end of the stick.”

Your CV with the FBI is far more extensive than we have space to discuss. However, what was your most challenging career move?

“My son and daughter loved North Virginia, so when the FBI transferred me to St. Louis, I promised we could return if the agency ever promoted me again. I later put in for four senior executive positions, three of which would have been in either Northern Virginia or D.C. One was in Maryland, however, and that’s the one I got. I’d made a promise, though, so we moved back to North Virginia and I made the 56-mile commute to Fort Meade every day in D.C. traffic.”

What was the lesson there?

“Be careful what you promise in life.”

What led to your decision to retire from the FBI at 50?

“My ambition outran my happiness. Stopping is hard; there’s always another promotion to chase. But at a certain point, I realized I was doing what I was doing just to receive the next rank or title and I was no longer having fun.”

Why become a lawyer at a firm? Why not consult from your home office?

“I wanted to use my experience in a way that would be satisfying. I considered working in the IT industry, but my heart wasn’t in it. I’m from here, and my wife loves it here, and I wanted to be a part of this community. Many IT jobs are remote, but contracting with a company out of Northern Virginia and talking with them over Zoom every day wouldn’t allow me to be a part of this community.”

Your wife, Gigi Lawless, is an estate planning and administration attorney at Gearhiser. Did that play a role in you joining that firm?

“Absolutely. She loves her work and the people here, so when the firm asked me if wanted to practice law again, I said yes. However, I want to focus on things I know; I don’t want to tackle something new. So I’ll be concentrating on cybersecurity and IT legal issues and probably doing some criminal defense work.”

What kind of case might you take?

“Companies are dealing with a deluge of regulatory issues in cybersecurity and data privacy right now. My experience will allow me to walk clients through those scenarios and make sure they know the laws, which are constantly changing.

“I’ll essentially be an adviser. If a large bank is in the midst of a ransomware situation, for example, its leadership might have questions. Do they need to call the FBI? Should they tell a regulator? I’ll use my experience in that world to identify their options and guide them through that situation.”

Considering all you experienced while working for the FBI, does anything about living and working in Chattanooga rattle you?

“Being in a car my teenage son is driving. It’s terrifying. Kids don’t realize how dangerous that is because they’re young, but when you’re 50, you think only about the dangers.”

How do you relax after a ride with your son?

“I’ve taken up golfing. I’m terrible at it but I need something to keep me active and get me outside, especially as I cross 50. I’m not a hunter and I don’t fish, so golf it is.”