Please Advise

Jim Martin

Rich Gross discusses his legal career and his current work with local veterans 

As a young man, Rich Gross knew deep down that he wanted to be a lawyer. He also knew that there was no money set aside for his education. “I had two criteria,” Rich explains. “It had to be free, and it had to be different.” He met both of these stipulations when he discovered a brochure for the U.S. Military Academy at West Point and was subsequently accepted.

Upon leaving West Point, he served as an Infantry lieutenant in the 82nd Airborne, a post he kept for five years. After successfully applying to the Army’s Funded Legal Education Program, Rich was finally able to realize his childhood dream, earning his Juris Doctor degree in 1993 from the University of Virginia Law School and entering the Army’s Judge Advocate General’s Corps (JAG).

Some years into his JAG career, Rich was given an unusual request. “I was asked to interview for a job,” Rich says. “I didn’t know of any jobs that you interviewed for in the Army. They usually told you to do a job.” That job was to serve as legal counsel for the elite Delta Force, a group tasked with some of the most important and dangerous missions carried out by the Armed Forces.

Close friends tried to dissuade him from taking the post. They worried that he would never be promoted. Rich had a completely different take. “I thought, what a chance,” Rich says. “What an opportunity to do something fun and cool.” After beating out three others interviewing for the position, Rich dove head first into his new job. “I wasn’t afraid to ask questions and play the new guy,” he says.

Little did he know that the nature of his work, and even more, the world, would change drastically shortly afterwards. “Three months after I got there, 9/11,” Rich recalls. “So, you can imagine, all of a sudden there’s a big change in our missions and what we were doing and how busy we got. From that time forward, that put me on a different path.”

This path led him to several deployments in both Iraq and Afghanistan, putting his mettle to the test both personally and professionally. “It’s very intense. It’s very focused,” Rich explains. “You have, essentially, one mission. All day long you’re focused on the mission of the unit you support.” The time away from his family was trying, but he is quick to count his blessings. “You’re always in a little bit of danger, frankly, but it’s not like those young Marines and young soldiers out on patrol, walking through a village, not knowing if they’re going to step on an IED or get shot from a window. Those are the ones that really have a tough time when they deploy.”

Throughout this time, Rich continued to ascend in rank, serving as legal counsel for many key players in the military. For a little over a year, he served as the chief legal advisor for General Stan McChrystal, the senior commander of all U.S. and NATO forces in Afghanistan. He then went on to serve as chief legal advisor for General Jim Mattis at U.S. Central Command (CENTCOM), where he oversaw a team of lawyers responsible for legal issues pertaining to all military operations in the Middle East. Lastly, he spent his final four years in the Army as the chief legal counsel of General Marty Dempsey, Chairman of the Joint Chiefs of Staff before retiring with the rank of brigadier general after over 30 years of service in 2016.

When asked about the types of issues he dealt with in these high positions, Rich was quick to point out just how broad his purview truly was. “You’ve got to be, as we say, a mile wide and an inch deep,” he explains. Much like corporate lawyers, he oversaw things like personnel issues. “You have investigations, whether someone gets hurt, someone loses equipment, or somebody harasses someone.” Unlike corporate law, Rich was tasked with advising commanders with decisions that carry all the gravity attached to active combat. Decisions had to be made quickly. “If you’re in the middle of a targeting operation, and the question is, do the rules of engagement and the laws of armed conflict, the laws of war, allow you to strike this target or this person? You can’t say, ‘Hey, sir. Let me go call an expert and read a few books and get back to you.’ You have to answer that question.”

In all of the decisions that Rich helped inform, a number of them have left an indelible mark; there were times that stick out in his memory where he felt especially proud that he was able to steer those he advised in the most positive, progressive direction. “Long before Abu Ghraib, long before detention became the sensitive issue it did… In 2002, I was asked for some legal advice on how we were conducting some detention operations. I gave some strong advice that we needed to move in a different direction. And we did.”

His courageous stance held water, and a long memo that he penned concerning the matter was entered into a Senate Armed Services Committee report on detention operations as an example of doing the right thing.

It’s an excellent example of Rich’s philosophy on legal counsel. “I considered myself legal counsel. Two words.” Rich goes on to explain, “Here’s the legal advice, but also here’s the counsel. The legal says what you can do. The counsel is what you should do.”

With such an impressive career, one might expect a domineering personality giving up very little to anyone in his periphery. In fact, Rich is one of the most affable people that you’re likely to meet, and he possesses a humility not seen in many people whose careers have soared to such heights. Although very proud of his military career, he is reluctant to bring up his rank. He is much more excited to talk about the work he does now, hoping that his enthusiasm will encourage others to get involved with the non-profits he is involved with currently.

Rich (left) on stage with fellow Bunker Labs city leader Derren Burrell Lt. Col. (Ret.) (center) and guest speaker Randy Boyd (right) at a Bunker Brews event at Boyd’s Jig & Reel in January of this year.

One such organization is Bunker Labs, a group that assists veterans aspiring to become entrepreneurs. Rich became aware of the non-profit while working for a small, veteran-owned law firm in the Washington D.C. area after that firm became a sponsor of the local Bunker Labs chapter. Offering legal advice at monthly meet ups, he developed an admiration for the work being done to assist his fellow service members. And upon moving back to East Tennessee for a job at Janus Global Operations, he was quickly recruited to help develop Knoxville’s newly formed chapter by friend and Bunker Labs city leader, Derren Burrell. The group now holds monthly meet ups to help veterans develop viable, thriving businesses using three basic tenets: equip people, inspire people, and connect people.

In addition to Bunker Labs, Rich serves on the boards of three non-profit organizations, The Independence Fund, Military Community Youth Ministries, and the Spookstock Foundation, all of which are dedicated to serving veterans and military families. Most recently, he joined the George W. Bush Stand-To Veteran Leadership Program, an initiative dedicated to helping people who work with our country’s veterans operate more effectively and efficiently.

While his career has taken him all over the world, Rich is genuinely excited to return to Knoxville. “It’s such a vibrant city, and you really appreciate it when you’ve left and get to come back,” he says beaming. And Knoxville is lucky to have him.

For more about Bunker Labs, visit   

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