
Joe Montgomery went to his first football practice when he was in the second grade even though you couldn’t play until the third.
“You have to assume that I was committed to the process early,” smiles Montgomery as he looks back on his youth in Lynchburg, Virginia, long before he was an All-American, pursued by Division I colleges and meeting people who would change his course, and his life.
Montgomery sat down with WYDaily to talk about his recent honor as the latest recipient of the prestigious Gerald R. Ford Legends Award. The award, named after the 38th president of the United States, is presented to a former collegiate or professional center who, in addition to a standout football career, has also made significant contributions to the football or business communities or through philanthropic endeavors.
Montgomery is Managing Director of Investments at The Optimal Service Group of Wells Fargo Advisors, a career he began after fifteen years of organized football. Today, he is a member of the Barron’s Financial Advisor Hall of Fame, and consistently listed in the publication’s Top 100 Financial Advisors, a ranking more likely seen on Wall Street than in Williamsburg.
The way Montgomery sees it, it was a combination of football, mainly while playing at the College of William and Mary, that was the conduit to accomplishments.
“Playing football at William & Mary is also conditioning you to be in an environment where you are something other than the biggest and strongest; it has more to do with the mental things that you pick up from football,” he explained.
“William and Mary is very important to me. I’ve been very fortunate.”
Montgomery was a stand-out player at Brookville High in Lynchburg. He was an all-district nose guard and center and was recruited heavily by the coaches at nearby Virginia Tech.
“I would have gone to Tech, which was a clear choice. They recruited me hard, I lived in Lynchburg and was taken to a lot of games.”
During his official recruitment visit, Virginia Tech’s head coach Jerry Claiborne told Montgomery how much they wanted him to play for the program, that he could have a significant career and likely become an All-American. Claiborne finished his pitch by telling Montgomery how the team would be traveling to Houston to play on Astroturf, a big deal at the time.
Then William & Mary football coach Lou Holtz was also recruiting Montgomery, and he told the high school star that Montgomery was the only center they were going to draft.
Montgomery laughs, “If you think about it, he probably didn’t have any money to recruit another [center] anyway, but I didn’t know that.”

Virginia Tech’s efforts to convince Montgomery to choose the Hokies didn’t stop after his visit. Montgomery recalls one of those occasions when the doorbell rang, and the school’s chief recruiter was standing on the stoop. Montgomery went to get his father.
“I thought you told him you weren’t ready to make a decision,” said Montgomery’s father.
“I did,” replied Montgomery.
“This is where you realize your parents are a whole lot smarter than you give them credit for,” laughed Montgomery, as recounts what happened next.
“Thanks for coming,” began his father. “Joe did tell you he’s not ready to make a decision, right? Well, he’ll let you know when he is ready,” after which he politely showed the recruiter to the door.
Watching the Super Bowl and eating chocolate cake with Lou Holtz
Shortly after that, Joe Montgomery made his decision. He would go to William & Mary.
“I was seventeen and started thinking “huh, a college decision based on Astroturf. And it’s not even our Astroturf.”
Montgomery called Virginia Tech coach Claiborne to tell him of his decision. Claiborne was gracious and congratulated the Lynchburg senior, assuring him he would do very well. Then he called Coach Holtz and recounted what happened next.
“I called Coach Holtz on Saturday morning. He was delighted and said, “I’ll be right up.” I explained to him that my parents would be at a wedding, Holtz said. “Well they need to be there, so I’ll come up tomorrow.” “Coach,” I said, “Tomorrow is the Super Bowl.” “Oh, I’ll watch it at your house,” Holtz replied.
“So, there he is, we’re in the den with little TV trays, and he’s eating my mother’s German chocolate cake, and we’re watching the Chiefs and the Vikings in the Super Bowl. When I look back on it, it seems surreal.”
At William & Mary, Montgomery was a two-time first-team All-Southern Conference and Big Five selection at center, culminating his collegiate career as co-captain for the Tribe in 1973.
“William and Mary played a major part in my career success, and I owe it so much. Playing for Coach Holtz was a transformative experience. He was meticulous; he knew everything about you, he made you believe you were better and could do better.”
On January 13th, 2018, as Joe Montgomery prepared to accept the Gerald R. Ford Legends Award in Lincoln, Nebraska, a video screen came to life at the front of the hall, and the now 81-year-old coach Lou Holtz began speaking from his home, personally congratulating Joe Montgomery and his accomplishments.
https://youtu.be/ckBqIMbUxK4
From football to financial advice
Montgomery had already signed a contract with the Philadelphia Eagles in February of his senior year. He was there for nine weeks and six preseason games.
“I ran 100 plays over the hottest summer in Philadelphia in 100 years, every single play in the scrimmage,” he recalls.” But shortly after that, the Eagles cut Montgomery to make room for a kick returner. His professional career included another tryout with the Jets and finally a move to the WFL’s Charlotte Hornets before the new league collapsed.
Back in Lynchburg, not sure if his football quest had come to an end, Montgomery heard from a college friend.
“I used to work the door at this dive bar in Lynchburg,” he says about his return to home.
“I was still thinking, I’m going back to the NFL.”
Meanwhile, a William & Mary alumnus named Larry Phillips, the manager of Wheat First Securities in Lynchburg, told Montgomery’s friend that Phillips wanted to meet with Joe about going to work for Phillips.
“I go down to see the guy, and he was determined to hire me because of the William & Mary connection,” says Montgomery. When asked if Montgomery has thought about a career in financial investments, he laughs.
“You know I didn’t have a clue in my head because I thought I wanted to be a dentist.”
Phillips did a bit of a Lou Holtz recruiting of his own to convince Montgomery, first to take a job with him in Lynchburg, and later to move to Williamsburg to open a new office.
Montgomery returned to Williamsburg in 1979, where he has remained a staple within the college and city communities ever since.
Montgomery is a founding member of the Williamsburg Community Foundation and the Williamsburg Community Health Foundation. He also served as a director with the Williamsburg Community Hospital. Currently, he serves on the boards of the Virginia Retirement System, the Virginia Capital Foundation, and the Colonial Williamsburg Foundation.
“Being on the board of Colonial Williamsburg Foundation is very important to me,” Montgomery said. “I really enjoy that. It’s important that we see to it that Colonial Williamsburg continues to succeed and thrive.”
The definition of retirement
When Joe Montgomery was told that he would be the latest recipient of The Gerald R. Ford Legends Award, it carried with it the unintentional gift of causing him to reflect, knowing it is not the award itself that is meaningful, but the things one has done in the process.
“From the William & Mary Athletic Hall of Fame to the Barron’s Hall of Fame, the bridge is the great experience at William & Mary, and carrying all those tools we learned from coaches like Lou Holtz and the outstanding teammates we had as we continued on in our lives.”
In Montgomery’s view of his life path and the future, his philosophy is simple.
“Life works out the way it’s supposed to. That’s kind of the journey.”
“I love what I do. If you define retirement as being able to do what you like to do, am I not already retired?”