PROFILE: Tom Cross

March 13, 2021
By Marcy Shortuse

BY T MICHELE WALKER – When Dos Equis beer created their “Most Interesting Man in the World” advertising campaign, the ads featured a bearded, debonair gentleman with voiceovers that were both humorous and outrageous. Boca Grande has its own version of that icon in Tom Cross, who gives him a run for his money. 

Born and raised in Jasper, Alabama, Tom was a Cub Scout, a Boy Scout, an Eagle Scout, and played a lot of sports. He recalls his upbringing in, as he called it, a “solidly middle-class home.”

“My father managed a brick plant, and Mom was a stay-at-home mom, later going to work for the Department of Human Services,” he said. 

One thing you might notice when you meet Tom is the lack of an Alabama accent. 

“It depends who’s on the other side,” laughed Tom. “A southerner says, ‘Are you a Yankee?’ But back home in Connecticut, they think I have a big southern drawl.”

At an early age Tom was faced with a monumental decision. 

“In Alabama, before you’re able to talk and by the time you are 5, you have to declare yourself as an Alabama fan or an Auburn fan. Both of my parents were Alabama grads, so it was an easy decision, and a big part of our fall social life from ages 10 to 16. Football is in the blood in Alabama.”

Not surprisingly, Tom’s first date with his lovely wife, Kitty, was at a football game. 

“Kitty and I met at Vanderbilt. Oddly enough, our first date was to an Alabama/Vanderbilt game. Vanderbilt won, which made it unusual. Alabama came into the game as a 22-point favorite, but Vanderbilt won in the fourth quarter. I was trying to root for Vanderbilt, but I just couldn’t do it. About halfway through the fourth quarter, I started twitching. Kitty asked me ‘Who are you for?’ and I said, ‘I am trying to be for Vanderbilt, but I just can’t.’ That night that was the highlight for those at Vanderbilt, but it was not a happy night for me.”

Vanderbilt went on to beat Alabama, and Tom and Kitty eventually married. 

After attending the University of Alabama and Vanderbilt University, Tom worked as a systems analyst, then assistant director for fiscal affairs for the Alabama Commission on Higher Education in Montgomery. Tom joined Price Waterhouse in Birmingham in 1976, relocated to Dallas, and was eventually transferred to New York City as a partner. There he served served as global chairman of Price Waterhouse’s Consumer and Industrial Products Industry practice.

“It’s all an adventure,” admitted Tom.

Since the family loved living in Dallas, the move was met with some hesitancy. However, the beauty of New Canaan, Connecticut grew on the Cross family. 

“We still have a house there all these years later. We love the town, love the people so it all worked out. We now split the year between New Canaan and Boca Grande. It’s a tough life, but somebody’s got to do it.”

It was while sitting in his Manhattan office at Price Waterhouse that Tom was hit by the travel bug.

“I’m sitting in my office in midtown Manhattan, February of 2004, and I get a random email from one of my partners saying, ‘I just booked a round trip to Anchorage, Alaska to spend a week hiking in the Denali backcountry. Anybody interested in joining me?’ Just 30 minutes later, seven of us were doing electronic high fives to celebrate our upcoming trip.”

While at the time the trip just seemed like a “one-off” adventure, it lit a fuse. From that moment, Tom Cross the Trail Boss was born. 

Kitty and Tom’s daughters are his constant inspiration. “The girls are fantastic and responsible for my career as a hiker,” Tom said. “They both went to undergrad school at Princeton, where incoming freshmen are given a week to do an urban or outdoor adventure. Princeton puts you with 12 other freshmen for the week, so when you attend school in the fall, you know somebody.”

Both daughters chose to do an outdoor trip, which turned out to be an Appalachian Trail hike.

“They both loved the experience so much that my youngest daughter volunteered and signed up to be a leader for these trips,” Tom said. “She took outdoor first aid courses and learned outdoor skills to be a trained guide, so it was fascinating when I was bitten by the bug that my younger daughter quizzed me about the terrain, or phone service, or what would you do if this kind of animal showed up, or if one of your hikers twisted an ankle. An inspiration and a twist where the kid is instructing the dad.”

Father-daughter adventures are a regular thing for the Cross family.

 “My older daughter who doesn’t have little kids anymore has been able to recently joined me on a father-daughter trip to Patagonia. Two years ago, the summer before the pandemic, six of us and our daughters did a combined hiking and flyfishing trip to Jackson Hole, Wyoming.”

When asked about his favorite trip, Tom hesitated. “It’s like asking which kid so you like best. They’re all special.”

After thinking for a moment, Tom added, “ As far as eye candy, I’d say the Himalayas for the stunning majesty. Hands down, it is the most amazing terrain I have ever seen. From 18,000 feet, we had a line of sight to four of the highest peaks in the world. It was visually stunning.”

He continued.

“The happiest trip would have to be Kiliminjaro in Tanzania, which is a volcano on a flat plain. The vegetation and trees are different, not necessarily majestic but when you get up to the top, there are permanent glaciers that are up there and they are stunning.”

In all of the majesty and beauty, what touched Tom most were the people. 

“The people in Tanzania were amazing, especially in the central part of the country. The country is largely Christian. I might argue that they have an equal or a better value system than we do. They are remarkable, loving, joyful people that care about family. Whatever job they have, they are dedicated to it.”

Tom said as there were 20 people on the trip, which was a big group for a trip like that. 

“Two-thirds will usually make it to the summit, but we all made it,” he said. “We had 60 porters, three cooks and eight guides. The team was like an army, but that’s the way they do it. We wanted to say thank you, so they had us arranged in a circle with all of our gear in the middle. It just so happened that this was my 65th birthday ,and the cook had whipped up an impromptu cake which they presented, along with Kilimanjaro beer. Everybody was in an amazing mood. Then I gave out the tips. When the first porter came through and I gave him a 100 U.S. “Benjamin,” the guy almost went to his knees. It was the first time he had ever seen or held that much money. When the second guy came through, he started crying. I asked the main guy what was going on, and he said, ‘You just paid for two years of school for that guy’s kids. You can’t imagine what kind of impact you’re having on their lives.’ Their gratitude and philosophy of living were powerful, and an amazing experience. I can’t wait to go back.”

Even with the shutdown, Tom stays in shape in a fun way. “With all the hikes that I do, they’re walks. We don’t require ropes or gear. I literally train by walking golf courses and carrying my golf bag. From the time I get out of a car until I get back, I walk seven miles, more or less.”

Carrying 25-30 pounds is terrific training, and on the days Tom doesn’t golf he takes long walks on the island.

“My steps per day, at my best, were 20,000, on average. I have gotten less rigorous lately, and now average 16,000 to18,000 a day. One fun on-island adventure is to climb the Gasparilla Lighthouse. The views are astounding and it’s fun to do.”

Tom’s next adventure is this September, where he will be traveling to the Julian Alps in Slovenia. “I’ve never been before. We finish in Croatia above the Aegean Sea along the Dalmatian coast.”

While slowing down is not in Tom’s vocabulary, he does admit that he is starting to run out of ideas for new adventures, but won’t allow that to stop him. Exploration is his passion and one that he loves to share in his second career.

While the pandemic has slowed down world travel, Tom has exciting offerings for the Boca Grande community. Be sure to stay tuned, as next season Tom will take to the stage and will present “A Backpacker’s Guide to the Wilderness.”  

Wherever Tom travels, you can be assured that just like “The Most Interesting Man in the World,” he might be quick to say, “Remember my friend … wherever you are is where you’re at.”