By Jameson Olive
Portrait by Gary James
It didn’t take long for Florida Panthers President and CEO Matthew Caldwell to realize his father wasn’t afraid to go to great, sometimes crazy lengths to ensure his son’s happiness.
“When I was 5 or 6 years old and we’d go to Yankees games, it always felt like he was working something,” says Caldwell, who grew up with a sister, Doreen, and two brothers, Billy and Scott, in New York City. “He was always getting us through an inaccessible gate or somehow getting me closer to the field. He always had a way of gaining unbelievable access without money or power. He did everything through charisma and bulldogging. He was relentless in making sure his kids got the best.”
A 35-year veteran of the NYPD, William “Wild Bill” Caldwell speaks with a thick New York accent and is the type of man who could easily strike up a conversation with anyone in the five boroughs—and, according to his family, he usually does. On the outside he comes across as a burly and intimidating figure, but after only a few minutes you’ll notice the lovable, charismatic man hidden beneath that hardened, blue-collar exterior.
And although he’s always lived a life worthy of his “Wild Bill” nickname, it wasn’t until a summer visit to the U.S. Military Academy at West Point—where Caldwell enrolled in 1998—that his now-infamous moniker came to fruition and took on a life of its own.
“Even the Army couldn’t stop him,” Caldwell says, laughing. “He’d never stay in the designated areas on campus and would always bring things like 6-foot hero sandwiches for the other cadets and me. It got to the point where one of my friends would yell out, ‘It’s Wild Bill again!’ whenever he’d visit. It was the perfect nickname. We don’t even call him Dad anymore.”
After graduating from West Point in 2002, Caldwell served as a military officer in the U.S. Army until 2007 in Germany with deployments to Iraq and Kosovo. He reached the rank of captain—a nickname he now holds within the Panthers organization—while serving in the military.
Following his time in the armed forces, Caldwell went on to earn a doctorate in law and an MBA from Northwestern University. To his dad’s delight, he moved back to the Big Apple shortly after graduation, taking a job in financial services at Goldman Sachs, where he would become a vice president in its investment management division.
It was while serving in the military, however, that Caldwell truly learned the lengths Wild Bill would go to for his family, as his father’s never-say-no attitude led to an impromptu trip around the world just to wish his son a happy 23rd birthday. From New York to Zurich to Kosovo, Wild Bill traveled under the guise of an officer in the police training program, talking his way past checkpoints and cruising through the war zone, eventually reaching Camp McGrath just in time to surprise a dumbfounded Caldwell on his big day.
“He pulled out a grainy black-and-white printout from Yahoo with a map of Europe and driving directions from Zurich to Kosovo,” Caldwell says. “He pointed to Europe with his finger and said, ‘I figured if I got here that I could figure out a way to get across the Mediterranean to Kosovo.’ At the time, Kosovo wasn’t even a recognized country, so you couldn’t find it on a normal map. I’m still amazed.”
After Caldwell spent years telling stories like these from the battlegrounds of the Middle East to the trading floor of Wall Street, he finally decided to put pen to paper to write Wild Bill: The Legend of America’s Craziest Father, a collection of short stories showcasing the adventures of his family’s larger-than-life patriarch.
“Whether I was working on Wall Street or sitting around a campfire in Iraq, I’d be telling funny Wild Bill stories,” Caldwell says. “Every time I told these stories, whether it was to a group of soldiers or a table of financial executives, there was always complete and utter laughter. It’s a family dynamic everyone can understand. It’s love and it’s passion, but it can be crazy. I learned that my father is someone nearly everyone can relate to.”
A self-published author, Caldwell has already sold about 700 paperback and digital copies of his book through Amazon Marketplace, with all of the profits going toward the college funds for Wild Bill’s five grandchildren.
“I’m not an author. I’m not trying to sell books. I just wanted to get the best stories down on paper,” Caldwell says. “The book was something I initially just wanted to give to my dad. It wasn’t a trip to Kosovo, but it made for a good present on his 70th birthday.”
In 2014, Caldwell began what has since proven to be one of the most successful chapters of his own amazing life story, plucked from bullpen of the trading floor by billionaire Wall Street investor Vincent Viola to oversee the development of one of his latest and most unusual financial endeavors—a hockey team he had recently purchased in South Florida.
“I really got connected to Vinnie during a business dinner, and I told a Wild Bill story,” says Caldwell, who served as chief operating officer of Sunrise Sports & Entertainment for two years before ascending to his current role. “I told him the story about Wild Bill visiting Kosovo. When I’m telling that story, people can’t believe that he actually he did all of those things. But when I started telling Vinnie the story, he cut me off and said, ‘Don’t even tell me your father showed up in a warzone.’ He’s the only person that ever guessed that. His dad was also pretty wild, so he could see a fellow crazy New Yorker doing that.”
In his role with the Panthers, Caldwell can often be found doing his best Wild Bill impersonation, as the 36-year-old executive works tirelessly to inspire his staff to grow and sell the sport of hockey in South Florida. Like his father, he’s learned that you can’t have success without taking risks, and nothing is more important than the relationships you make with people.
“In life and in business, relationships are everything,” Caldwell says. “From Yankee Stadium to Kosovo, I watched my father live that sentiment.”
Originally appeared in the Spring 2017 Issue.