From West Point to war to Wall Street to the NHL to the NBA: Matthew Caldwell’s road to Minnesota

The photo caused Scott Caldwell’s phone to light up with wisecracks about his little brother. The snide comments included the word “idiot,” or some variation of it.

A viral image showed the Florida Panthers arena at opening faceoff at the second home game of the 2014-15 NHL season. The crowd was so small voices would have echoed in the building.

Business acquaintances of Caldwell’s sent texts wondering why on Earth would his kid brother, Matthew, give up a thriving career at Goldman Sachs in New York City to oversee business operations of a downtrodden professional hockey team in south Florida.

They let him know what they thought of that career move.

Big bro shot back a guarantee: His brother would win a Stanley Cup.

“He just figures everything out,” Scott said. “Anything that you think is impossible, he will get done.”

The receipts show that Matthew won two Stanley Cups and helped build the Panthers into a model sports organization.

Next up for the 45-year-old: Securing a new arena for the Timberwolves and Lynx as their new chief executive officer.

“It was an opportunity I couldn’t pass up,” he said over a beer in downtown Minneapolis.

Caldwell’s background reads like a movie script.

West Point graduate. Army combat veteran. Earned law degree and MBA simultaneously. Career on Wall Street. Successful professional sports executive. Married to a Brazilian lawyer.

“I dreamed of doing something great in life,” he said.

The Sept. 11 terrorist attacks took place the fall of his senior year of 2001-02. President George W. Bush delivered the commencement speech at West Point the following June.

“I knew I would be going to war,” Caldwell said.

He graduated as a second lieutenant commissioned officer assigned to the Army’s 1st Infantry Division, known as “Big Red One.” He was sent to Kosovo on a peacekeeping operation.

Caldwell’s 23rd birthday was near. His dad, Bill, had been planning to wish him happy birthday in person. Caldwell reminded him that Kosovo was a combat zone with no commercial flights.

“At the time,” he said, “it was literally a piece of land that the Serbians and Albanians were fighting over.”

Caldwell was answering radio calls in an operations tent when a superior entered and asked to see Lt. Caldwell outside.

Said Caldwell: “I go outside, and I hear, ‘You think I wouldn’t see my son on his 23rd birthday?’”

Standing there was Wild Bill in an NYPD hat and shorts that he always wore to play slots in Atlantic City.

How he pulled it off sounds stranger than fiction.

His dad went to the airport with a map of Europe that he printed off MapQuest. He circled Kosovo in yellow highlighter.

The plane landed at an Army air strip. Bill confessed his scheme to the pilot and asked for help getting home in a few days.

Said Bill: “He says, ‘Listen, I’m not supposed to be here. I finagled my way on here to go visit my son on his birthday.”

They worked out a deal once the incredulous pilot stopped laughing.

Using a military phone at the air strip, Bill called around to different bases asking if they had a Lt. Matt Caldwell. He identified himself as a captain with the NYPD and said he was part of an official government program and wanted to see his son.

“He’s telling me this story and I’m like, ‘Oh my God,’ ” Matt Caldwell said. “So now I’ve got to go see my colonel. I’m soiling my pants.”

The colonel’s reply, according to Caldwell: “Son, I’ve been in the Army 30 years. I never seen anything like this. Your father is not in any police program, but God bless him for getting here.”

Word of Wild Bill’s ruse reached Caldwell’s closest friends on the base.

“Having a family member show up in a combat zone is the equivalent of a martian landing next to me and coming over to say hi,” said Chris Boggiano, who served alongside Caldwell as an officer. “It’s not part of your reality.”

Bill was not permitted to sleep on the base. He joined a patrol unit that evening. They stopped at a ramshackle home and through an interpreter, Bill offered the owner 50 euros to sleep there. The man invited him in.

“There is an Albanian in Kosovo who is telling this story right now about a crazy American who slept at his house,” Matt Caldwell said, shaking his head in wonderment.

He served as a tank platoon leader with 40 soldiers under his command. His battalion was responsible for patrolling six Iraqi towns with an objective of bringing peace and stability to the region.

“I learned a lot about leadership,” he said. “I would never ask my soldiers to do something that I wouldn’t do. I had to be the most physically fit. I had to be willing to kick in the door myself.”

He was barely out of college, tasked with leading dozens of soldiers in combat.

“Not that I liked war, but I liked being able to serve my country in a time of need,” he said. “It doesn’t matter if you’re white, Black, Hispanic. If someone is going to defend you and pick up a rifle, it equalizes everything.”

He considered staying in the military beyond his five-year obligation. An itch to try something else landed him in Northwestern University’s accelerated three-year program that combines a law degree and Master of Business Administration in one swoop.

He passed the bar exam and had an offer from a prominent NYC law firm but instead accepted a job at investment bank Goldman Sachs, where he worked his way up to vice president. One of the firm’s clients was billionaire businessman Vincent Viola, a fellow West Point grad.

Viola took a liking to Caldwell and hired him to help manage family investments. Viola purchased the NHL’s Panthers in 2013 and convinced Caldwell to switch career paths. In 2016, at age 36, Caldwell became the youngest CEO in the four men’s professional sports leagues.

“When you’re trying to turn something around,” Caldwell said, “you’ve got to try something [different].”

The organization experienced a seismic turnaround. From bottom of NHL standings to back-to-back Stanley Cup champions. From sluggish ticket sales to sellouts and record TV viewership. The Sports Business Journal recognized their success on and off the ice by naming the Panthers the 2025 “Sports Team of the Year.”

Caldwell’s transition to a new career also brought personal fulfillment that sprouted from a case of serendipity.

The woman was visiting from Brazil for a month and headed to a bakery in the West Village. Caldwell told her he lived close by and offered to make sure she found the place.

“Even if I didn’t live in that area, I would have told her I was going,” he said with a laugh, adding, “I wanted to marry her on the spot.”

Caldwell asked for her number. They met for drinks a few days later, but that was extent of their interaction. She lived in Brazil so logistics wouldn’t work, she said.

Fast forward five years. Caldwell was living in Florida. A friend got married in Brazil. Caldwell served as best man and stayed a few extra days for vacation. He posted a picture of Brazil on Facebook.

He had no communication with the woman from the subway in those five years. Somehow, Facebook’s algorithms brought that photo into the woman’s feed.

They exchanged messages, the vibe clicked. He invited her to visit him in Miami. She accepted.

“And we fell in love,” he said.

He married Fernanda in 2018, and they have three children, ages 6, 4 and 1.

A call from new Wolves owners Marc Lore and Alex Rodriguez stirred a new adventure for the family outside the cocoon they enjoyed in Florida.

Caldwell had reached the pinnacle in the NHL and worked for an owner who treated like him a son. He found the NBA’s global reach appealing, along with the challenge of getting a new arena built. Lore and Rodriguez showed their commitment by offering a 10-year contract.

He describes his leadership style as “authentic.” Boggiano, a friend since 2003, observed Caldwell’s leadership under the most intense circumstances: in combat.

“If you would ask all of his peers who was the best lieutenant in the battalion,” Boggiano said, “I think it would be pretty close to universal that everybody would agree that it’s Matt. He is such a good leader that he can even give people bad news, and they still love him.”