A torn rotator cuff in the minor leagues destroyed David Highmark’s dreams of making it to the big leagues, but baseball’s loss was sports management’s gain. Highmark is now president of FineMark Sports Management, a division of FineMark Bank and Trust in Fort Myers.

The management arm represents nearly 300 athletes and manages about $500 million of their money. It recently expanded by opening an office in Jupiter, Florida.

Highmark created the sports management division in 2012 when he started FineMark Bank in Scottsdale, Arizona. Highmark moved from Naples to Scottsdale in 1997 to run Northern Trust. He was looking for a change in 2011 when he called his friend Joe Catti, who’d founded FineMark in Fort Myers in 2006. They’d both worked at Northern Trust in Miami and in Southwest Florida.

Catti thought Highmark wanted to return to Southwest Florida, and offered him the job of creating a Naples office. But Highmark said he wanted to stay in Scottsdale.

“So, I said to him, ‘All right, if you want to stay in Scottsdale and you’ll agree to run the bank, then we’ll open there—and when do you want to start?’” Catti recalls. “That’s how it really began.”

In his final years at National Trust, Highmark headed up the professional sports division, so when he moved to FineMark, some athletes followed. He started with a couple of Major League Baseball players he knew through coaching their sons in Little League.

“A year later we went from two to 10, and then another year later, we had 20 to 25 and before you know it, today—23 years later—we’ve got over 300 athletes,” Highmark says.

The majority of FineMark’s clients are golfers and baseball players, with a few hockey and football players mixed in. The sports management arm also has caddies and some sports executives.

“It’s a difficult business to build because it’s all based on trust,” Highmark says. “Too many professional athletes have been scammed during their careers and end up with nothing. So, they can tend to be very wary and suspicious of those that do what we do.”

Former Major League pitcher Bronson Arroyo said he became a fan of Highmark during a lunch in 2003. Highmark asked Arroyo how he budgeted and paid his bills. Arroyo replied that he stockpiles his money and pays his bills monthly. Highmark said he couldn’t help him; to keep doing what he was doing and when he made more money Highmark could help.

“I knew—in a world of ‘car salesmen’ in that industry—when he told me that, I knew he was a man,” Arroyo says.

FineMark does more than invest an athlete’s money. “We simplify their lives. We’re a family office for these athletes,” Highmark says.

FineMark pays their bills, files their taxes, lends them money for homes, boats and other items, does estate and long-term planning.

LPGA golfer Anna Nordqvist has been a client since she turned pro in 2009.

“Dave has probably been the single most important person in my career,” says Nordqvist, who went to Arizona State University and is from Sweden. “They’ve been there helping me buy my first car, buy my first condo, my second condo, buy my first house,” she says.

Being a full-service bank gives FineMark an advantage, Highmark said. Sometimes he will get a call on a Sunday afternoon from a client who needs a loan to buy a home they’re looking at. Highmark knows whether the client can afford that home and, if so, can write a pre-qualification letter and send it to the real estate agent in 30 minutes.

The Monday morning after a golfing client makes money in a tournament is another example. FineMark calculates what the caddy is owed, adds a tip and wires the money to the caddy’s bank account—and sometimes, the caddy’s account is with FineMark, too.

“It’s a unique model because it’s under the umbrella of a bank, and we can move very, very quickly on things,” Highmark says.

Catti’s comparison: FineMark Sports Management moves like a jet ski and not an ocean liner.

Highmark isn’t afraid to say no to a client. When people come to Arroyo seeking investment money, he said Highmark tells him no five times before telling him yes once.

“He’s not a guy who says he can make me a bunch of money off my money, he’s a guy who says, ‘I will protect you from the rest of the world trying to sell you something that might not be accurate.’ He’s more like a watchdog,” Arroyo says.

Highmark said he’s lost one client in 23 years by saying no. A baseball player who was in the twilight of his career wanted to buy a $4 million house with his wife. He had a one-year contract paying about $1 million, and had $400,000 in the bank and five young children.

Highmark said no; the client said yes and quit FineMark. He lost the home to foreclosure a few years later, Highmark said.

The amount of money athletes make has changed over the years, but FineMark’s model hasn’t. It’s never advertised.

“We don’t have to,” Highmark said.

It gets its clients through referrals. About 50% come from agents, 40% from fellow athletes and 10% through accountants, Realtors and attorneys.

Nobody works harder than Highmark, said Nordqvist, who has lunch with him weekly when both are in the Phoenix area. “He’s like a father figure,” she says. “I go to spend half an hour and sit in his office and pick his brain. I’ve learned so much from him about life. He’s a role model for me.”

Clients also talk about Highmark’s competitiveness: He loves to compete with them in everything from checkers to pickleball.

“Dave is a competitive guy, that’s what’s partially so beautiful about him. He lives his life thinking like an athlete and always wants to compete with people,” Arroyo says.

“He’s not a guy who’s always talking about how much money he is going to make you. He wants you to have a stable, comfortable, peaceful, kind of angst-free idea of what’s going on with your money—because he wants to concentrate on beating you in pickleball.”

FineMark Sports Management

Formed: 2012

Home: Scottsdale, Arizona

Clients: 293

Athletes: 243

Coaches, caddies, executives, officials: 50

Clients in the U.S.: 228

Clients in Florida: 38

Broken down by sport:

Men’s golf: 90

Women’s golf: 35

Baseball: 75

Hockey: 23

Football: 11

Tennis: 3

Basketball: 6

Notable clients: Hale Irwin, Anna Nordqvist, Madelene Sagstrӧm, Azahara Muñoz, golf; Bronson Arroyo, baseball; Josh Doan, hockey; Justin Sands, Bethanie Mattek-Sands, tennis