Mark McCormack was forever trying to sign Billie Jean King as a client. She was forever telling him no.

It was the 1970s, when King was one of the top female athletes in the world, and McCormack was starting to achieve his legendary status as father of the sports business industry. Founder and CEO of IMG, McCormack dominated the golf business; he wanted to expand into tennis.

“Mark had been chasing me for years,” King said. “He kept coming to me and saying, ‘You should really be with us. We are big. We are this. We’re that.’”

Beginning in the tennis division, Bob Kain spent 30 years at IMG, ultimately taking over as co-CEO after Mark McCormack’s death. In this picture, Kain holds a classic Donnay racquet played by his client, Bjorn Borg.tony florez photography

King eventually did sign with IMG, but not with McCormack. She signed with a young agent who had just started with the company, Bob Kain. 

“I went to IMG because of Bob,” she said.

Kain joined the company and started representing tennis players in 1976 when he was in his mid-20s. He spent the next 30 years there, going on to run the tennis division, creating several other businesses for the company and eventually becoming co-CEO after McCormack passed away in 2003.

“Mark anointed Bob and that should tell you everything,” King said. “He knew he’d leave it in good hands if something happened to him.”

While McCormack was the king of IMG, Kain was the power behind the throne. In many ways, he was IMG’s secret weapon — secret primarily because he never promoted himself.

“Bob never brags about himself,” King said. “Ever.”

Save for a short blurb in the 1980s when Tennis Magazine declared him the second most powerful man in tennis behind McCormack, Kain has never been featured in a publication. That’s somewhat surprising considering the impact he’s had on the business, not to mention the respect he garners across the industry, including from longtime competitors.

“Bob Kain is one of the most under-recognized pillars of the sports marketing industry,” said Rocky Hambric, who has been a golf agent competing against IMG for 40 years.

Kain also has been a mentor to many, including Mark Steinberg, Tiger Woods’ agent, who started his career at IMG and reported to Kain when Steinberg ran the golf division.

“Bob was a great leader in that he let you learn from your mistakes and didn’t crush you when you did [make mistakes], and I made plenty,” said Steinberg, now a principal in Excel Sports Management. “There is no way IMG would have been what they were or where they are now without him because of his leadership. Outside of Mark McCormack, I don’t know if there was a more critical and important figure in the company — and in the industry — for all those years.”

Since leaving IMG in 2006, Kain has advised leaders throughout the industry, including billionaire investor Randy Lerner when he owned the Cleveland Browns and Aston Villa, and Creative Artists Agency in the early days of CAA Sports.

“Bob Kain helped shape the sports representation business as we know it today,” said CAA President Richard Lovett.

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These days, Kain lives in paradise — and everyone likes him there, too. When you approach the gate at the La Quinta, Calif., community where he lives and say who you’re visiting, the security guard beams.

“Bob Kain is the Winston Churchill of The Quarry,” he says and waves you in with a flourish.

Kain is waiting outside his house. He’s 69 but doesn’t look it. Fit, trim and relaxed, he’s one of those people whose age would be hard to guess. There’s a calm confidence about him that immediately puts you at ease.

His wife, on the other hand, is bursting with energy and equally as charming. Kain is married to Rosalynn Sumners, the former world champion, three-time national champion and Olympic silver medalist figure skater. She’s beautiful, bubbly and vivacious, the yin to Kain’s yang.

His house looks like a movie set. A deep, blue pool is right off the patio. A duck pond — yes, with ducks on it — is just beyond the pool. And beyond that is the bright, emerald-green La Quinta Country Club golf course, right in Kain’s backyard, where the PGA Tour plays the Desert Classic. “It’s the best golf course in the desert,” Kain said. “We wanted a place pretty and quiet.”

Sometimes he can see Bighorn sheep, an endangered species, strolling on the golf course from his patio.

When Kain sits down for the interview, he’s prepared. He has notes written on a yellow legal pad of most of the major moments in his career, starting 40 years ago when the sports industry was young. There were a lot of them.

“I went to work for IMG in 1976 and IMG was basically a golf company,” he said. He was the second or third person hired in tennis, and while he started as an agent, he ended up running and building a division well beyond representing athletes.

When he got there, IMG had a few tennis clients and represented Wimbledon, but not much else. “The gross revenue of the tennis division in 1976 was under a million — about $600,000 or $700,000 were the gross revenues,” he said. “And when I left it was about $150 million.”

He started out by signing players. Virginia Wade was a client, along with King. Vitas Gerulaitis, who won the 1977 Australian Open, signed with Kain. He then represented Bjorn Borg, who was the No. 1 men’s player in the world when Kain was in his late 20s. In later years, he also represented Chris Evert, Pete Sampras and Andre Agassi, to name a few.

While Kain was at IMG, the agency represented 11 of the top-ranked men’s tennis players in the world, as well as 10 women’s world No. 1s. But Kain was not content just to sign and represent players. He wanted to branch into events and associations.

IMG already had Wimbledon because McCormack had signed it — “Wimbledon was his baby,” Kain said — but under Kain’s leadership, the company signed the three other grand slams — the U.S. Open, Australian Open and French Open. “We helped build them,” Kain said. “And when I say build them, we did their sponsorship programs and we sold their television rights worldwide.”

In addition, IMG signed the ATP Tour and the WTA Tour, and it owned and operated two other tennis tournaments, the Miami Open and Indian Wells.

“We went from nothing in tennis in my 25, 30 years, to representing so many No. 1s, all four grand slams, the ATP and the WTA — both tours — and owning the two biggest tournaments in the world outside of the grand slams,” Kain said. “Grand Slams you can’t own because they are owned by governing bodies. So that, to me, was complete domination. And obviously, I didn’t do it alone — but I spurred it and led it.’”

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“Mark McCormack — you asked me about him,” Kain said while sitting on his patio. “The reason I got close to him is I built a business almost as big as the golf business and he really didn’t know anything about tennis.”

McCormack didn’t hire Kain. Bud Stanner, one of IMG’s earliest employees, hired the young Kain. But McCormack got to know Kain early on in his career.

One of Kain’s first big signings was Gerulaitis, who was then ranked No. 4. Kain was a tennis player himself, having played at the University of Virginia (see story), and they hung out with Bjorn Borg, who was No. 1 in the world.

“Borg loved Vitas,” Kain recalled. “And Borg, who was a client of IMG, walked in and told McCormack, ‘I want Kain to manage me.’ McCormack said, ‘He’s too young.’ And Borg said, ‘No, I want Kain,’ and that really helped me.”

McCormack was an attorney who required all the executives to wear jackets and ties to work. McCormack used to schedule breakfast meetings for 7 a.m. at the Union Club in downtown Cleveland and would always order an English muffin burnt black, Kain recalled.

“Eight out of 10 times a guy would bring it back crispy and he’d say, ‘I told you I want it burned!’” Kain said. “And then they’d bring it back.”

Kain’s impact on the sports industry is undeniable, if not somewhat quiet, with CAA President Richard Lovett saying, “Bob Kain helped shape the sports representation business as we know it today.”tony florez photography

McCormack was known for his prodigious work ethic, traveling 200-plus days a year. “He was an unbelievable workaholic,” Kain said.

McCormack was known for his vision, for seeing trends before anyone else. But Kain said McCormack had a couple of other things that set him apart. He always thought globally when no one else in the U.S. sports business was thinking that way. “He used to say, ‘Sports doesn’t have a language.’”

And unlike most visionaries, McCormack paid attention to detail. “You’ve met these millionaires and billionaires. Most of them fly at 20,000 feet. They don’t get into the details,” Kain said.

But McCormack could tell you every detail of every sponsorship of a client like Wimbledon, and he had it all written down. He was the same way with athlete clients.

“He taught us you were never too big to manage your client,” Kain said.

At the same time, he had a driving ambition to build the biggest sports empire in the world, and he gave his executives free rein to pursue new opportunities and build businesses. It was the perfect place for Kain. “I like taking things from very small and trying to grow with them,” he said.

In the early 1980s, Kain had an idea. He thought that ice skating was a business that IMG should get into. He tried to sign his now wife when she was 18, but she turned him down (see story). Undeterred, Kain recruited Scott Hamilton, who had just won gold at the 1984 Olympics.

“I just instantly, instantly liked him,” Hamilton said, adding that he signed with Kain after their first meeting.

In those days, there weren’t a lot of opportunities for professional skaters. There was Disney on Ice, which Kain and Hamilton didn’t seriously consider because he’d have to wear a costume, and there was Ice Capades. Kain negotiated a two-year deal with a third-year option for Hamilton with Ice Capades. Hamilton was happy and was being paid more than the other skaters.

As the third-year option was coming up, Kain told Hamilton that Ice Capades wasn’t extending him.

“I go, ‘Why?’” Hamilton said. “And he said, ‘They are going through a sale and the new owner only wants female skaters. He doesn’t want any male skaters.’”

Hamilton said it was typical of Kain to be up front with bad news but then to immediately offer a solution. “Bob said, ‘I’ve got an idea. Do you want to help us start a tour?’” Hamilton said. “And I said, ‘Well, let’s see. Let me check my schedule. I am kind of unemployed.’ At that point skating had really taken off in popularity and Bob said, ‘Let’s work on this.’”

IMG launched Stars on Ice with Hamilton as its premier attraction in 1986. It started out small. The first show in Philadelphia brought in $45,000 in revenue, and early on the skaters traveled on a school bus. Ten years later, the Philly show brought in $1 million, and the tour ended up with its own private plane. There were skating shows that ran on television, up against football and basketball, from November through March.

“What I am proud of is Scott and I … we created the tour,” Kain said. “And at the time everyone was skating with the Smurfs or Mickey Mouse, there was no serious tour for great skaters. These were great Olympic athletes and they were skating with cartoon characters. So we totally changed the world for professional skaters.”

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In 1987, IMG represented the top tennis players and top tennis tournaments in the world. “We were No. 1 in representing tennis players and No. 1 in events,” Kain said. “So what else can we do?”

At the time the top tennis coach was Nick Bollettieri, who had a training academy in Bradenton, Fla. Kain went there to visit him.

“At first he said, ‘I want you to represent me,’” Kain recalled. “And I said, ‘No, but we want to buy you.’”

So IMG bought the Nick Bollettieri Academy, which at the time was 27 acres, mostly covered by tennis courts. But Kain had a vision. He knew the parents of aspiring tennis players were no different than the parents of aspiring athletes in other sports, so he expanded the Bollettieri center into what is known today as IMG Academy. These days, it produces the best young athletes in a host of sports: baseball, basketball, football, golf, lacrosse, soccer, tennis, track and field and cross country.

“I made it into 280, 300 acres — golf, tennis, football, soccer, fitness,” Kain said. “And made it multisport and made it the biggest elite training academy in the world. From nothing. From a bunch of tennis courts and Nick.”

His next big target came in 1992, when Kain went to McCormack and asked if he could build up IMG’s modeling business. At the time IMG Models consisted of a few marginally known models and was losing money, Kain said. “IMG had a little modeling agency that McCormack started long before, but we all kind of laughed at it,” he said. “It was under a million bucks.”

Kain enlisted Chuck Bennett, who was then working in the tennis division, to run IMG Models. “Basically, he came to me and said, ‘Would you do this? We are going to make it work or we are going to close it,’” Bennett recalled.

Their first break came in February 1992, when IMG signed supermodel Niki Taylor. IMG Models went on to sign Heidi Klum, Tyra Banks, Kate Upton and Gisele Bündchen. Then, as Kain put it, “we IMG-ized it.” IMG bought New York Fashion Week, created Singapore Fashion Week and Sydney Fashion Week, and began representing Milan Fashion Week.

“We went from representing nobody you ever heard of to being No. 1 in the world,” he said.

Part of IMG’s successful equation was that McCormack had a knack for hiring smart, young people, teaching them the business and then giving them autonomy to do things like what Kain did with IMG Academy and IMG Models.

“We really had fun,” said Peter Johnson, who built IMG’s team sports business and succeeded Kain as CEO of sports and entertainment when Kain left the company in 2006. “Our culture was a culture of hiring the best people we could and it was about winning, it was about friendship.”

Like Kain, Johnson was hired by IMG in 1976 when he was 25. They had a friendship that has spanned more than 40 years.

In the history of the sports agency business, a lot of powerful firms have broken up. More often than not, one of the contributing factors has been clashing egos. But IMG avoided that while McCormack, Kain and others built an empire.

“If it wasn’t for Bob — who I always thought was the glue that kept IMG together in those early years — there were a number of people who would have left,” Johnson said. “Because he was a fair guy, and without him it would have been a different story.”

Having been an adviser across the industry after leaving IMG in 2006, today Kain primarily works on his +2 handicap.tony florez photography

During IMG’s heyday, only two top executives left — Ian Todd, who had been IMG’s head of European operations, left to become a top marketing executive at Nike, and Sean McManus left IMG’s powerful television production arm, TWI, to become president of CBS Sports.

McManus said he often sought Kain’s advice. “He had incredible institutional knowledge about sports marketing, partially because he was one of the men who actually created the business of sports marketing and grew the business of sports marketing,” McManus said.

Kain has a combination of skills that make him a great leader, McManus said, including being creative and innovative, while having strong interpersonal skills and unflinching integrity.

“Bob Kain could have run an automobile company,” he said. “He could have run an investment firm. He could have run pretty much any kind of company in the world if he put his mind to it and wanted to learn it. He was just that good an executive and that respected an executive that I could see him running American Express, I could see him running General Motors or I could see him running Apple computer.”

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“There is no better gentleman in the world of sports business than Bob Kain,” Hamilton said. “You can ask any athlete in any sport who has worked with Bob Kain and they will tell you. Bob is a gentleman.”

Evert signed with Kain when she was 24 after her father, who had managed her career since she was 18, turned down countless other agents. Kain was the only one her father trusted and liked, she said.

“There’s nothing not to love,” Evert said. “There are no character flaws in that man. He’s so aware of people and their feelings, and yet he’s a brilliant man.”

McManus said Kain’s clients — whether it was an athlete or an executive — trusted him. “He was one of those guys that if he said something, you could take it to the bank,” McManus said.

Kain’s likability had value for IMG, as well. The company’s dominance angered a lot of competitors. According to Sports Illustrated in 1990, McCormack’s nickname was “Mark the Shark,” and IMG was “the company people love to hate.”

“You know what happens when you dominate any business,” Johnson said. “People don’t like you. People don’t like Alabama. People hate the New England Patriots. A lot of that was Mark McCormack. And IMG was always very, very successful with always hard-driving executives. And Bob was, you know, a little bit different. That really helped the image of IMG.”

Stephanie Tolleson was a former pro tennis player who IMG hired in 1981. She was promoted to head the tennis division after Kain was named president of the Americas.

“It was a moment in time that we were lucky to live in — in terms of this industry,” Tolleson said. “The team that was pulled together that we were part of was special, but then to have the person leading it to be someone you genuinely respected was a real gift.”

Kain said he was far from perfect. One of his biggest mistakes was early in his career when IMG was starting the Miami Open. He spent too much money on it.

“I lost a million bucks at a time we couldn’t afford to lose a million bucks,” he said. “Everybody was really pissed at me. … It affected other senior guys’ bonuses.”

But McCormack wasn’t angry.

“And he wasn’t the most compassionate guy,” Kain said. “He was pretty rough at times. But he took me aside and said, ‘Don’t worry about what anybody else said. You did exactly what we should be doing. We should be forward thinking. We should be looking at owning things and you were right on target. We just got a little ahead of ourselves.’”

When McCormack died, Kain handled the sale of IMG for his family, including his wife, Betsy Nagelsen McCormack, a longtime tennis pro who Kain had represented. There were several interested buyers, and IMG ultimately sold to Forstmann Little for $750 million in 2004. It was later sold to WME and Silver Lake Partners in 2013. IMG is no longer a stand-alone company, and a lot of the people who built it are gone.

Does it bother Kain that IMG is not what it once was?

“I feel a little bad,” he said, “but you know what? You gotta get over that because life goes on and the world changes.”