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Sympathy for the Rich Man 

Dan Gilbert gets an education from the NBA.

What can you buy with a few hundred million and a dream? Marketing magnate Daniel Snyder bought the Washington Redskins and reserved parking on annual Worst Sports Owners lists. Peter Magowan, a grocery-store mogul, bought the San Francisco Giants and the right to be vilified for both protecting and disrespecting a famed steroids junkie.

Here in Cleveland, Larry Dolan dropped $320 million, only to discover with every flip of the sports page what a cheap son of a bitch he is. Randy Lerner earned the same right by simply inheriting the Browns from Dad.

Call it the fate of sports owners, the relatively anonymous billionaires who spend all that money for fame, fun, and the chance to be lionized on city streets, only to find that -- unless you win that rare championship -- you've simply purchased loathing rights for an entire region.

Of the 120 or so owners in the four major sports, perhaps only a dozen earn the affection of fans. The best earn titles, providing them with automatic glory until the winning years run out, when they're once again cast into the fiery pits of radio call-in shows. The smart stay anonymous, preferring the low profile of luxury boxes, allowing their general managers to take the heat. But most can't resist that fame, that temptation to touch the flame, where the odds are roughly 30-1 that they'll get burned, badly.

Gordon Gund did it right. In 1983, he paid $20 million for the Cavaliers, rescuing them from Ted Stepien, who gave away top draft picks as if they were Brook Jacoby trading cards. "You don't have to know a lot about NBA basketball to know that if your team is on the bottom of the league and has four years with no first-round picks, you're in deep trouble," Gund says today.

So he saved the team -- ushered it into a new downtown arena, built it to the verge of a championship, then quietly guided it through the lean years. He loved it, but showed his devotion from afar, taking a page from the book of Philip Wrigley, who preferred working in the yard to witnessing his beloved Cubbies lose. Gund couldn't watch his team anyway. He's been blind since age 30 and had built a life in New Jersey.

They called him an absentee owner. That was how he liked it. He may have missed out on glory rightfully his during the Nance-Price-Daugherty years, but he also insulated himself from the wretched era when he was forced to ask Clevelanders to pay to see Ricky Davis, Michael Doleac, and Bimbo Coles.

In 2004, he finally found a convenient departure. The Cavs had misfired their way to the bottom of the NBA, winning the right to draft hometown star LeBron James. He alone would generate wins and revenue, begin to fill an arena where the crowds had become smaller than at St. Ed's football games. But it would take some aggressive fathering to rebuild once again. At 65, Gund wasn't interested. "It was time to put the franchise in stronger, perhaps younger hands," says his close friend, NBA commissioner David Stern.

There was also a strong incentive: By the time Gund put the team up for sale, it was worth $375 million -- almost 20 times what he'd paid for it. So he went looking for someone with a few hundred million dollars and a dream. Dan Gilbert had both.

Gilbert, 44, is a hybrid sports owner model. He has Art Rooney's working-class pedigree, Dan Snyder's love of spending, Mark Cuban's love for e-mail and disdain for suits. But when Gund put his team up for sale, none of that mattered as much as one attribute, the quality shared by all modern-day owners: He was obscenely rich.

"It's kind of the typical thing," Gilbert says. "You realize in high school, 'Most likely I'm not going to be a professional athlete. So one day, I'll buy a team.'"

Of course, such thoughts aren't remotely typical. Long gone are the days when Art Modell could put up $250,000 for a controlling share of the Browns, or Bud Selig could buy the Milwaukee Brewers with the savings from his car dealership. Today, you need the net worth of a Baltic state to qualify. Not even Tiger Woods, the world's richest athlete, makes Forbes' list of the richest Americans. Compared to that of their owners, the wealth of most professional sportsmen is downright average.

Gilbert, however, is the founder and chairman of Quicken Loans, the nation's largest online mortgage company. He has amassed enough wealth -- just over $1 billion -- to qualify for entry into one of America's most exclusive and quirkiest clubs: the pro-sports owners society. So on March 1, 2005, alongside his newest employee, LeBron James, Gilbert was introduced as the owner of the Cleveland Cavaliers.

What did his $375 million buy him? Gilbert is convinced it will eventually yield what most owners crave: a championship. And he might be right. But even for the obscenely rich, there is a learning curve. And before long, Gilbert was opening the papers to read things he never heard in the mortgage business.

"He had some embarrassing times in the early going," Gund says. "It's a whole new way of doing business. Very different from a mortgage company."

Stern spent Opening Night 2004 at the Palace in Detroit. It was a logical place to be. The Pistons had won the previous season's title, knocking off the favored Lakers. But Stern had other business too. Dan Gilbert had expressed interest in buying the Cavaliers. Stern wanted to meet him.

Two years later, it's odd that Gilbert's reign as Cavaliers owner began in the Palace, the very building where his team was bounced from the playoffs last spring. But for Gilbert, it made perfect sense.

He had grown up in Southfield, a working-class Detroit suburb. As a boy, if he wasn't fooling with the adding machine in the basement of his father's bar, he was at the old Cobo Hall, watching Bob Lanier and Dave Bing. The hometown teams -- Pistons, Tigers, Lions, Red Wings -- were among his chief providers of joy and angst. "I got excited about two things as a kid," he says. "Sports and business."

But it was his "golden gut" for business that earned the eye, and the ire, of adults. At 12, Gilbert built a home pizza delivery store, using kids on bikes to hustle store-bought pizzas to neighborhood families. Only when the real pizza shops alerted the health department was he forced out of business.

In high school, Gilbert says, his entrepreneurial spirit landed him in the principal's office; the school didn't appreciate his cutting into their candy-sales business. At Michigan State, that same spirit landed him in even hotter water when he was arrested for running a football-betting pool. He said later that no money changed hands; the cops thought otherwise. Gilbert was sentenced to 100 hours of community service.

In college, he studied sports journalism, then spent six months as a reporter for a Kalamazoo TV station. But sports were something he could only watch, think about, talk about. Gilbert needed something he could do.

He enrolled in law school at Wayne State and started selling real estate on the side. He started by putting a for-sale sign on his parents' home. That the house wasn't for sale was only a small obstacle, easily hurdled with Gilbert's wit and natural gift for sales. He just shook their hands and showed them to a home that was.

But after a few months, Gilbert realized the real money wasn't in selling houses. It was in lending the money to pay for them. So with savings and a $5,000 bank loan, Gilbert founded Rock Financial, a one-room mortgage company.

It turned out that hustling mortgages was a lot like hustling pizzas. Gilbert hunted down young, eager Detroiters and promised they would succeed if they followed his lead. Athletes were particularly receptive to his message: Patrick McInnis, who played football at Eastern Michigan, and Bill Emerson, who played on a national championship football team at Penn State, started on the same day. Both are now executives with the company and speak of Gilbert like they might a beloved coach. "He had a strong desire and will to win," Emerson says. "He was very motivated. Very high energy."

Shawn Krause, another Quicken employee, was working at a rival mortgage company when Gilbert decided he wanted her. "Dan called me up three times, and I kept hanging up on him," she recalls. "I'm happy where I'm at, dude," she would say. He finally pursuaded her to come see the office, and he sealed it by inviting her on a company outing: a nasty game of WhirlyBall. She's been working there ever since.

From his one-room operation, Gilbert built Quicken into a monster. The company's sales floors in Livonia, Michigan, now hold hundreds of people, divided into teams like the Senior Tour and A League of Their Own. Scoreboards hang above the floor, tracking the length, volume, and result of their calls.

"They have a very 'rah-rah' internal culture," says Cindy Goodaker, editor of Crain's Detroit Business. "Not everybody likes that. But if in you're sales . . . you usually do."

The ones who succeed talk about the place as devotees, not employees. "They have a very cultish mentality over there," Harry Glanz, a former Quicken employee who runs his own Michigan mortgage company, once told Crain's. "It works very well for them . . . but don't drink the Kool-Aid."

Employees learn quickly whether or not they'll fit. The job begins with a day-long orientation led by Gilbert. That's where he introduces his charges to his book of "isms," a manual filled with axioms peeled from the pages of Howard Schultz biographies and Tony Robbins speeches.

"Numbers and money follow; they don't lead," it proclaims, and "Responding with the sense of urgency is the ante to play."

The book also suggests a leader who doesn't rule from the shadows. "WE RETURN ALL PHONE CALLS TO EVERYONE EVERY TIME," reads a company-wide e-mail Gilbert sent. "Some of you have CHOSEN to ignore this most basic philosophy . . . YOU CANNOT AND WILL NOT WORK HERE ANYMORE. . . I will find you. I will personally 'root you out.'"

If they survive orientation and the hundreds of training hours that follow, salespeople are rewarded with salaries averaging $80,000 and perks that make the place seem more funhouse than mortgage house. Aside from free food and slushies, Emerson gives out concert tickets over a PA system every "Ticket Window Thursday." A company rock band, Rate Lock, plays corporate functions. When the band competed at a corporate rock-off in Cleveland, Gilbert bused 200 employees to the competition and put them up in hotels. For the company's 20th anniversary last year, he bused 5,300 people -- employees and their families -- to Cleveland for a private party headlined by the Black Eyed Peas and attended by Kid Rock. One of their many sales contests sent 400 people on a four-day cruise in the Bahamas. Quicken has been on Fortune's list of Best Companies to Work For three years running.

And the money, as Gilbert would say, has followed. He built Rock Financial into one of the country's largest independent mortgage banks and took the company public in 1998. He launched a year later, then sold the company to California-based Intuit for $370 million. After Intuit renamed the company Quicken Loans and expanded it even further, Gilbert bought it back. It's now the country's 15th-biggest mortgage bank, closing $16 billion in loans last year, and it's the nation's top online seller of mortgages.

In recent years, Gilbert, a hands-on, head-first leader, has scaled back his role at Quicken so he could invest elsewhere. He's poured money into everything from Fathead, a company that produces sports memorabilia that sticks to walls, to Bizdom U, a school for aspiring entrepreneurs, to Camelot Pictures, his brother's Hollywood production company and the financier of 2004's Garden State.

But even a Hollywood hit barely launched Gilbert onto the pages of his hometown newspaper, and he has remained, despite his enormous wealth, a relatively anonymous figure in Michigan. It was just a few years ago that, while dining in Detroit, a server who noticed the name on Gilbert's credit card remarked, "You work for David Hall, right?" She was referring to Gilbert's regional vice president. "That's right," he said.

But a few months after meeting Stern, he went from anonymity to the pages of Sports Illustrated, The New York Times, and the New York Post. And the words wouldn't be kind.

The first owner to welcome him to the NBA was a fellow fortysomething billionaire who made his fortune during the dot-com boom: Dallas' Mark Cuban. As children of the '90s' New Economy culture, they shared a fondness for denim, Blackberries, lavishing their employees, and generally doing things that would make their corporate forefathers spill their Dewars.

It was no wonder, then, that some of Gilbert's earliest moves as owner appeared ripped from the playbook Cuban used when he bought the Mavericks in 2000. Cuban famously bought his players fluffy, monogrammed bathrobes; Gilbert went with softer towels. Cuban installed plasma TVs in the Mavericks' locker room; Gilbert bought TVs and Xboxes. Cuban upgraded the team jet; Gilbert ensured there would be fresh-cooked waffles and omelets on road trips.

But there was one distinct difference: Cuban's team, a perennial loser, quickly started winning. The Cavs were 31-23 when Gilbert took over, in position to make the playoffs for the first time in six years. But they quickly went into a tailspin.

Later, Sports Illustrated would report that coach Paul Silas wanted out after his first 45-minute meeting with Gilbert. He certainly coached like it. He began using unpredictable rotations, butting heads with genial veteran Eric Snow, and benching starting point guard Jeff McGinnis for an entire game. "It was spinning out of control," Gilbert recalls.

So three weeks into his tenure, Gilbert rooted Silas out, opting to eat the $8 million left on the coach's contract in hopes of salvaging the season. After he booted Silas, reports surfaced that Gilbert fired the veteran coach in a hallway and that he had been passing notes about the rotation to the coaching staff during games. No one quite believed them, but they stung Gilbert. So did Plain Dealer columnist Roger Brown's sourceless report that Gilbert offered to fly LeBron James' mom to away games on his jet, a clear violation of league rules.

"I had never met his mother," Gilbert says. "I didn't even know what she looked like. A lot of the stories were outright fabrications. That was a surprise. I always thought they embellished."

The season ended with the Cavs out of the playoffs. It was a remarkable collapse. Gilbert responded by firing General Manager Jim Paxson and went looking for someone else to make use of what would be $28 million of salary cap space that summer, enough for a hearty shopping spree. But he set his sights on a curious target: Pistons coach Larry Brown.

Never mind that Brown, a famously brilliant but obstinate basketball mind, had no experience making personnel decisions. And when Gilbert and Brown began discussing a front-office job, Brown's team was still playing in the Eastern Conference Finals.

It was all typical Gilbert: With Silas, he was simply applying his "no boundaries" approach to management, refusing to let his inexperience in sports management color the fact that Silas, in his estimation, wasn't getting the job done. Brown was just another competitor Gilbert wanted on his team.

But soliciting an NBA coach in the middle of a playoff run isn't the same as courting a loan processor. The papers skewered him. "Can Gilbert be that stupid?" the New York Post asked. Sports Illustrated columnist Ian Thomsen described a "growing impression around the league that Gilbert may ruin what looks to be a good thing in Cleveland."

"Dan just didn't know enough about the league to be able to make a fair opinion," Thomsen says now. "It was not a promising thing for a guy to come into the league and, based on his own first impressions, draw conclusions."

Conventional wisdom dictates that owners should make key hires and then disappear. But rookie owners often "insert [themselves] in the process more often than [they] should," says Tom Wilson, longtime president of the Pistons. "The key thing is finding someone you trust and then putting a sock in it."

After the deal with Brown fell through, Gilbert found a viable candidate for that role: Danny Ferry. After two years in the front office of the annually contending Spurs, the former Cav was considered a rising front-office star. But Gilbert's early reviews nearly cost him his chance at Ferry. "I walked into my first meeting with a lot of doubt," Ferry recalls. "I had read the newspapers and internet, and I figured this guy was a little nuts."

But Ferry found Gilbert nothing like the media's portrayal. "I walked out of the meeting with a confused feeling," Ferry recalls. "I really liked him."

Gilbert, it seemed, had learned that not every axiom translates from mortgages to basketball. "Dan was a little bit naive," says Stern. "And he got a quick education."

If there's a Quicken Loans "ism" that doesn't fit into his life as NBA owner, there's only one, Gilbert says. It's that whole "no boundaries" thing.

"At Quicken and Rock, we have a no-boundaries philosophy, where anyone can talk to anyone else, anytime, about anything," he told a Detroit reporter during last year's playoff run. "But with the Cavs, a kind of bunker mentality sets in with the coaches and players during the season. You can't have distractions. The owners and the other people in the organization have to respect the sanctuary of the player-coach relationship. There are big egos involved, and some of them are sitting on the bench. It's very delicate."

Still, he's built an obvious bond with Ferry. The towering GM passed through the front offices a few weeks ago while Gilbert was being interviewed by a reporter. "Why are they talking to you?" Ferry joked.

"You look like a middle school history teacher in that outfit," Gilbert fired back.

He also stays in touch with his players, though perhaps cautiously. Forward Donyell Marshall says Gilbert sent e-mails on Marshall's wedding anniversary and his son's birthday. "He's probably the only owner I know that I've had in my Blackberry," says Marshall, who's played on six teams in his 13-year career.

While early reports described Gilbert and his partners, including R&B hitmaker Usher, "hanging" with players, Gilbert rarely sees them these days. Players say they occasionally see him before or after a game, but that's about it. During a practice two days before Opening Night, Marshall had the unusual occasion to talk to the boss. It was "the first practice I've actually seen him at in my two years," he says.

If Gilbert labors to keep out of his players' way, he tries just as hard to make his other employees know he's there. He may not be in the team huddles like Mark Cuban, but he's no Gordon Gund either.

When the Cavs sale was finalized, VP of Sales Chad Estis started calling friends in Detroit. "Brace yourself, because it's going to be fast and furious," he recalls hearing. "They're going to come in and look around and make some fast and immediate improvements."

That was clear at the first company meeting, one employee recalls. Gilbert, a pop-culture junkie, asked a woman what her favorite movie was. When she told him Risky Business, Gilbert asked whether that was the movie where Tom Cruise dances in his underwear. It is, the woman said. Gilbert then said something few businessmen would: "I'll give you a 10 percent raise if you come up there and do it right now." She didn't do it, but the message was clear: Times were changing.

Gilbert still spends most of his time in Detroit. In the off-season, he occasionally makes the 30-minute flight to check on projects or meet with Cavs employees. He's obsessed with aesthetics and likes to roam the arena, making sure things are bright and clean. "That's gotta go," he said on a recent morning, after discovering a small patch of ugly carpet near the arena floor. When an employee pointed out that it was actually new, Gilbert shot back playfully: "You just killed me. That ruined my day right there. That's my mother's house from 1978!"

During the season, he watches almost every game from his seat behind the public address announcer; the owner's loge, he says, is too distracting. When the game ends, it's right back to the plane, back to his wife and five kids in suburban Detroit.

But when he is in town, he makes an impression and leaves Cavaliers employees talking as if they've been drinking the same Kool-Aid as the folks in Michigan.

"Dan comes rolling in, and he's hysterical, he's lighthearted, he's engaging," says Tracy Marek, who started with the Cavs under Gund and, like most employees, kept her job after Gilbert took over. "He's always trying to get you to act out scenes [from movies]. It catches you completely off guard. You don't know what to do with it, but you learn it's OK to be Al Pacino for a second and then turn around and do your best Julia Roberts."

Marek runs game presentation, which Gilbert is obsessed with. In a way too few sports owners seem to, Gilbert understands that the game itself attracts only so many customers. On any given night, the entertainment on the court can be unmemorable. And unmemorable doesn't keep customers coming back. Every time the team can interact with the fans -- by embarrassing them on the big screen, dropping a lottery ticket from the sky, shooting them a free T-shirt, or allowing them to text message friends on the scoreboard -- he's bound to come back. Chances are good he'll bring his wallet.

So during most games, Marek gets an e-mail from Gilbert pointing out things that could be better: The music's not upbeat enough, or mascot Moondog needs to work the crowd more. Anything to keep the fans in the arena.

Marek also learned the fun way Gilbert's penchant for rewarding employees. Last season, she thought her staff hadn't spent enough time with the owner, so she asked for a meeting. Instead, he flew 15 people on the team plane to Detroit to watch a Pistons game. "It was crazy cool, because it was the plane," Marek says. "Whoever gets to go on the plane? It was way above and beyond the call of duty. To him, it's second nature. To us -- we were blown away."

Most of what he does can fit neatly into one of his isms. But he also seems to simply enjoy shaking people's perception of how a billionaire sports owner should act.

When he speaks to businessmen, which he does often, he shows a video of a trip he once took to a pumpkin patch. The patch's entrance had a sign that read "Pumpkin Patch," with an arrow pointing away from the patch. So Gilbert broke out his cell phone and recorded an interview with the kid running the patch that day. The kid, of course, had no idea why the sign was pointed the wrong way, nor did he intend to fix it.

The video illustrates one of Gilbert's key isms: "Always raising our level of awareness." But it also gets a big laugh and shows Gilbert for what he is: a dorky dad trapped in a mogul's body.

On Opening Night, an hour or so before tip-off, Gilbert arrived at the offices of Cleveland Cavaliers TV, just down the hallway from the team's locker room. CCTV is a bunker loaded with TV monitors, editing equipment, and the like; it's where everything that appears on the main scoreboard is produced. Gilbert's fellow investors were waiting upstairs for a presentation. But he wanted to see the video that plays when the Cavs' starting lineups are introduced.

Johnny Greco, an energetic 27-year-old, nervously rolled the video. Gilbert watched, transfixed. "Does it still have Damon tapping his head?" Gilbert asked. A moment later, Damon Jones emerged from a luxury car and tapped the top of his hair, as if checking it in a mirror. "Great," Gilbert said. The video ended. "It's perfect," Gilbert said, giving Greco an enthusiastic high-five.

Gilbert's staff was still waiting to walk him upstairs, but he told them to hold on. "I gotta tell him this one thing," he said, turning to Greco. "What was that movie with those two African American brothers?"

He was talking about the Wayans brothers and Little Man, a movie in which a tiny jewel thief poses as a baby. "It was awesome!" Gilbert said, smiling. "It would be perfect for when the other team is complaining."

It's hard to say what motivates the obscenely rich to buy pro sports teams. Most earn their fortunes anonymously, and buying a team instantly makes them known. But few are willing to admit that they're in it for the notoriety, and they likely would sum it up like Gordon Gund does: "It goes with the territory."

Of course, there's also the chance to become even more obscenely rich. Gund certainly did -- something he's not afraid to admit.

Then again, maybe that's not it at all. Maybe it's that sports is the one business in which making money doesn't mean you're successful. They've made their money, after all. Anyone can be rich. Succeeding as a sports owner is a much steeper mountain to climb, and not many reach the top. "If everybody took their turn," the Pistons' Wilson points out, "you'd win three times a century."

That's a statistic not lost on Gilbert. "Three-point-three percent of teams win a championship each year," he says.

Gilbert seems genuinely thrilled about bringing a championship to Cleveland. No, it's not his hometown. But he's fond of hard-luck midwestern cities; before he bought the Cavs, he lost out on a bid to buy the Milwaukee Brewers. He's quick to disparage coastal metropolises and their workforces, which he truly believes are egocentric. And he brags that his 150 Cleveland employees -- he opened a satellite office here last year -- are among the top producers in his company.

Anyhow, when the team starts stinking, he can still hide out in Detroit, and his kids don't have to hear about it at school -- his own little play from the book of Gund. "If your basketball team sucks, you're an idiot," Wilson says. "It really beats you down. It's hard to be that successful in life and open up the newspaper and find out how much you suck."

Gilbert seems aware of his main duty, the one thing that will keep his championship odds above 3.3 percent: keeping LeBron James at any cost. He's dumped $12 million into the Q, even though investors bristled at his spending millions on replacing the blue seats with burgundy ones. And he's building a $20 million practice facility in Independence, closer to James' home, even though some city leaders thought he owed it to Cleveland to build the facility downtown, where the city could collect property and income taxes.

Both investments -- along with the millions more he plans to spend on making the Q an entertainment destination -- make Cleveland a more desirable place to play basketball. That makes it harder for James to ditch his hometown for the neon billboards and bigger endorsement dollars in New York or L.A. And if James is around, well --

"Maybe I'm naive, but I believe in every bone in my body that we will win a championship," Gilbert says. "I just know it.

"We'll see, though," he adds, as if recalling how quickly the press can pounce. "It's all words until it happens."

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