Sympathy for the Rich Man

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.