Sports business titan sees long marriage for Cavs' Gilbert, LeBron
Everyone has an opinion about where LeBron James is going and who's joining him. To that point, the LeBrons from the TV commercials were alive and well this past weekend, having reportedly been in Miami, New York and Chicago all at the same time.
It's the height of silly season in the NBA, and the start of the most anticipated free-agent period in league history is still more than a day away. But one person is perhaps most uniquely positioned to speculate on LeBron's future. That person has been on both sides of the fence in LeBron's relationship with Cavaliers owner Dan Gilbert, and he also was willing to speak freely and on the record when I reached him on the phone this week. No sources, no confidants, no private moments, no agendas.
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| Dan Gilbert didn't buy the Cavaliers to watch the franchise's most valuable asset walk away. (Getty Images) |
"The irony about this whole media circus is that, if you look at what LeBron has done in Cleveland and what Dan has accomplished in Cleveland with the Cavs, I believe had they won even one championship -- let alone multiple titles over the past two or three years when they really were deemed to have a shot -- we probably wouldn't be going through this exercise," Greenberg said. "My point being, the Cavs and LeBron, Dan and LeBron, and LeBron and the Cavs are the perfect sort of triangle and match for one another and ultimately will bring a championship -- and probably multiple championships -- to Cleveland. They just haven't done it yet. And had they, I don't think anybody would be talking about going to Chicago, Miami, New York or another place. I think that has helped fuel the speculation."
There are those on the team side of things willing to speculate on their chances of landing LeBron. There are those from various, competing factions of LeBron's camp who are willing to do the same. But only Greenberg has the kind of experience as a stakeholder with both Gilbert and LeBron, so his words carry considerable weight in this breathless debate about where James will decide to spend the prime years of his career as an athlete and icon.
Greenberg, whose Allen & Co. brokers the biggest sports deals, worked with Gilbert on his attempted acquisition of Rawlings in the early 2000s, advised him on his attempt to buy the Milwaukee Brewers from the Selig family and finally helped him close the deal to purchase the Cavs. When James' agent, Leon Rose, had his practice bought by Creative Artists Agency -- which now represents the top three NBA free agents, James, Dwyane Wade and Chris Bosh -- Greenberg acted as an informal advisor to Maverick Carter, the CEO of James' marketing company, LRMR Marketing.
Greenberg knows Gilbert well, and also has experience with other NBA owners involved in the chase for LeBron -- namely Bulls chairman Jerry Reinsdorf and Madison Square Garden chairman James Dolan. (He calls Reinsdorf a "friend," but declined to comment on Dolan because he has been on opposing sides of past business dealings with him.) But he also has come to know LeBron and what makes him tick. Whereas most NBA players think Allen & Co. is another name for the Celtics' Big Three, when Greenberg first met LeBron, he was astonished that the budding superstar associated the name with the firm's annual conference for titans of industry in Sun Valley, Idaho, and wanted to attend.
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All of this has helped him form an opinion about what James will do -- an opinion more than worthy of inclusion in the vuvuzela-like drone of speculation that currently has America covering its collective ears.
"It's sort of like [Derek] Jeter," Greenberg said. "When his contract comes up, people don't say, 'Gee, I wonder if Derek is going to go play for the Giants in San Francisco.' He's so intertwined with the fabric of those pinstripes, and has been for so long with such success, and has been so comfortable in that environment. You used to be able to do it more, but [Cal] Ripken has done it. Jeter has done it. ... Despite all the craziness, I suspect Kobe [Bryant] is going to be a Laker for life. Those are few and far between in sports, but when you look back, those tend to be the players that have the greatest impact on the game.
"What's really extraordinary about LeBron's situation is, it's actually his hometown -- not just the team that happened to draft him -- and it happens to be not one of the top five markets," Greenberg said. "I kind of liken it to Warren Buffett. If Buffett lived in New York or the Greenwich, Conn., suburbs or San Francisco or Chicago, I actually think some of the mystique of being the Oracle of Omaha might have been diminished. The fact that he's lived in the same house in Omaha and it is his hometown tends to lend to the legend. So if you can do it in Cleveland or Chicago as opposed to New York or L.A., that only adds to it."
It is no secret, of course, that Buffett has become one of James' most influential mentors. So while I believe James could wield far more influence on the NBA -- and enhance his goal of becoming a billionaire and international icon -- by moving his one-man corporation to a major market, Greenberg is on the other side of the argument. All you have to do when deciding how much weight to give his opinion is look at his track record. He's usually on the right side of the biggest sports deals, and has experience with both parties who will be making (or not making) this one.
"Dan is the ultimate entrepreneur and the ultimate people person," Greenberg said. "If you look at any of his organizations, starting with Quicken Loans, there've been a couple of keys to his success. One is his sort of vision and leadership, but the other is his ability to attract, maintain and incentivize key executives over long periods of time."
Now, Gilbert chases the most important executive of his career.
"I imagine that Dan would want to have a multi-decade relationship with LeBron James," Greenberg said. "That's how he's thinking, and that will go for as long as Dan owns that franchise. That's going to be his approach. I know it's been his approach the last five years."
How does he do it?
"That is part of Dan's secret sauce," Greenberg said. "From a long time hanging around the sports industry, I've seen all kinds of owners; the good, bad and ugly, the smart and the not so smart. And over a period of time, the quality of ownership does tend to affect the way an organization thinks, acts and performs on the field or on the court. Dan is one of those guys. He's a winner, a winner in life, a winner in business, and he's going to be a winner in the basketball business, as he has been."
That's where we are, 36 hours from the biggest transaction of Gilbert's career. Greenberg said that if you asked 100 people to tell you the first thing that comes to mind when you say, "Cleveland," 50 of them would say LeBron James. If LeBron leaves, and you asked 100 people to tell you what comes to mind when you say, "Dan Gilbert," he would be the guy who let LeBron James get away.
We are days away, maybe even hours, from a transaction that will define them both. Greenberg, sports' biggest deal maker, isn't in a position to bet against either one.




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