Posted: Tuesday May 17, 2011 11:04AM ; Updated: Wednesday May 18, 2011 12:02PM
Michael Rosenberg
Michael Rosenberg>INSIDE THE NBA

Cavs owner Gilbert willing to spend whatever it takes to win

Story Highlights

Dan Gilbert may be unconventional, but he's committed to winning

Gilbert was willing to spend nearly $30 million on two first-round draft picks

Gilbert, Cleveland caught huge break when they landed Nos. 1, 4 picks in Lottery

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Cleveland owner Dan Gilbert has pledged to do what it takes to turn the Cavs into a winner again.
Cleveland owner Dan Gilbert has pledged to do what it takes to turn the Cavs into a winner again.
The Plain Dealer /Landov

When last we left Dan Gilbert, he appeared to have lost his mind, along with the minds of anybody within three miles of him. LeBron James had left Gilbert's Cleveland Cavaliers for the Miami Heat -- I don't remember the details, but I vaguely recall the announcement being televised in some way -- and Gilbert was livid. He wrote one of the great letters in the history of sports, an angry screed that included this passage:

I want to make one statement to you tonight: "I personally guarantee that the Cleveland Cavaliers will win an NBA Championship before the self-titled former 'king' wins one."

You can take it to the bank.

The country laughed, because there is nothing we enjoy more than laughing at rich people who fall on their face. Its guilt-free laughter, a USDA-approved plate of schadenfreude.

Gilbert was not laughing. He was not joking. And look at him now.

Gilbert got lucky when his Cavs got the No. 1 and 4 picks in the Lottery on Tuesday night. But as we all know, luck is what happens when preparation meets opportunity in the safe-deposit section of a large bank. Gilbert went hard after his luck. He paid for it. And when you're a sports owner, paying for it and earning it are the same thing.

Dan Gilbert just executed one of the most financially aggressive strategies in recent sports history. Well get to how in a minute. First: why?

The self-titled King is in the Eastern Conference Finals while Gilbert is running one of the worst teams in sports. After LeBron left, the Cavs became something you don't see much in sports these days: lovable losers. They sold out games. They played hard. They shocked some of the best teams in the league, including the Heat. But mostly they lost, and losing is only lovable for a little while. I suspect Gilbert did not love it for even a day.

Now, back to that letter. Everybody thought Gilbert was insane. He is not. Gilbert might be wrong; I believe he will be wrong. I believe LeBron James will win a title with the Heat, though I'm skeptical it will be this year. (Also, it is possible, with Dwyane Wade turning 30 next January, that Wade's body will break down and this Heat group will never win a championship. But that is a separate discussion, and not a pleasant one. I hope Wade has a long career.)

Anyway, Gilbert may be wrong, but he is not crazy. He is determined. There is a difference. That last line -- "You can take it to the bank" -- is the one we need to take literally.

Dan Gilbert has put his money where his mouth is, in a way that is almost unprecedented in the NBA. At the trade deadline, the Cavs traded in-his-prime point guard Mo Williams for prime-rib-loving point guard Baron Davis, who hasn't tried in two years.

The Cavs must pay Davis roughly $29 million over the next two seasons. Williams gets $17 million. (Jamario Moon, who was included in the deal, has a team option of $3.2 million that the Clippers can decline if they choose.) The Cavs also got the Clippers' 2011 first-round pick in the trade.

This means Dan Gilbert spent $12 million for one first-round pick.

He was not done. The Cavs tried to acquire Rip Hamilton from the Pistons for a 2012 first-round pick. Hamilton had fallen so far out of favor with the Pistons that his line in the box score read "DNP-%&!#$!" Hamilton is owed a maximum of $25 million over the next two years. Gilbert didn't care. Hamilton had zero interest in playing for the Cavs. Gilbert didn't care about that either.

Gilbert was willing to either let Hamilton play for the full $25 million (if Rip changed his mind about Cleveland) or buy him out, presumably for at least $15 million. Hamilton wouldn't take a buyout, out of pride (which was dumb, since he would be playing for the Bulls right now, and would have made most of his money), so the trade got nixed.

Add this up: $12 million in the Davis trade, plus at least $15 million (I suspect quite a bit more) for the Pistons' pick. Gilbert was ready to fork over around $30 million for two first-round picks -- neither of which is likely to be in the top three in the draft.

The Clippers' pick only had a 2.8 percent chance of moving up to No. 1 this year. Gilbert wanted that 2.8 percent, wanted it desperately. He wants as many chips on his side of the table as he can find. And his long shot came in: the Clips pick is the one that jumped to No. 1

The Pistons pick next year would have been protected; if it was at the top of the draft, the Pistons would have kept it. (This is because the Pistons, unlike the Clippers, are not stupid.) Still, Gilbert was willing to pay at least $15 million to grab that Pistons pick, and probably more.

Think about this: ALMOST THIRTY MILLION DOLLARS. This is astounding. In 2009, the Lakers sold the No. 29 overall pick for $3 million. Kobe Bryant, the highest-paid player in the league this year, made $24.8 million. LeBron James and Dwyane Wade combined make $28.5 million. The Sacramento Kings' entire team only made $44 million.

Yet Gilbert was willing to spend some-$30 million for two first-round picks. And that is before he actually paid the guys that the Cavs picked.

I think it is safe to say that when the NBA locks out its players this summer, Gilbert will not be the one crying poverty.

Even if Dirk Nowitzki scores 65 points in a playoff game or Taj Gibson jumps 20 feet in the air, this may be the most incredible number of the NBA season: nearly $30 million for two first-round picks.

This tells you everything you need to know about Dan Gilbert. That letter last summer may have made him a punch line nationally. But he meant every word of it. We saw it as a rant, but I think he saw it as a plan.

The Gilbert who wrote that screed last summer is the same Gilbert who built Quicken Loans into a lending giant and the same one who is running the Cavaliers today. The man is manic about winning.

All owners say they want to win. Nobody ever buys a team and says "Hello, everybody! I am totally going to shed salary as soon as people renew their season-tickets. Also, I'm putting my two sons and all three of my mistresses on the team payroll. Now, what city do we play in?" No, they say they want to win. But once they take control, a lot of owners go back to being businessmen and worry mostly about making a profit. They're entitled to do that, but it's not much fun for fans.

Well, Dan Gilbert really, really wants to win. He has made plenty of mistakes in Cleveland, but he made almost all of them because he was trying to win.

I don't know if Gilbert will turn the Cavs into a contender. A lot goes into that, and the Cavs have an unproven management team. But it is not wise to bet against a man who is this hungry. Last summer, Gilbert sounded like he was whining because somebody took his ball away. That ball is back in the Cavs' hands now -- back in the hands of point guard Kyrie Irving, a future All-Star point guard, the sure No. 1 pick in the draft. Cavs fans now have a player they can believe in again. And they have him because their owner is as desperate to win as they are.
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