Written by Gary Benz

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Maybe once a gambler, always a gambler.

When Cleveland Cavaliers owner Dan Gilbert was pushing hard last fall to get casino gambling legalized in Ohio, opponents tried to sully his reputation by bringing up a decades old arrest he had for running an illegal bookmaking operation while in college at Michigan State in 1981. That Gilbert had a gambling streak in him was hardly a revelation given the arc of his career. That Gilbert has now doubled down on the future of his franchise, however, is.

Entering into a summer where stability and direction would seem to have been paramount, Gilbert instead has deliberately created enough turbulence that the future of his franchise now hangs in the balance. If he's successful, then this will serve as an object lesson in how sometimes the only way to win big is to gamble big. If he fails, the franchise and the city he's so heavily invested in are headed for some strong headwinds.

Either way, it's funny what a lousy game or two at the wrong moment can do to change the course of history.

Heading into this season's NBA playoffs, the Cavs were the prohibitive favorite to win it all. The trio of Gilbert, Danny Ferry and Mike Brown (with help from a boatload of able assistants) had seemingly put every piece in place and had them all pointed in the same championship direction.

But another playoff failure, the first one directly attributable to some rather puzzling and indifferent play from LeBron James, suddenly has the franchise looking as if the ghost of Ted Stepien is now in charge.

The first casualty of the shake-up was Mike Brown. Gilbert has owned up to making the decision himself after some healthy internal debate. Exactly why he made that decision hasn't ever been made completely clear but suffice it to say that Gilbert became convinced that if Brown couldn't get a team with James to the promised land he certainly couldn't accomplish that task without him, should that come to pass.

Fair enough.

Now comes the departure of general manager Danny Ferry, his resignation an almost certain by-product of the decision to dump Brown. That's a bit more puzzling.

There were times a few seasons ago when Ferry seemed unable to make a decision on how to improve this roster. There were also times when Ferry came out of that funk when his changes, particularly those made late in the season, were almost too bold to be absorbed quickly. But give Ferry his due. He worked hard to surround James with championship-caliber talent and nearly succeeded.

The Cavs didn't necessarily lack the talent to be NBA champs but they certainly lacked that je ne sais quoi to push them over the top. That's what appeared to eat away at Gilbert as he pondered the future of his investment over that agonizing two weeks following the Cavs' meltdown against the Boston Celtics.

As bold moves go in Cleveland sports, this is among the boldest. This isn't Randy Lerner bringing in yet another regime to try their luck with the Browns. And this certainly isn't the Dolans allowing Mark Shapiro to fire Eric Wedge so that he could eventually bring in Manny Acta to re-arrange the deck chairs on the Titanic.

To put this in historical perspective this is far closer to Jerry Jones, owner of the Dallas Cowboys, remaking his franchise by letting Jimmy Johnson go despite winning two Super Bowls. At the time Jones looked like a prototypical egotistical owner who felt he wasn't getting enough credit for what Johnson accomplished. Jones became convinced of his own greatness and thus decided to part ways with the architect of the Cowboys' resurgence.

It worked, but for only a few years. Barry Switzer did win a Super Bowl with most of Johnson's players but after that Switzer was soon gone and the Cowboys are still trying to get back to where they once were, It's been 15 years and they're still trying.

Gilbert isn't really another Jones but the fact that the two are now part of the same conversation isn't particularly flattering to Gilbert. At the moment he looks like just another meddlesome owner who lacks the patience necessary to truly be a champ.

The question that will always nag at all of this, particularly if James does leave, is whether Gilbert looked too deep for answers that already were floating to the top. It's possible, for example, that the Cavs failures had little if anything to do with Brown and Ferry and were actually the result of a distracted James succumbing to pressure like he never had before.

James purposely put himself on a path where this would be the summer of James no matter the outcome of the NBA Finals. James is the face of the league and every step he takes, every move he makes someone is watching him. Winning it all and then becoming the most important free agent of all time was the scenario he laid out for himself. Maybe it was just the enormity of this self-inflicted journey that got to James at exactly the wrong time and not Brown's puzzling playoff rotations.

From the sounds of James these days it doesn't seem like he's done much soul-searching for his playoff failures as he focuses instead on summits and sneakers and changing the face of the NBA by treating himself and his fellow free agents like chess pieces on one giant board. The soul-searching instead has been reserved for Gilbert and he's certainly gone all in on this one.

Taking gambles like this are always a matter of timing. It's one thing to dump a coach and a general manager but a wholly other thing to dump them just as you're trying to convince someone like James or even a free agent in the tier below that this is the place to play.

None of us have ever been in a position like James, Dwayne Wade or Chris Bosh and never will be so to truly understand what it takes to keep or get players like that within the tent is always going to be a guessing game. But anyone whose stated goal is merely to win multiple championships is going to recognize that a key to that is stability.

Maybe Gilbert looks like a hero to them, someone willing to make the boldest of moves in order to get where he needs to do and thus the team's instability at the moment is understandable. Maybe though Gilbert looks a little unstable himself and richest crop of free agents in NBA history will take notice of that instead and take their skills elsewhere.

Gambles are risk and in terms of sports, this is about as big as it gets for a franchise. If Gilbert is worried, he isn't showing it, which is a good quality to have if you're gambling at that level. That doesn't mean, though, that a whole bunch of other folks, from mere fans to businesses that depend heavily on a Cavs crowd 50 some nights a year in Cleveland, aren't. Gilbert is playing with their chips as well.

Gilbert said last fall that he really doesn't gamble in the traditional sense much anymore but when he does it's usually at craps. That seems appropriate. He certainly has the dice in his hands and is betting that he's about to roll a 7 or an 11. But in Cleveland, where the dice never seem to stay hot, we're used to that roll coming up snake eyes and it's those odds that Gilbert ultimately will have to overcome if the fans are to remain convinced that he's really the person who should be making these decisions in the first place.