5 Roadblocks Preventing Dwight Howard Deals from Happening

Those who care and those who couldn't care less can agree about one thing when it comes to the Dwight Howard affair.

It's well-past time to get it over with.

According to Sports Illustrared's Sam Amick, the light at the end of the tunnel may be just around the corner:

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Before I duck out again, a Dwight Howard note: the Magic, I'm told, are hopeful that they can pull the trigger on a deal by early August (although I certainly couldn't tell you which one it might be).

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And yet, nothing has happened yet. Perhaps the last few days of radio silence are a sign that something is actually happening. Or, perhaps it's an indication that we remain just as far from a deal as we were at February's trade deadline.

With such a unanimous desire from all parties involved to move on, what could possibly be holding things up at this point? How could it be so hard to find a fair deal for a guy this good?

Of course, there's isn't just one answer. So, here are five of them.

Dwight Himself

Thanks to Dwight Howard's insistence that he be sent to the Brooklyn, the Orlando Magic had little-to-no leverage when actually negotiating with the Nets.

It's no surprise those talks broke down.

From Brooklyn's perspective, there was no reason to improve an offer when so few organizations were in a position to make competing offers. Because Howard wasn't willing to sign an extension with other clubs, the Nets became one of the only games in town.

That put them in an obvious position of strength at the bargaining table.

In order to compensate, Orlando general manager Rob Hennigan was forced into playing hardball and sending the message that he will hold out for the best deal. For now, then, that means no deal with the Nets.

However, that could change in January when recently re-signed Nets center Brook Lopez is once again eligible to be traded.

Dwight's Agent

Just when it was beginning to sound as if Dwight Howard were willing to sign an extension with the Los Angeles Lakers (in the event he was traded to the Lakers), agent Dan Fegan came out with this buzz kill of a statement (via ESPN's Ric Bucher):

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"Dwight's position has remained unchanged since the end of this past season," said Dan Fegan of LaGardere Unlimited. "He fully intends to explore free agency at the end of next season, regardless of what team trades for him, including Brooklyn."

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It's hard to understand the thought process here.

Howard insists upon being traded, but these kind of statements certainly don't help. Who wants to trade a grab-bag of premium assets for a guy who plans on exploring his free-agent options in a year's time?

Surely Fegan is up to something, probably something nefarious. How it will help his client get out of Orlando this summer is puzzling, though.

The Magic's Front Office

According to ESPN's Chris Broussard, the Orlando Magic have at least entertained the notion of waiting this whole saga out until February:

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An executive who has had discussions with the Magic regarding Howard said Orlando only will trade the star center in a deal that is great for the franchise. The executive said this has been Orlando's stance for the past "week or so."

Another executive who has talked with Orlando said he thinks the Magic may start the season with Howard and wait until the February trade deadline to move him.

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Broussard goes on to note that both sources acknowledged GM Rob Hennigan may simply be "posturing" in a bid to drive Howard's price up as his suitors become more desperate. Whatever the reason for Orlando's stance, the result has been a drawn-out process.

The Denver Nuggets pursued a similar strategy when taking calls for Carmelo Anthony, and it eventually paid off. The organization won a bounty of prized young talent from the New York Knicks that opened the door to an instantaneous rebuilding process.

Hennigan is no doubt hoping the Magic see similar results.

Complexity

Outside of the Brooklyn Nets, the Los Angeles Lakers have emerged as Dwight Howard's most widely discussed suitor.

The problem is that Orlando's front office isn't interested in taking on another big-name star who could dive into the free-agent market in a year's time. That rules out a direct swap for all-star center Andrew Bynum.

Instead, a third team would have to get involved, taking Bynum from the Lakers while sending the Magic a package of draft picks and young talent.

According to ESPN's Ric Bucher, the Houston Rockets and Cleveland Cavaliers are currently the most likely organizations to step in:

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The Lakers have engaged both the Rockets and Cavaliers in their attempt to land Howard, sources say, because those two teams have both interest in acquiring Bynum, and have the requisite salary-cap room to accept larger player salaries than they send out in a deal.

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While their involvement would clear one hurdle, finding an agreeable deal isn't automatic. 

The Magic have to like the offer they're presented, but so too would the Rockets or Cavaliers. Even if Orlando is satisfied with an arrangement, that doesn't mean a third party would be content with receiving Bynum alone.

Additionally, Houston and Cleveland would both have to seek a guarantee from Bynum that he would sign an extension, and that's hardly guaranteed. Without an assurance that Bynum would serve as more than a one-year rental, sending a package of prized possessions Orlando's way isn't especially palatable.

Dwight's Baggage

Teams may be enthralled with Dwight Howard's talent, but is this really the kind of guy around whom they want to build?

The Golden State Warriors were at one point among the teams ostensibly pursuing Howard, but owner Joe Lacob didn't respond with much interest when asked if the team was still holding out for the superstar's services (via NBA.com's Scott Howard-Cooper):

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“I doubt it,” Lacob told NBA.com at the gathering to introduce rookies Harrison Barnes, Festus Ezeli and Draymond Green. “I never say never. But we have somebody called Andrew Bogut. He is, in our opinion, one of the three best centers in the whole NBA, and in most people’s opinion. And he wants to be here and is a great fit. We think we have a really nice nucleus now going forward.”

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Notice those thinly veiled hints? Bogut "wants to be here and is a great fit." 

Those aren't the kind of sentiments most front offices would associate with Howard and for good reason. His public trade demands, flip-flopping positions and insistence upon getting his way in personnel (and perhaps coaching) decisions has to rub a lot of teams the wrong way.

If you're wondering why the market for his undeniable talent is as thin as it appears to be, just remember that teams are wising up and realizing that big names can be even bigger headaches.

Alternatively, a guy like Andrew Bogut would indeed be looking like a pretty safe Plan B.