Not much has gone right for Dwight Howard since he first demanded to be traded by the Orlando Magic. When this process began, he was widely considered the best big man of his generation. Two years later, the endless speculation about his future has left his reputation in tatters. The scrutiny was his fault, but the devastating back injury that left him a shell of himself was not. Now, with the worst of his recovery behind him, the biggest decision of his career looms ahead. The contract Howard signs this summer will take him through the end of his prime years. This time, he has no one to blame but himself.

When he came to the Los Angeles Lakers, the drama was supposed to end. He would be the next in a long line of Lakers' big men, the centerpiece of a championship organization for the rest of his career. Instead, one by one, the stars he was supposed to play with began going down. Next season, Steve Nash will be 39, Kobe Bryant will be 35 and Pau Gasol will be 33. They’re unlikely to get healthier as they get older. To keep Dwight in town, the Lakers will have to sell him on a vision for 2014 and beyond. As a result, if championships are his goal, the Houston Rockets are the safer bet.

Of the teams lining up to make a run at Dwight this summer, Houston is the one who should scare the Lakers. The Dallas Mavericks and Atlanta Hawks have worked furiously to clear cap space, but in the process, they’ve left their teams without the pieces necessary to lure a star in the first place. The Mavericks had a 41-41 record this season and their best players are all over 34. The Hawks, in theory, could sign Howard and Chris Paul, but all signs point to Paul re-signing with the Clippers. There certainly wouldn’t be Cliff Paul ads all over TV if he was losing in the first round in Atlanta.

If Dwight goes to the Rockets, everything would already be in place. Rather than playing with aging stars at the tail end of their careers, he would be joining one of the youngest and most exciting cores in the NBA. Houston, meanwhile, is becoming a model organization. They have an aggressive front office who can find talent anywhere in the world and a coaching staff willing to think outside the box. On the court, they operate by many of the same principles used by Stan Van Gundy with the Magic, with an offense revolving around spacing the floor and moving the basketball.

Most importantly, they have James Harden. While many doubted whether he was a max player, he established himself as one of the NBA’s best this season. Still only 23, the bearded wonder averaged 26 points, six assists and five rebounds a game on 44/37/85 shooting. Harden is the rare young player who relies more on savvy and feel than pure athleticism; he should be a lock for the All-Star Game for the next decade. An unselfish superstar who enjoys giving up the basketball, Harden would be an ideal pick-and-roll partner for Dwight, getting him 3-5 easy baskets a game rolling to the rim.

The supporting cast is in place too. By the end of their first round series with the Thunder, the Rockets were starting Harden, Chandler Parsons, Patrick Beverley and Carlos Delfino around Omer Asik. Insert Dwight for Asik and that is a serious team. Delfino’s $3 million team option for next season would have to be declined to clear cap space, but Beverley and Parsons are both locked into outrageously team-friendly contracts until at least 2015. The Rockets' core would make Dwight’s life easier, not more difficult. After missing the second round for three straight seasons, there’s something to be said for that.

Only a few tweaks would be necessary to build an elite team. A power forward capable of defending on the low block and stretching the floor out the three-point line would be ideal, but a marginal defensive 4 with an 18-foot jumper would suffice. Then a 3-and-D wing, a backup big man and a second ball-handler to fill out the bench. It’s hard to say exactly how Omer Asik, Jeremy Lin, Greg Smith, Thomas Robinson, Terrence Jones, Donatas Motiejunas and Royce White would fit in with the new plan, but all have enough value on the trade market to be flipped for usable pieces.

And while Houston would be tinkering around the edges, the Lakers would be undergoing a wholesale renovation. How much can you count on Nash, given how fragile he has become? Can Kobe make it back from an Achilles injury at 100 percent? If he does lose a step, will anyone tell him he needs to become a secondary player? Does Mike D’Antoni have the backing of the organization in the event of a power struggle? For that matter, can D’Antoni even build an offense that incorporates Dwight and Pau’s talents? Why am I asking these questions like we don’t already know the answer to most of them?

With so many questions about their top players and absolutely no room to maneuver under the salary cap, the Lakers won’t be in a position to improve until 2014. At that point, Dwight and Nash would be the only significant contracts on the books and they would have the freedom to make any number of moves. But while Los Angeles is a proven attraction in the free agent market, there’s no way to know what players will be available after next season. A number of big names could conceivably be in play, but as Dwight knows full-well, a lot can change in that much time.

In essence, while Mitch Kupchak can talk to Dwight about the labor pains, Daryl Morey can show him the baby. As Mark Cuban found out last summer, free agents value certainty more than “financial flexibility”. It’s easy for a GM to say they will improve the team down the road; it’s much harder to actually do it. That’s why so many Team USA players let their contracts lapse in the summer of 2010. If they were all free at the same time, they could lock themselves in a good situation without needing a front office to do much heavy lifting. From the players perspective, 99 percent of them haven’t earned the benefit of the doubt.

Of course, there’s more to Dwight’s decision than just basketball. Houston is a big market, but it doesn’t have the glamour or the weather of Los Angeles. The Lakers can offer him a fifth year and an extra $30 million and they will always be the most attractive destination for any player looking to build his brand. However, winning is the only thing that will fix Dwight’s brand now. If he leaves, he’ll be blasted for being disloyal, but if he stays and the team doesn’t improve, the knives will really come out. Money is money, but Dwight’s going to have to take less to win anyway. That’s what everyone in Miami did.

If Jerry Buss and Phil Jackson were the ones making the pitch to stay, a rebuilding year would be easier to swallow. Morey and Kevin McHale, in contrast, can pitch never rebuilding again. As Dwight ages out of his prime, Harden will just be entering his. In 2020, when Dwight is 35, Harden will be 31; Rockets versus Thunder could be the Spurs versus Mavericks of this decade. The Lakers might be able to find a star in 2014 or 2015, but he’ll probably be closer to Dwight’s age, shortening the window to win significantly. Things might work out there, but after the last two years, can Dwight risk turning down a sure thing?