By Sam Amick
August 15, 2012

With a few twists of fate, Rob Hennigan -- aka the mystery man who traded Dwight Howard -- may have been the one judging as opposed to being judged last Friday.

Before the 30-year-old became the Magic general manager in June, and before he sent Howard to the Lakers in a deal that had some critics wondering aloud if Hennigan was not only the youngest executive of his kind in the NBA but also the worst, Hennigan was on his way to joining the much safer world of punditry. Two post-college job offers in the media industry were the latest products of his hardworking ways, the continuation of a successful run in which Hennigan became the all-time leading scorer at Emerson College in Boston and an Academic All-American.

But the internship with the San Antonio Spurs was just too good to be true, too paved with promise to pass up in favor of being the sports director of a television station in Fairbanks, Ala., or a sports reporter at another in Joplin, Miss. Sure, he had chosen Emerson in large part because of the school's renowned communications program, accepting the invite from coach Hank Smith not long after winning a Division I state title at St. John's High School in Shrewsbury, Mass. But because this was the Spurs and because of who was offering the job, Hennigan ended his pursuit of a journalism career and began his lane change into the NBA executive fast track.

Thunder general manager Sam Presti, a former Emerson star himself who had been granted the very same internship en route to his then-job as San Antonio's assistant GM, took Smith's spirited recommendation of Hennigan to heart and offered him the job. Presti had missed playing with Hennigan by a year at the Division III program, but his old coach was quick to tell him how well they would have worked together, how smart and diligent and efficient Hennigan was and how eerily similar the two of them were.

Eight years later, Hennigan -- who is just one year older than Presti was when he became a whiz-kid GM and two years older than standard-bearer Theo Epstein of the Boston Red Sox at the time of his ascent in Major League Baseball -- would leave his post as Thunder assistant general manager to execute the messiest divorce in all of pro sports between Howard and the Magic.

It was his union with and similarities to Presti, though, that had largely defined him. The promotions came quickly, from intern to basketball operations assistant and director of basketball operations in San Antonio to rejoining Presti as the director of college personnel in Oklahoma City when the team was transitioning from Seattle in 2008.

A Presti clone, some said, was being groomed. And considering Presti's impressive ability to build the Thunder into a championship contender so soon after taking over in 2007 when the franchise was in the midst of four woeful seasons, it was about as good as NBA labels get.

"I see a lot of similarities, and I always have," said Smith, who remains a friend and mentor to both men. "They're both smart guys, both extremely hardworking guys, guys who will never speak until they've thought out what they're going to say and won't make decisions until they've weighed all their options."

Hennigan, who is widely known as the humble sort and only agreed to be interviewed for this story after extensive prodding, spent more than seven weeks weighing his options with Howard after he was hired. He didn't do it alone, though, as he had continued the Presti parallel by hiring Pistons vice president of basketball operations Scott Perry as Orlando's VP and assistant GM. Before joining the Pistons in 2008, Perry was Presti's right-hand man in Seattle during his debut season with the Sonics. Hennigan also hired Bulls director of college scouting Matt Lloyd as assistant general manager, and on July 28 made 37-year-old Spurs assistant Jacque Vaughn the Magic's coach.

The group worked closely with recently promoted CEO Alex Martins in the Howard process. Martins, who picked Hennigan over far more experienced finalists in Dennis Lindsey (a former Spurs assistant GM who was recently hired as Utah's GM) and former Hornets GM Jeff Bower, reported to the DeVos family that has owned the Magic since 1991.

The Magic decision makers ended up trading Howard and three other players in a four-team deal with the Lakers, Nuggets and 76ers that brought to Orlando guard Arron Afflalo; forwards Al Harrington, Moe Harkless, Josh McRoberts and Christian Eyenga; center Nikola Vucevic; three first-round picks (a lottery-protected selection from the Sixers in 2015, the lower of Denver's two first-rounders in 2014 and the Lakers' 2017 pick); and two second-round picks (from Denver in 2013 and a conditional pick from the Lakers in 2015). Orlando was roundly criticized for not getting enough for Howard and accused of bypassing potentially better deals with Brooklyn and Houston. But team officials insist that this was the best available trade for their long-term plan, their preferred package of players, picks and salary-cap relief that still allows them to create a team in their image as they build toward the key free-agency summer of 2014 (when they have just $29 million on the payroll).

Afflalo, 26, is the centerpiece of Orlando's haul of six players and five draft picks. The Magic view Afflalo as being well-deserving of the $30.4 million he's owed for the next four seasons because of his combination of two-way talent and intangibles.

"We love his mindset, love his toughness, love his penchant to compete every day," Hennigan said. "We really feel that he's someone who can set the tone for the organization and help set the tone for the culture and the kind of work ethic and mindset that we want the players to embody. I just really like his makeup."

Afflalo, the 27th pick by the Pistons in 2007, had crossed paths with Perry before, during his second season in Detroit. It's his experience before then, though, that the Magic are hoping to repeat.

In 2004, UCLA coach Ben Howland made Afflalo his first recruit and relied on him to set the tone for the turnaround that was to come. Howland's Bruins finished 11-17 the year before Afflalo arrived, but in the next three seasons with the guard they went 80-24 with one appearance in the national championship game and another in the Final Four. The Magic, in some ways, have hand-picked Afflalo to play the same role.

In Harkless, the 15th pick in the June draft by Philadelphia, the Magic see a young player with serious potential to be their small forward of the future. In Vucevic, they see a versatile, smart big man entering the second year of his rookie contract who was a spot starter and improving player for the Sixers last season. Altogether, the chance to obtain young players who fit their vision while also netting the three first-round picks and two second-rounders appealed most to the Magic.

Sources with knowledge of the talks said that wasn't the case with Brooklyn's most recent proposal. Before Brook Lopez's re-signing on July 11 ended the talks with the Nets because he could no longer be included in the deal, the Magic -- who had a chance to get four first-round picks (with Nets guard MarShon Brooks being traded to the Clippers, or some other third team, in exchange for one of the picks) -- had been against the idea of saddling their payroll with Lopez on a maximum contract (four years, $61 million) or, to a much lesser degree, power forward Kris Humphries on a deal that would guarantee him about $10 million next season. Most, if not all, of those picks would likely have all been late first-rounders based on any reasonable projections of the Nets' future (and that of the Clippers, if they had signed off on that deal).

The offerings from Houston, sources said, weren't as plentiful as previously believed either. In both the two-team talks with Houston and three-team discussions that involved the Lakers and would have sent center Andrew Bynum to the Rockets, sources said Houston was offering only two first-round picks. From Houston's perspective, however, the comparative value of the picks far outweighed anything available to the Magic elsewhere and it had been made clear that a third pick could be added "if it got the deal done."

One of the picks, which would have come via Toronto as part of Houston's recent trade of point guard Kyle Lowry, has protections that make it likely to land in the lottery. The other being offered, by way of Dallas, had an outside chance at becoming completely unprotected in 2018 if the Mavericks didn't finish the regular season in the league's top 10 in the five years prior.

Many assumed that the Rockets' three first-round picks from this year's draft -- guard Jeremy Lamb and forwards Royce White and Terrence Jones -- would be made available in a Howard deal. But sources close to the Magic said Lamb was the only such prospect offered, and that he was off the table by the time the talks involved the Lakers and Lamb had impressed at the Las Vegas summer league in July (he averaged 20 points in five games). Meanwhile, unwanted players like Gary Forbes, Jon Brockman and Marcus Morris were made available (along with shooting guard Kevin Martin, whose expiring $12.9 million contract was a must to make the money work).

On the Rockets' side, meanwhile, sources said the message had been sent that the Magic could have one or possibly two prospects from a pool that included Morris, Patrick Patterson, Lamb, Jones, White and Donatas Motiejunas. Houston offered significant salary-cap relief, but, as had been the case on the topic of young players, never in the form that the Magic wanted.

"I enjoyed working with Rob on a potential deal," Rockets general manager Daryl Morey told via text message. "He went with what was best for Orlando and over time people will see that he has made a good decision. He has a plan for Orlando and he has proved his ability to execute a plan to make franchises great from his time in San Antonio and Oklahoma City."

Hennigan wouldn't discuss the negotiations in any detail but made it clear he is content.

"What's available in theory and what's available in reality aren't necessarily the same," he said. "At the end of the day, we're happy with the net result of the trade considering the circumstances."

Critics decried the deal and lamented how the Lakers' acquisition of Howard was the NBA's latest case of the rich getting richer. Fans who may not have known Hennigan's name filled the airwaves with questions about what in the name of Superman was the Orlando general manager thinking? Hennigan, true to form, insists he wasn't fazed.

"It's somewhat similar to bench chatter in baseball, just a lot of noise floating around in a lot of different directions," said Hennigan, who was a shortstop ("good glove, [bad] bat") on his high school baseball team. "But really, what does it mean? I think if you can hit the mute button as much as possible and try to stay focused on making decisions that are rooted in principle, I think your chances of making a good decision increase exponentially.

"Our goals going in were to remain flexible, create a chance to have some long-term sustainability, and the avenue to that is a mixture of what we were able to get back."

As early-tenure deals go, trading Howard is as daunting as it could get for Hennigan -- like taking the driver's license test in your father's Porsche. He was a valued member of the Thunder's brain trust, but Presti and assistant general manager Troy Weaver (who was also a candidate for the Magic job) were typically the ones working the phones in the office while Hennigan's greatest impact came from scouring the globe to find new talent and innovative ideas to bring back to the group. Hennigan spent about 20 nights per month for nine months out of the year on the road scouting for Oklahoma City.

"When the DeVos family and Alex hired me, I was just really humbled and really excited," Hennigan said. "For a second, it really hit me how much work was ahead of me. It was a little overwhelming for like a day, and then I said to myself, 'Well, you signed up for it so you'd better get to work.' That's the approach I took.

"At Oklahoma City and San Antonio, I was really lucky to be privy to a lot of varied discussions and negotiations. And a lot of times, I was fortunate enough to have an active role in that process. I think those experiences and observations helped me quite a bit and provide the foundation of, 'OK, here's how to operate, here's how to conduct your business, here's how to establish an action plan from which to operate.' That just gave me a lot of confidence to pick up the phone and start doing what was best for the organization."

The relative anonymity of his past life was gone, replaced by a central role in a story that captivated the sports world and even spilled over into the pop culture realm. Among the many moments of Hennigan's unwanted overexposure? A parody video of his singing Carly Rae Jepsen's smash hit Call Me Maybe to Howard, and the panel of ESPN's Around the Hornriffing about Hennigan's name during commercial breaks just after he was hired. On the other side of the saga, Howard could be counted on to provide an update via TMZ every so often.

What little Hennigan saw of the circus was torture for a man who takes his humility seriously. Ask him about his past experiences or to explain how he won the job over candidates with longer résumés, and he'll tell you over and over again that he was "lucky." Ask him to talk about himself, and he'll cringe.

This is the guy who was known for not celebrating game-winning shots during his playing days, who once had an impressed friend send him a cell-phone picture of the banner inside the Emerson gym honoring his scoring achievements and responded with "Yeah, I was a little bit of a ball hog." So, yeah, he'd be just fine if the spotlight dimmed a bit and no one asked him to talk about himself.

Martins, however, can't say enough.

"Quite frankly, I think he's going to be a star," Martins told just days before the Howard deal. "As time goes on, I think he's got all the makings of being a great GM."

Martins felt good about the decision immediately. The Magic not only vetted Hennigan in all the traditional ways but also did extensive personality tests that Martins estimates were "probably as much or more than anybody has ever done" in the NBA. What they discovered was a man with experience well beyond his years, and with an even-keeled temperament that was precisely what they were looking for.

"He's unflappable, OK?" Martins said. "I was most impressed with him six or seven days into the job on draft night. Clearly you can understand what would happen in the dynamics of the league with a brand-new guy who just came on board who everyone says is young and some have identified as not as experienced as you would expect, so everyone's calling up and trying to take advantage of the guy.

"I was sitting right next to him, and I was so incredibly impressed by how unflappable he was. He wasn't going to get pushed around. To me, in that first week, that solidified and gave me the confidence that we made the right decision."

That Hennigan began to prove himself on draft night is appropriate, given Orlando's plan. The Magic, according to Martins, entered their general manager search with the memories of draft failures fresh in their minds and determined to find someone who could fix what was broken in their evaluation process. Then here came Hennigan, a wunderkind from the revered Spurs and Thunder programs that were so successful in building through the draft.

"He grew up in that tree in the very beginning of his career," Martins said. "He took that [experience] with Sam, and they were able to build their own culture with [Thunder owner] Clay [Bennett] in Oklahoma City. To me, that approach, that experience, was priceless.

"With all due respect to what we've achieved in the past -- because we have been pretty successful -- it was a lot more about the decision making from the gut, so to speak, as opposed to utilizing good information, good intelligence. That was one of the things that stood out in Rob's interview. We were really impressed by the network of intelligence that he's utilized in the past and would utilize with us moving forward in terms of making decisions."

Martins and the DeVos family decided that the Magic would no longer be known as a team that conducted far fewer draft workouts and player interviews than most, if not all, of their rivals. The Magic, they vowed, would join the modern era of player evaluation and team building. No more huge contracts for players who aren't truly difference makers. No more shortcuts in the process that may have, as they see it, cost them a chance to win it all with Howard and keep him around for the rest of his career. And certainly, no repeats of the Fran Vazquez situation.

Of the Magic's missteps, the one stuck in their craw is the selection of the Spanish big man with the 11th pick in 2005. A player who appeared to be a complementary frontcourt mate for a young Howard became the player who never showed up. Vazquez has remained in the Spanish ACB League since being drafted and re-signed there as recently as this summer when it seemed he may finally join Orlando.

Within the organization, Vazquez -- who was taken six spots ahead of Indiana's Danny Granger -- has become a reminder that knowledge on all fronts is power. With more intelligence, more relationship-building and extensive homework, the Magic might have known that Vazquez -- and others like him -- wasn't worth a hefty investment.

"There's a number of guys over the course of our history where we'll bring him into the organization, primarily through the draft, spend a couple years with him and then they'll move on," Martins said, citing point guard Chauncey Billups, a five-time All-Star who had a brief stay in Orlando in 1999-2000, and center Marcin Gortat, who spent his first three-plus seasons in Orlando before being traded to Phoenix and breaking out over the last two seasons.

"What I like about Rob's approach from the San Antonio system is, 'Make the right decision, develop your guys, keep them with you.' Sustainability over a long period of time."

It's fitting that Hennigan would wind up with the Spurs, for whom he worked from 2003-07. Hennigan's natural tendencies were only strengthened during his time in San Antonio, where it wasn't just the drafting of David Robinson and Tim Duncan that led to four championships since 1999. Spurs general manager R.C. Buford and coach Gregg Popovich have built one of the healthiest cultures in professional sports, a place where selflessness and a relentless work ethic are always expected, and those who were there say Hennigan blended right in. While his intern role at first included menial tasks like picking up players from the airport, it didn't take long before he was making his way up and leaving a lasting impact on San Antonio's highly regarded scouting system. As Buford remembers it, Hennigan was promoted for the first time after a year and became a part of the team's regular scouting schedule after his second year.

"He had a very mature understanding of what he knew and what he needed to know, and had a very calculated and mature approach to growing himself and helping us grow in areas that were new to us -- new to people who were scouting basketball," Buford said of Hennigan recently. "The data collection, the development of our internal information systems, were all a big part of Rob's contributions. At the same time, he was a diligent film watcher.

"And as he grew through the scouting role, I think he had a very confident approach to his evaluations and his ability to transfer those evaluations to discussions among our group, among our coaches. His opinions were well-grounded and well-researched, so he spoke confidently in a pretty intimidating atmosphere."

Hennigan did not have a single defining moment like Presti, who is credited with making an internal push to draft a French point guard named Tony Parker with the 28th pick in 2001. Hennigan's legacy in San Antonio was much more subtle.

"He was consistent," Presti said. "He had a really high work capacity. He was able to finish projects and round things out beyond what you might have initially asked for. He wasn't in a rush to impose himself on the entire decision-making process. He was really comfortable trying to support those decisions with his work. And over time, he organically built a level of respect among R.C. and [then-VP] Danny [Ferry] and myself through just consistency and willingness to do the dirty work."

The path alongside Presti continued in 2008, when Hennigan (along with his college-sweetheart wife, Marissa) left San Antonio to join a Thunder organization that was transitioning to Oklahoma City after the Seattle chapter ended with a 20-62 season. Weaver came that year as well after serving as Utah's director of player personnel.

Those were the golden days of Presti's ascent, with both the general manager and Weaver receiving well-deserved credit for drafting Russell Westbrook, Serge Ibaka and James Harden as part of the Thunder's methodical rise. Hennigan had a respected voice in his own right with the team -- "He had input along with the rest of the guys in our front office into each decision that we made," Presti said -- but he made his biggest mark by feeding and helping form the scouting department through countless trips around the globe.

"You could tell the guy, 'Hey, go to Moscow tomorrow, then jump over to Tel Aviv.' He wasn't afraid of any of that," said Trail Blazers assistant general manager Bill Branch, a former director of pro player personnel for the Thunder who worked two seasons with Hennigan. "He's the type of guy where if you dropped him off in some random country, he wouldn't panic and would find his way back. And he may make a few friends along the way.

"When you talk to him, you realize that he has an uncanny knack of getting a grasp of something very quickly. Whether that's IQ or just a great understanding of things, that's the one thing I really noticed about him. It's how quickly he's able to assimilate the information and come up with an answer."

The way his basketball mind is wired doesn't hurt, either, at a time when NBA teams are valuing player efficiency more than ever. As a 6-5 guard at Emerson, Hennigan once scored a career-high 47 points while having his hands on the ball for a combined three minutes during a game against Suffolk University.

"He very rarely put the ball to the floor," said Smith, his Emerson coach. "His big thing was reading screens, coming off curls, pull-up jump shots, threes in transition. He had maybe the most efficient game that I've witnessed. He was phenomenal. There were so many games where he'd have 29 points on 10 shots, 26 points on 11 shots. It was on and on. His efficiency was amazing."

The mentality, if not the jump shot, remains.

"I certainly think that as a player he was way ahead of his time, and today that's the way he thinks," Smith said. "You've got to incorporate different pieces within a team to be more efficient."

Which is Hennigan's charge now -- to spend the next few years using this flexibility wisely and efficiently as he puts those pieces in place in the post-Howard landscape. As Perry sees it, Hennigan has what it takes to quiet his critics in the end.

"He has displayed a calmness and a poise that people wouldn't normally associate with someone his age," said Perry, 48, before the Howard deal. "He understands the need to have a good balanced perspective with this whole thing, and I think that's important. He's demonstrated that.

"It's his attention to detail, the going the extra mile, doing a lot of homework, understanding how a team can evaluate players from all sides, understanding that there is a variety of factors that go into identifying players who will fit your culture. It's deep background, finding out who this person is and understanding that all those components -- weighted properly -- will help you pick the best people for your organization. It's not a total exact science, but Rob will be as informed as he can possibly be."

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