Orlando Magic general manager Rob Hennigan is just 30 years old. A former Division III basketball star at Emerson College who holds a degree in broadcast journalism, he is the youngest general manager in the NBA.
He spent four years with the San Antonio Spurs, the latter two of his tenure in the front office under the guidance of the much-heralded Spurs management.
After his time with the Spurs was through, Hennigan moved on to the Oklahoma City Thunder organization, where he spent time working with Sam Presti, the current general manager who has ties to Spurs general manager R.C. Buford.
The three make up a trinity of NBA front office royalty of sorts.
Buford made his career off of his immense talents as a scout. Presti followed suit by receiving a fair share of credit for convincing the Spurs to take Tony Parker in the 2001 NBA draft. Both Presti and Hennigan attended Emerson College—albeit at different times—and Hennigan became Presti's protege in Oklahoma City.
That all leads us to where we are now—the most dramatic, back and forth trade debacle perhaps since Bill Walton chose to sit out the 1978-79 season when his trade request was denied by the Portland Trail Blazers.
There's no reason to rehash the events of the last few months, but as of now, the Magic are mulling over the possibility of keeping Dwight Howard into the 2012-13 NBA season, according to ESPN's Chris Broussard.
That means the Los Angeles Lakers have a chance at missing out on one of the most coveted players of the summer.
This does not seem like a brilliant idea or intelligent business plan for Hennigan and the rest of the Orlando front office to be carrying out.
When Hennigan took the job, he said this (via ESPN per the AP):
Personally I look forward to sitting down with Dwight and sharing with him the vision and the direction we're going to go, and I look forward to listening to what his thought process is and where his head's at. At the end of the day, we'll take it from there.
No dice on that philosophy.
Less than a month after he was hired, Hennigan called the face of his franchise to plead his case and attempt to convince D12 to give the new personnel a shot. Howard would have none of that, and the saga pushed on (via ESPN's Ric Bucher).
Hennigan has exhausted all options, yet the Magic are talking about avoiding trades for the remainder of the offseason to hold out for a deal that better suits the organization.
There are too many risks to do that.
Howard is coming off of back surgery and there's no guarantee that he will play up to the high standards that he has set for himself in his first eight seasons. He could be a shell of his former self.
That's unlikely, but if he is, the Magic could find themselves without a suitor for their free agent to be, and might be left with nothing when Howard tests the free-agency market next offseason.
It makes sense that the organization is waiting for the right deal to come about, but the longer it waits, the more dangerous it becomes. There is a fine line between making a smart gamble and being reckless.
Hennigan also had this to say when the Magic hired him (via ESPN per the AP):
There's no question there's pressure. This is a pressure business and you've got to earn your keep, and nobody's going to try to do any favors for you. We're just going to keep our heads down and keep our sleeves rolled up and get to work.
Pressure. Could it be that Hennigan does not want to ship Howard for less than a perfect package because he doesn't want to be known as the general manager who helped to steer the entire organization into the ground?
Who is more at fault for the Dwightmare?
His lack of experience leading a front office would give plenty of reason to think so. That isn't to say that Hennigan isn't a good general manager and won't be for years to come, but he's treading on thin ice in Orlando already, something he knew when he took the job.