On Monday, Brandon Lincoln Woodard, a 31-year-old law student and apparent bon vivant, was killed with a single shot to the back of the head during an alleged broad-daylight execution on the streets of midtown Manhattan. The suspects — one gunman and one getaway driver — allegedly waited for Woodard near Columbus Circle, shot the victim as he walked by, and then absconded into the streets in a rented Lincoln MKZ. 

The motive of this crime is still quite murky, but really, the whole scheme is baffling. How did the killers know they wouldn't get stuck in traffic? Anyone who has ever driven in Manhattan knows that the specter of gridlock is omnipresent. How did the suspected murderers know they wouldn't peel off only to find themselves immediately stuck behind a tangled, honking mass of taxicabs? Also, aren't there, uh, less conspicuous ways to off a guy than by shooting him in the middle of the day in one of the busiest places in America? Were these the dumbest criminals in New York — or incredibly savvy killers? "You can characterize it as either being brazen or foolhardy," says police commissioner Ray Kelly.

Well... which is it?

Patrick Estebe, president of high-end security firm AffairAction, hypothesizes that when criminals attempt escapes in crowded streets, they could be relying on expertise. "They may have had an excellent driver," he told me. "Maybe he can do better in traffic than the guy following him can. If that's your card, then you play it. Like Ryan Gosling, in that movie [Drive]. You can assume that it's nuts [to flee into traffic], but then again, they got away, so how nuts is it really?"

David Katz, a former DEA agent who now runs Global Security Group in New York, isn't about to give the bad guys quite so much credit. "It is ballsy," he told me, "I'll give them that. But one bad turn, one UPS truck parked in the wrong spot, and you're stuck. To me it seems like a boneheaded thing to do." He went on: "Professionals make sure they can control their environment, and there is zero way to control midtown Manhattan. Can you ever be sure you're going to get an open road there? No. Sounds like those guys watched a little too much TV."

And what about all the other problems with a daylight shooting in the middle of a crowded city? There are potentially hundreds of witnesses, not to mention security cameras all over the place. Estebe notes that such attention-grabbing hits are often not simply about murder — they're also about sending a message. "Killing someone is easy," he says. "You wait until it's dark, you make the kill, and nobody knows what happened — simple. But a bold assassination is a different thing. And it is much more scary. Killing the guy is only half the job. Scaring the next guy, that's the other half of it."

Katz disagrees. "I see it in the news like 'Professional hit! Professional hit!' but truth is that was as unprofessional a hit as it gets. No real pro would risk that kind of exposure — the traffic, the cameras, the witnesses, not to mention the place is crawling with cops, especially during the holidays!" He concluded ominously: "A professional wouldn't need to send a message by hitting someone in broad daylight. When the guy's dead, he's dead. And the other people involved will generally find out about it. With real pros you might find two things: A body, and maybe a hole in the head."