It Might Seem Obvious What Happened to the United Healthcare CEO. Don’t Be So Sure.

A gunman dressed in dark clothing and wearing a mask across his lower face ambushed UnitedHealthcare CEO Brian Thompson on Wednesday morning in midtown Manhattan, where Thompson’s company was hosting a conference. New York City police said the shooting was a “targeted attack” and that the gunman remains at large, but few other details have been released. Surveillance video captured the moment the shooter calmly approached Thompson, pointed a pistol equipped with a silencer, fired multiple shots, and fled on an electric bike. Police are now combing through video footage to track him down, including at a nearby Starbucks the shooter visited.

Many who noted the details of the shooting had an immediate question: Is this what a professional hit looks like in real life? The NYPD has said nothing of the sort, but that didn’t stop speculation from running rampant online on Wednesday. Dennis Kenney, a professor at John Jay College of Criminal Justice with decades of expertise studying professional killers, had unique perspective on that. He’s spent time over the years dispelling myths about contract killings borne of movies and Law & Order episodes. He told me he found aspects of the attack peculiar, and agreed to talk to me while emphasizing that it’s too early to draw definitive conclusions about a crime for which very little information has been released. Our conversation has been condensed and edited.

Slate: What were your first impressions when you heard the details of the shooting Wednesday?

Dennis Kenney: The first thing that’s unusual is that the shooter appeared to have a silencer. They’re not impossible to get, but they’re not readily available. The second thing is that he appeared to have inside information on the victim’s location. He knew where to wait and when to wait. The fact that he used the silencer didn’t make sense to me at first, until I saw that the shooting took place at about 6:30 in the morning. Generally, if it was a mid-morning sort of thing, you’d want a gun that made a lot of noise to scare observers off. But obviously at that time, no one was around. It also suggested that the urgency of the shooting was important. CEOs of health care companies are just not that hard to find in isolated settings. So the fact that he chose to do it in midtown Manhattan was a little bit unique.

Police called it a “brazen targeted attack.” You have studied contract killing and so-called “hit men” and sought to dispel myths about these kinds of crimes. What do you think of speculation this was a hit?

I think it’s pretty unlikely. My understanding is the CEO was being investigated for insider trading and some other financial violation. The fact that he ran a health care company—they tend to leave a lot of angry people in their wake. So, it seemed to be someone who knew what they were doing, but the idea of a professional hitman, those are pretty few and far between. So I would think more likely it was somebody with a particular grudge that had access to inside information to know where to be and when to be there.

Do contract killings usually play out in such dramatic fashion?

A professional hitman would probably prefer to do something less public with limited exposure. Doing it the middle of midtown, there’s just too many things that can go wrong, so you probably prefer generally not to do it there. However, if it was time sensitive, then that would make a difference. There’s a range of hitmen, so it could be somebody that was hired, but it’s unlikely.

Is there any other reason you think it’s unlikely?

This obviously was not the target’s usual routine. A professional would generally try to catch him in his regular routine in a place where the exposure of the shooter is minimized so that the risk of being caught or observed is pretty low. Manhattan, particularly in midtown, you’ve got cameras everywhere. I understand that they’ve got some fairly decent shots of the guy’s face while he was in Starbucks or something like that nearby. The exposure was fairly high, and most professionals don’t like that amount of risk. Again, unless it was time-sensitive—there could be any number of reasons why it was important that it happened that day.

Has technology, such as surveillance cameras, changed the way professional killers operate?

That’s hard to know. Like most businesses, there’s a wide range of professionals. You’ve got some that are much lower end and others that are much more skilled and with better equipment. So, I would guess this person, if they’re hired, they would be relatively on the low end. The fact that appeared in the video that the guy’s gun might have jammed is also a little bit of a concern for a professional. You make sure your equipment works.

What kind of crime would a very public shooting like this generally suggest? Does it fit a particular profile?

The thing that that struck me was the fact that he knew where he was going to be and when he was going to be there. Generally, you get that information by observing the individual. You find their schedule and their routine, and then you intercept them somewhere along the line on their routine. This was obviously not a routine setting. So, he had to have some reason to believe that he was going to be coming out of that door at an approximate time to be able to lay and wait. Because it’s Manhattan, standing around waiting risks the likelihood of being challenged by a cop or security guard coming by, which suggests that he had reason to know when that the guy was going to be coming out. It suggests some sort of inside information.

What are some common misconceptions people have of contract killers? How do professionals differ from portrayals we often see in movies and TV?

I don’t watch that many of those kinds of movies. Most of the highly skilled folks that I’m aware of are assassins for government agencies or something such as that. But when you look at even those levels of individuals, there have been several attempted assassinations in D.C. of government officials by other government officials, and generally the only reason you know about them is that they were bungled. It’s a fairly difficult thing to do.

Do law enforcement agencies differentiate between a professional hit and other types of murders?

For the most part, the investigation is done the same way. If this was a professional, then it’s obviously someone who had reason to want him dead. Because he ran an insurance company, you would look at everything from individuals who have been turned down for insurance coverage and lost their spouse as a result of it. That would be one thing the police would look for. They’ll first look for the reason why he was killed. And once you come up with the reason, then it’s much easier to find the person responsible for it.