It’s Monterey Car Week, where some of the most expensive and exclusive cars ever made are displayed and auctioned off. It’s the perfect event to see automotive legends—and it’s practically begging for a heist. Here’s how you theoretically could pull it off.

[Editor’s note: Obviously, we don’t condone or encourage illicit activities, like stealing, pirating and heisting. This is purely for shits and giggles. The organizers of the Pebble Beach Concours didn’t respond to multiple requests for comment. We can’t fathom why.]

I suppose the very best thing you could say about Monterey Car Week is that it’s the one time a year where everything that’s worth stealing is gathered on one peninsula that’s about 30 square miles big. You have your Ferraris. You have your Bugattis.

You have assorted other cars so expensive you didn’t even realize they were cars. Looking for a Siata and a Cisitalia rubbing shoulders? Look for them at Pebble.

This proximity cuts out a lot of the work for you, our imagined thief. But that everything is right up against the ocean makes it all feel like a naturally fenced-in area. A getaway might seem impossible. Do not despair. There are some challenges, but they also make a few different types of getaway methods feasible.

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The Package(s)

The first question to address is: What are you trying to get away with? You could pinch a couple dozen low-value cars to keep things under the radar, but then you run into a space issue. For all of my effort, I’d go in for the most bang-for-your-buck cars. Like vintage Ferraris and Porsches. Like a Ferrari 250 GTO that’s worth over $40 million. That’s the good shit. Stealing just one of those is like stealing 20 cheapo Bugatti Chirons. You don’t want to waste your time with peasant cars like that.

Photo: Ken Saito/Jalopnik

Now, you’ll also want to hone in on which event you’ll be targeting. All week long, the whole peninsula is inundated with multi-million dollar cars, parked up and down the main street of town. Presented across the sun-kissed lawns of Monterey. Rolled before flocks of Instagram watch influencers during various auctions.

To gather some intel, I reached out to an an expert in collecting and curating rare and valuable vehicles, who I won’t name here, for some information regarding transporting and displaying expensive cars.

Sportingly, they played along.

They didn’t go into extreme details, but they did reveal that most of the people who participate in the Concours are decently trusting folk. BIG MISTAKE. Don’t trust anyone in this world, not even the person you fall asleep next to at night.

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A thief might have a chance at getting the cars when they’re warehoused before the week kicks off, my source did point out, but the problem there is that you’d run the risk of dealing with private security.

A greater weak link in the chain of security happens at the event itself, when the cars are parked near the lawn the evening before an event. During those crucial hours, they are left unattended and watched over by temporary security guards, according to the source.

I reached out to a second unnamed person, who has worked the event after-hours in the past. They confirmed (after a laugh) that the cars are left out in the open during the night. Only a security guard or two watches over them. (Unfortunately, we were unable to confirm with event organizers the true number of guards patrolling on night duty. Nor were we able to confirm marine police presence. Look, if it were too easy, then everyone would be pulling off this job.)

The main thing to be aware of, our second source noted, is that the cars get car covers to protect them from any rain at night or dew in the morning. Not an issue at all.

That settles it, then. Night: That’s your window.

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By night, visibility has decreased significantly and the general public isn’t allowed in the golf course anymore. The few remaining security guards are easily taken out with tranquilizer blow darts. After that, you need to move fast, as there’s no telling what kind of attention their lack of response will bring.

Here’s your map, provided by the Pebble Beach Concours itself. Stuff like the Ferraris are kept near the first fairway, a little ways inland. It’s not that far. Sunday’s event is spread out across the finely mowed grass of Concours Field, backed by the ocean. We’ll get to that later.

Screenshot: Pebble Beach Concours

You can see there’s a rocky bluff that cuts down to the water, but that’s it. There’s really only one road in or out of the course, which rules out an immediate land getaway. Keep those roads in mind, though.

Scenario 1: Operation Aqua

The beauty of waterfront property is that it provides a distinct getaway opportunity. Plus, when you steal a car, people will assume you’ve driven off with it. You, a brain genius, won’t make that mistake.

This is what you’ll need:

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  • A barge that fits four or five cars (or however many you’ve got your eye on)
  • Crew for the barge
  • A small, inflatable motorized raft
  • A mobile dock system that extends from the bluff down to the barge
  • Six loaders armed with four jacks and dollies
  • Three covered car transport trucks with drivers; one empty, two filled with regular cars
  • Black tarps for the cars

Position two of the car transport trucks near the golf course on the well-known 17 Mile Drive. Have the third and empty one waiting for you at nearby Monastery Beach, about five miles south.

Image: Google Maps

Approach the course from Carmel Bay and dispatch the loaders on the separate, smaller raft so they can get ashore. Once they’re off the barge, position the mobile dock on the edge of the bluff.

Illustration: Jason Torchinsky/Jalopnik

The land team, having already been briefed on the location of the targets, locates them on the grass. First, they jack up the cars and slide the dollies beneath the wheels.

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You could hotwire the cars and drive them where they need to go, but these are vintage automobiles, both loud and temperamental. Reduce your risk and get dollies.

Then, as a team, you’ll push your first car toward the bluff and onto the mobile dock, where the car is locked in securely and and slides down onto the barge waiting below (the dock is surfaced in a kind of high-friction material to slow the cars down). Depending on the distance between the cars and bluff, you might need to push them a bit further than is comfortable. But if you aren’t strong enough to move the cars over that distance, well, you’ll have plenty of time to get buff in prison.

Repeat this as many times as you have room for on the vessel. Cover the cars with the black tarp to minimize their silhouettes. Once the barge is full, retract the dock. The land team boards the raft again and splits up from the main boat to rendezvous at another predetermined location.

Now it’s time for the getaway.

Hopefully you’ve gotten this far without attracting too much attention. Luckily for you, most of Pebble Beach has been drunk since about 11:30 in the morning off of free Grand Marnier at the McLaren tent and hasn’t heard much of anything for a while now. Also, the golf course isn’t exactly right by anything, so nobody’s going to hear a lot other than the surf.

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But if you have been detected by someone in their intermediary day-drunk-to-night-hangover phase, that’s why you have the first two trucks as decoys. One heads north, one heads east.

These trucks will be filled with private cars, yes, but private cars from people who have already paid to ship their cars independently of Monterey Car Week. The police will be looking for the cars you’ve just stolen on the roads or in trailers, so give them something to chase.

Meanwhile, the barge with the cars has coasted south and touched down at Monastery Beach, where the empty transport truck is waiting. Load the cars into that and head for the nearest highway. Where you go from there, and what you choose to do with your newly acquired cars, is up to you.

Scenario 2: Operation Caeli

Maybe Scenario 1 moves a little too slowly for you, maybe it requires a little too much manual labor. This is what you’ll need for Scenario 2:

  • Heavy-lift chopper
  • Barge with regular cars on it, covered with tarps
  • Crew of four
  • Steel cables
  • Some kind of attachable platform to secure beneath the car and to the cables
  • Cargo plane

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This plan is quick, dirty and loud.

Illustration: Jason Torchinsky/Jalopnik

Fly over the course and drop down your crew. You’ll already have four steel cables hanging from the belly of the chopper. If you’ve got a good Sikorsky, you’ll have a slung payload capacity of a solid 36,000 pounds. Keep it over the first car, while your crew slides the platform beneath the car’s rocker panels, secures its wheels to the platform so it won’t roll off and attaches it on the other side. Retract the cables by about 10 feet and do the same with the next few cars. Depending on how much cable you brought, you should have a stack of four or five cars when you’re finished. The crew rides with the final two cars.

This has to be done fast, do you understand me? Choppers make a lot of noise, noise that won’t be masked by the ocean. Fortunately, choppers are also fast themselves, as you aren’t hindered by traffic or tides. Meanwhile, now is the time to use the barge as a decoy to draw some of the heat off of the chopper.

Besides the very obvious Monterey Regional Airport, which is the first airport that law enforcement would check, you have five airports within about a 50-mile range from the golf course. Of these five, I’d lean toward the Clark Ranch Airport, as it appears to be the smallest. You’ll have your medium-sized cargo plane waiting there.

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Bribe the airline officials to look the other way while you unload the cars into the cargo plane while another team spray paints the chopper to another color and rewrites its serial number. Leave this in a hangar for a good, long while until the mess blows over. Fly the cargo plane to the undisclosed, secret location of your choosing.

Scenario 3: Operation Biohazard

Now, those two scenarios will work just fine for the other cars and events, sprawled wantonly on the fields into the night with utter misplaced trust in their surroundings.

But the main happening is the Concours d’Elegance on the 18th hole of the Pebble Beach golf course, right by the water. This is the Sunday-only judged event, the classy one. And for you, a classy criminal, this is the one to knock over.

For many of these events, the cars are driven into place in a kind of parade. It’s complete peacocking behavior and you must take advantage of it. Everyone lines up on either side of the road to watch them drive by. This is an excellent opportunity to scope out what’s there and pick your targets.

In the case of the Concours, you have what’s called Dawn Patrol, when all of the cars file onto the golf course before sunrise. Crowds are tight, and everyone is groggy, because it’s difficult for them to locate where the help is with the coffee. This makes hanging around unnoticed easy. You don’t even need to wear a disguise! Now, make note of where everything is parked.

How does one escape in broad daylight with millions of dollars’ worth of precious cars and surrounded by spectators, the wealthy and the social-climbing alike? Well, we tapped an expert. We called Dan Ott, a car thief who has stolen over 1,000 cars during his lifetime, according to a very excellent feature in the Cleveland Scene.

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Do not doubt Ott is legit. The Cleveland Scene noted that across 50 years, Ott has had two stints in federal prison, four in state prison and countless others in local jails.

Ott has jacked cars from shows and events before. In the past, they way he’d do it was he’d be there as they were setting up, watching how the cars were brought in. The cars weren’t driven most of the time, but instead were hauled in by enclosed trailers. Once the trailer delivered the car, they’d get parked somewhere off-site while the show was happening.

Ott would go and take down the information off of the truck that he’d need. On the last day of the show, generally what would happen was that the car would get loaded back on the trailer and the owner would leave it somewhere, like at the original staging area, and go to the clubhouse or restaurant or something afterwards. Ott would then take the whole truck or trailer, drive it somewhere secluded and load the goods onto his own trailer.

As for pulling off a heist at a place like Pebble, “it’s always possible,” he said. “Some are harder than others.”

He took a few days to think on it and called me back.

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Because there are no nighttime opportunities to rip off the Concours d’Elegance, Ott would get an enclosed car trailer (or two) and disguise it like a local hazmat truck. Hire some people to pose as security and create a disturbance with something big, like a smoke bomb. Get that security to tell everyone it’s a biohazard and evacuate the area.

A hazmat truck
Photo: Joe Loong (Flickr)

Your team, dressed as the authorities and rolling up in an authoritative truck, goes in to “investigate” the problem, while really loading the truck up with the cars. You might need to drop another smoke bomb to reduce public visibility. Once that’s done, simply roll out with the sirens on. Traffic will actually get out of the way for you.

“It would probably work,” Ott said confidently. “These days, everyone thinks everything is a terrorist.”

You might be wondering why anyone would bother stealing cars and not other types of precious commodities, like paintings. Cars are difficult to transport and they are usually pretty hard to disguise, especially the exceedingly rare ones.

The simple answer is: You’d be surprised how often this actually happens.

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James Dean’s “Little Bastard” Porsche 550 Spyder mysteriously vanished in 1960 when it was being transported from Miami to Los Angeles. And one of the Aston Martin DB5s that starred in Goldfinger was heisted in 1997 and hasn’t been seen since (although there have been rumors that it’s turned up somewhere in the Middle East). Hell, a Mercedes-Benz 300SL Gullwing was just stolen recently.

Tell you what, if you pull off a heist like this somehow and don’t go to prison, I don’t even want a cut of the money. Just tell me you got away with it because of these instructions.

That’s all the validation I need.