Charlie Gray was just 26 when he got his automotive heart broken. Though still young, Gray had a flawless reputation, the right connections—his father had owned a high-end car dealership in Beverly Hills for nearly two decades—and the money, $200,000 of which he’d already plunked down as a deposit. But Porsche was making precisely 918 of their new million-dollar, mid-engine 918 Spyder, and Gray was number 919 on the list. Porsche was prompt in returning his deposit, but for an aspiring predator in the supercar jungle, a six-figure refund is no consolation.

“It was really upsetting,” Gray said, as he sat in the Lodge at Pebble Beach awaiting the Concours d’Elegance, the premier event of Monterey Car Week. “A real bummed-out moment.” Gray, now 36, has one hand tucked inside the chest-baring jacket of his pleated, green Issey Miyake suit; the other is holding a complimentary glass of Billecart-Salmon Rosé he hopes will chase away his hangover. “I know, I know,” he says. “‘Poor little rich boy. You can’t have the Porsche you want.’”

A classic Bugatti on display at this year’s Monterey Car Week.

At the time, there was simply no way for Gray to get one. Successful buyers are prohibited from reselling their new 918s for two years after purchase—a common stipulation in the limited-edition market. When it comes to acquiring an ultra-rare model, simply being able to afford one is not enough.

Gray took some lessons from his loss. “I learned that whenever you see something you like, don’t stop. Do whatever it takes. Get it,” he says. “And I apply that philosophy all the time.” A couple of years ago, he started buying a new Cartier watch every month. “Most people thought I was fucking nuts. ‘Why all the Cartier?”’ He raises his wrist to display a Tank watch that looks like it was contorted by Salvador Dalí. “This,” he says. He looks over his glasses, as if to judge whether I comprehend its significance. “It’s the Cartier Crash. This is the unobtainable. You can’t buy it. You have to be selected.” To get one, Gray used his car-business logic: “The more you buy, the more you get.”

Don’t spill your drink: the lavish interior of a one-of-a-kind Bentley GT Speed.

These days, Gray is getting it and then some with a car collection that includes Ferraris, Porsches, and a growing number of personalized Bentleys he customizes through Bentley’s bespoke division, Mulliner Coachbuilt. (It takes its name from when the company built coaches for horse-drawn carriages.) Earlier this morning, Gray had a consultation with reps from the Mulliner team about his new … sorry, newest Bentley, a GT Speed that will include the company’s iconic workhorse W12 engine, an electronic anti-roll system, custom anodized air vents, and, crucially, the ability to play what the audiophile Gray calls “uncompressed audio.” Yes, the car has a CD player.

Rare under the hood, too: Bentley’s Speed Edition W12 engine will be used in only 120 cars.

Its interior will include a material no other Bentley GT Speed has: engine-turned aluminum in black. Gray had been dissatisfied with the usual interior options—in particular, the piano-black trim on the center console. (“It takes fingerprints,” he grouses. “It gets scratched. That’s not luxury.”) He told his contact at Bentley a story about a shade of black that Karl Lagerfeld had once extracted from watchmaker Audemars Piguet for his Royal Oak wristwatch. Some months later Bentley called their exacting young client with an invitation. Come to Crewe, they said, where Bentley’s 85-year-old English factory still operates. Gray recalls: “We get done with the tour and they say, ‘We have a present for you.’ They’d literally made custom black engine-turned aluminum for me. Wow!”

Handling

It’s Monterey Car Week and a wave of restless money has rolled onto the peninsula like a morning fog, as it has every year since the 1950s. It’s a week of parties clustered around roughly four days of events: the Quail, a $1,500 dollar ticket to view rare cars and new cars, with enough free oysters, caviar, and champagne to wash down the succession of presentations droning on in the background; a morning rally down the epic 17-Mile Drive; a Saturday of races at nearby Leguna Seca, all of which culminates in the main event, the Concours d’Elegance, a classic-car competition that includes a procession on the 18th hole of Pebble Beach.

The one-off, two-tone Bugatti Chiron Super Sport Golden Era.

What was once a fairly discreet weekend gathering of well-heeled gearheads has become slickly corporate, absurdly lavish and totally global. Monterey is not only where the car companies reveal new models but also where they host scores of their best customers and try to show them the Monterey Car Week experience of their lives while casually taking orders for their next small fortune’s worth of cars. This week, Bentley is treating 150 or so of their favorite clients to beach dinners and signature parties as well as a sumptuous reception perched over the 18th hole for the Concours itself. There’s not a better seat on the California coast.

Adrian Hallmark, Bentley’s impressively relaxed chairman and C.E.O., looks far beyond engine displacement and interior specs when it comes to connecting with customers. “We do things called Extraordinary Journeys. We organize tours where you can bring your own car, and we take you through the U.K. with Michelin-star experiences every night, and/or we go through Italy, and you go and watch Tosca at a private opera performance in the Coliseum. We did an ice drive in the Arctic Circle … all kinds of crazy stuff.” As he pauses, smiling to himself, the crinkles around his pale eyes deepen. “We’ve even had people buy Bentleys so they can come on the tour.” No one does that for a RAV4.

“What do people want?,” Hallmark asks. “They have more money than they can ever spend. What they want is fun. They want things to do. They want to be with nice people. They want to do things that they could imagine doing but can’t organize.” And they want cars they can’t find anywhere else. Which is why Bentley reached out to only 20 of their most loyal customers when they quietly introduced their Mulliner Coachbuilt line, in February of 2020.

Fog lights recommended: Bentley hosts driving tours through the U.K. for its favorite customers.

“Three years ago, we’d never sold a $2 million Bentley,” says Hallmark. “We didn’t know if it would work, so we went out to known collectors and gave them a proposition. We said, ‘Look, we’re going into coach-building. Here’s the first one we’re going to do. What do you think?’ At least 12 of them thought, Where’s my checkbook? The customers came from Hong Kong, Singapore, Continental Europe, the Middle East, and the U.S., and they became the first owners of the Bentley Batur, a $2 million marriage of performance and luxury.

“You can’t buy it. You have to be selected.”

There were no dealers involved in that first round, and no intermediaries, no matter how prestigious their clients. “If you can’t be bothered to buy a $2 million car yourself, we’re not interested in selling you a car,” Hallmark says, then clarifies. “We didn’t say it that way. We just acted that way.”

While these bespoke million-dollar cars are probably a loss leader—it’s vastly more profitable to sell half a million Ford F-150 pickups—a “halo car,” in the parlance of automotive marketing, is a powerful asset. And they’re a lot more fun than futuristic dream-mobiles that will never touch actual asphalt.

From soup to nuts and bolts: Bentley’s preferred clients are invited to dine in Bentley’s actual car factory in Crewe, U.K.

“A lot of companies build concept cars, and it costs them $5 to $10 million to create one,” says Hallmark. “They show it and they get feedback, but they never build it. We don’t do that. We just build these. And we get more publicity than we do out launching a regular car. And you get to own it and drive it and thrash it. And it’s got four-wheel drive and 700 horsepower, and you can drive it to the shops, or you can bring it to Pebble Beach and win a competition. And that’s what customers love.”

Maintenance

About 15 years ago, one of Carmel’s most coveted coves got a new neighbor: a modernist, multi-level, glass-and-stone stunner with a footbridge and a world-class view. According to Range Rover, the house is owned by “friends of the brand,” and for one week in August it is transformed into Range Rover House, a place for the car-maker to connect with customers and provide them with “a luxury experience brought to life, an oasis from Car Week where they can relax and enjoy.”

The Range Rover House hosts tequila tastings, spa rooms, sound baths—a sort-of immersive, meditative sonic experience—and master classes with guest lecturers from Hodinkee, Chase Private Banking, and Architectural Digest. Guests sip Chablis and scan the waters for the pair of sea lions who live in the cove below. This house, with its steady rotation of passed hors d’oeuvres, free-flowing liquor, and a jaw-dropping NorCal vista is an epic hang, or it would be if you could fill it with friends of your own. Instead, it’s filled with friends of Range Rover, who stroll from room to room luxuriating in their V.I.P. status.

Hands off: only seven of the the 2024 Range Rover Carmel were made.

But none of them are the real guest of honor here. That would be the creamy, dreamy, twin-turbo luxe mobile parked in the courtyard entrance. The 2024 Range Rover Carmel aspires to mirror the aching natural beauty of the town’s photogenic coastline, and, with mainly cosmetic upgrades from the Rover SV—watch-grade-ceramic wheel inserts, a two-tone-Borlino-leather interior, white ash-wood inserts in the door panels and steering wheel—it comes close. But who cares if you like the car? All seven of this year’s $370,000 Carmels were sold on the spot, and only to those who showed up at Range Rover House.

If, as Woody Allen said, “80 percent of success is showing up,” then in the quest for the rarest cars, that number might be closer to 100 percent. Parris Mullins, 41, is the motorsports director of O’Gara Coach, which is where you go to score a new Rolls, Pagani, or Bugatti in Los Angeles County. Mullins has been selling exotic cars since he was 18 years old, and he’s seen even great clients get denied.

“Someone comes to me and says, ‘I’ve got a McLaren GT, and I’m ready to go to the moon with one of their Ultimate Series cars,’ but those cars are invitation-only and you have to be an Ultimate Series owner to get an invitation.” Mullins says it’s “a chicken-and-egg situation.” He usually suggests the client buy a pre-owned Ultimate and then make damn sure McLaren updates their profile in their database, but there are no guarantees.

“If you can’t be bothered to buy a $2 million car yourself, we’re not interested in selling you a car.”

And while Mullins points out that every brand handles their rarities differently, creating relationships is always part of the equation. “Everyone has the same metrics”—by “metrics” he really means “money”—“so it’s important to show up. We get them in front of the C.E.O.’s, get them in front of the decision-makers, make sure they go to the private dinners. Show that you’re engaged with the brand. Make them feel good about you as a buyer. We create a road map for them to reach the status and visibility with the brand.”

Performance-car makers such as McLaren, Ferrari, and Lamborghini host race series, where competitive customers can put their new supercars through their paces, though not all of Mullins’s clients can participate. “A lot of C.E.O.’s of publicly traded companies are barred from any dangerous act. That stuff is real. They’re contractually barred from racing. I’ve got clients who can’t even ski anymore.” To accommodate them, all three brands offer a suite of driving activities from “wild to mild,” including non-competitive track days and gentler driving experiences, like the one McLaren hosted through the Japanese countryside. (Yes, they shipped the cars over.)

But the ways into the car manufacturers’ good books are many. Dr. David Warkentin, a chiropractor and medical entrepreneur, has found that his healing powers have accelerated him up Bentley’s wait-lists. On Saturday, before Bentley’s signature party, he adjusted Bentley America’s president, Christophe Georges. “He was limping the other day, so I’ve been adjusting his hip, and he is actually off his pain meds for the first time in a long time.”

Pretty as a picture: the Concours d’Elegance.

Lately, Warkentin is in acquisition mode. He’s building “an 8,200-square-foot, temperature-controlled garage with 18-foot ceilings and a turnaround” at his home in Scottsdale, Arizona, to house his two Porsches, two Ferraris, Aston Martin, Bentley, and 1962 Chevrolet Splitback Sting Ray, to say nothing of his six Lamborghinis. “When it’s done it’ll probably be about half filled out,” he says, “so once the garage is open, we’ll start filling it out more aggressively.”

He bought his first Lamborghini in 2017, when, he says, it was easier to buy whatever car you could afford. “The car companies didn’t really start with this exclusive, you-can’t-get-this kind of attitude until the last maybe three or four years.” In Warkentin’s view, there are now two types of buyers in the rare-car world. “There are the people that come in with their checkbook, and because they have a checkbook, they’re very arrogant about it. ‘Oh, here’s my money.’” Warkentin sees himself as the second type. “My attitude is, Thanks for allowing me to buy another car.”

Warkentin is bullish about the investment potential of all the aluminum alloys and carbon fiber in his new garage mahal, but his collection delivers on a deeper, more primitive level. I ask him if he likes having something that not everyone can have, no matter how rich they are. “It’s huge,” he says. “It’s a huge satisfaction.”

Responsiveness

While mass-market brands hand down their new model lines from on high, revealing their latest crossovers and monster trucks with a stilted Javits Center address by their top-ranking North American marketing executive, the smaller, nimbler makers of vastly more expensive cars can do it over a glass of champagne here at Pebble Beach, or a hot lap on the track, or on a scotch tour of Macallan.

So fluid is the relationship that some car-makers actually take cues from their best customers, allowing their expressed desires to inform future models. Aston Martin’s newest V12 coupe, the Valour, has something most million-dollar cars don’t: a stick shift. That’s because, over the years, Aston listened to their clients, enough of whom said, Wouldn’t it be cool to have a manual 12-cylinder?

Cars heading to Monterey Car Week cross the picturesque Bixby Bridge.

Aston is making only 110 Valours for the company’s 110th anniversary. Exactly which of their “apex customers” gets early word on which rare models might be coming down the line changes from car-maker to car-maker, and its particulars are a slippery hairpin turn where data meets relationships. Every company keeps close tabs on their customers with cross-referenced spreadsheets, detailed histories, and advanced C.R.M. (Customer Relationship Management) which is digital-marketing-speak for “Know your client.”

When Aston was ready to spread the word about the Valour, they literally just started spreading the word, often in person, best customers first. “Part of being in this upper echelon of clients is that they do find out before the public,” says Alex Long, Aston’s director of product and market strategy. “That’s their reward for being in the brand for so long.”

“My attitude is, Thanks for allowing me to buy another car.”

Long says Aston executives reached out to customers individually and informally, at least at first. “Can we have some time in April or May? I need to show you something … something cool the public hasn’t seen.” Meetings were arranged. Renderings were shown. Technical capabilities were revealed. Deposits were collected. And two or three years down the line, dream cars were delivered.

So, I press him, if someone who wasn’t a current Aston Martin customer but had somehow heard about the new Valour and just had to have one … someone like Warren Buffett, say, or George Clooney or Beyoncé …

“I think in those circumstances their fame is one dimension,” he explains delicately. “Obviously, their ability to buy is proven. So it’s about what kind of relationship that we think we can establish with them. You know, are you looking to build a collection? Will you come and join us at this event? Would you like to come and meet the C.E.O.?”

Even if you manage to land your dream car, your commitment to the car-maker has just begun. Ferrari and Porsche are notorious heartbreakers who demand fealty and loyalty from their prospective clients well after they leave the showroom.

The cardinal rule is: “Thou shalt not flip.” This means you have to wait a year or two before you sell your incredibly rare, bespoke, two-million-dollar car, even if—or, rather, especially if—it’s doubled in price and you could really use that extra $700,000. And the car companies are ruthless about exacting punishment from anyone who violates the rule.

Nice torque if you can get it: a Lotus Type 66 on display at the Quail, a Motorsport Gathering.

Steve Wynn, the hotelier and Las Vegas strongman, was once one of Ferrari’s indisputable top clients. He’d owned a dealership on the ground floor of his Wynn Las Vegas hotel since 2005. But when he flipped his months-old, $3 million 2014 LaFerrari—he said he simply didn’t like it —Ferrari was not pleased. Reps for the company asked him about the car during a routine annual meeting at his dealership. Words were exchanged, and the Ferrari reps were escorted off the premises. Wynn made a handsome profit on the car, but he lost the dealership, the only licensed Ferrari dealer in Nevada.

Steering

It’s Monday morning at Pebble Beach’s Spanish Bay Golf Resort. In the hotel’s circular driveway are Cobras and Porsche GTs. It’s not quite the caliber it was all weekend, but still extremely impressive.

A valet has just pulled up in Charlie Gray’s custard-colored Ferrari Portofino for the drive back to Los Angeles. As Gray struggles to find room for a suitcase in the meager space the Portofino calls a trunk, he points out his other Ferrari in the parking lot’s lineup—a black 812 GTS. “I’ve been coming to Pebble for 22 years, and ever since I was a little kid, I wanted to have the best car in the lineup at Spanish Bay,” he says, gesturing to the row. “And today, I have two.”

A platter of Lamborghinis: the car-maker celebrated its 60th anniversary during this year’s Monterey Car Week.

Gray has to move things around a bit to get the suitcase in the car, but he’s not bothered by the re-arrangement of his possessions. Maybe he’s still high from his latest pursuit.

The day before, Gray was waiting for one of the ubiquitous shuttle vans that ferry party-goers up and down the peninsula when he ran into Parris Mullins, from O’Gara Coach, who once sold Lamborghinis for Gray’s father. Small talk soon gave way to car talk, specifically the Bugatti Chiron, which was reaching the end of its limited, highly coveted production run.

“Well if you’re interested in that,” Mullins told him, “then I’ve got something for you.” Mullins then disclosed Bugatti’s Chiron replacement, an as yet unnamed, unseen, unannounced automobile with, Mullins teased, “a drivetrain and design architecture that is completely unexpected.” It was set to retail for somewhere close to $3.5 million.

Gray was in, committing to buy the new car before the shuttle bus had even reached its destination. At last it seemed the stars were aligning for him, softening the 10-year-old blow of the Porsche that got away. It’s one thing to have the knowledge and the means, it’s another thing entirely to have the relationship to make it happen. “To know it exists, to be in the position to get it,” Gray says, “I feel like I won the lottery.”

Gray is not unaware of how all this looks. He knows there’s a fine line between collector and crazy. “I feel like it’s kind of cringe sometimes to talk about the shit that you have. You’ve got to be able to laugh at yourself. It’s fucking silly what we do, the shit we chase.” He takes the keys to his Portofino from the valet. “But if you had a chance to buy a Picasso when he was alive, wouldn’t you?”

Mark Healy is a New York–based writer, editor, and podcast producer. He drives a station wagon