So You Won The Lottery: What Cars Should You Buy?

Of the hundreds of millions of us who likely bought Powerball tickets in an effort to become a billionaire, only three of you prevailed. Before taxes, if you chose the lump sum option, you will each receive around $383 million—a decent payday, it’s fair to say, and enough to buy any car of your dreams.

But what cars should you buy?

For those of us that didn’t win, I don’t blame you for stopping reading and crying into your stained pillowcase. After all, in our mind, we’d already purchased Hugh Hefner’s mansion—along with his flock of prized peacocks and African cranes—and lined its garages with the most exotic sheet metal imaginable. And, hopefully, we bought a new pillowcase.

For you lucky souls that did win, many tough choices lie ahead. After taxes, your payout may be less than you originally hoped, which means those choices must be wise. The Playboy mansion? It’s on sale right now for $200 million, which means it’s probably a poor purchase. Plus that grotto will be filthy, and peacock food ain’t cheap.

In the grand scheme of things, cars aren’t that expensive—unless you’re seeking a Ferrari 250 GTO, in which case you’re an idiot and will be broke within 12 months. Which is why my first choice of vehicle, regardless of the size of you family, would be the levelheaded, sensible 2016 Volvo XC90.

It costs just $66,000, fully loaded (“fully loaded” is how you used to order your baked potatoes, now it’s how you buy cars). Why an unsexy Volvo? Well, thanks to an influx of Chinese Yuan, Volvo’s are now exceptionally sexy. It has three rows, and leather that feels as if it’s fresh from the cow that birthed it. The starter button looks like a piece of fine jewelry, and for the first time in human history, the infotainment touchscreen actually works. Simply put, it rivals a vastly more expensive Range Rover, and yet it feels more advanced. It was our 2016 Yahoo Autos Ride of the Year, and by owning one, it’ll offer the illusion that you’ve remained down-to-earth—despite the 17 butlers hired to refuel it and that fancy hat you insist on wearing that’s made from organic leprechaun beard.

( I am, genuinely, excited for you, btw—not bitter at all. Anyway, oceans are full of sharks, and I never much cared for Hawaii’s heat. In fact, losing helps me take comfort in all that I have. Like my old swim coach used to lie, it’s the taking part that counts. We’re already winners.)

Back to cars: You’ve made the wise choice of a Volvo. Now let’s make a less wise choice.

A 1992 Lancia Delta Integrale Evo 1 Martini 5. On the surface, this might seem like a stupid choice. In fact, you may never have heard of this car. It was an icon in Europe, thanks to its dominance in the World Rally Championship. The “Martini 5” part indicates it derived from a 400 unit special run that celebrated Lancia’s fifth consecutive WRC championship. It’s also decked out in the famed Martini livery, which is a colored sticker that instantly doubles the machine’s value.

The car above, with just 26k on the clock, will set you back $115,000. You’ll then have to ship it to the U.S., which won’t be cheap, where you’ll notice it’s right-hand-drive and shifts via a stick. That means you’ll crash, and thus be unable to find parts to fix it. And even if you don’t, it will breakdown every 13 miles.

I forget why I love this car so, but god dammit I do.

Next: Let’s do a cliché Ferrari, because you’re now a rich bastard that wants to show off, but not so much that your family disowns you. A bright orange Lamborghini Aventador SV is probably too much. (Although you could always buy a new family?)

Given this is likely your first Prancing Horse purchase, you’re permitted to buy one in red. After which, you may never buy a red Ferrari again. Ever. The Ferrari you should buy is simple: a 2014 458 Speciale. It arrives for around $240,000, and is basically a rolling sex machine with 597 horsepower. It’ll trounce most any of its rivals, and yet it remains somewhat usable outside of a racetrack—if you call zero to 60 mph in 2.8 seconds usable.

Let’s be sensible again: We’ve got the cushy three-row SUV, the inappropriate Italian rally car and a wildly fast Italian Ferrari. What we need now is an executive sedan that you can drive (or be driven in), one that makes you look like a boss. For this, there’s nothing better than a 2016 Mercedes-Maybach S600. It’s the obvious choice, I know, but sometimes obvious is best. On the outside it appears understated yet classy, while on the inside it looks like Warren Buffett’s living room. A new Maybach today only costs $189,350.

Our total costs up until now are around $613,440. That’s not bad for an executive sedan, a modern supercar, an impractical toy, and a three-row SUV. With hundreds of millions in the bank, you can probably afford to let loose.

So we’ll buy a 1971 Hemi Cuda. Why? Because it’s ‘Merican, and it’s the holy grail of muscle cars—the machine that, thanks to fuel mandates and rising insurance costs, ended an era of automotive culture, the likes of which we may never see again. A good’un may cost hundreds of thousands, but a great one could cost up to a million.

I’d also buy a V-8 Lotus Esprit, mostly because it’s stunning and has a weirdly charming character—despite the fact it’ll never work. I’d buy an E30 BMW M3, too, and a 2016 Ford Shelby GT350R Mustang—because it’s a revelation and one that’s value will skyrocket. (Maybe an old Alfa, too?)

What I wouldn’t do is buy a Veyron, or anything else “Money Mayweather” owns. (Wait, Floyd owns a Maybach S600. Scratch that.) Rather, I wouldn’t buy anything worth multiple millions of dollars. You can get all the automotive pleasures you desire without spending anything like that. Hell, the new Miata is a joy to drive, and the “Club” model starts at just $28,600.

I picked the Lancia and the Esprit because they’re cars I’ve adored since childhood; both graced my bedroom wall, along with a Jaguar XJ220 (add that to the list, screw what I just said about price). Buy the cars you’ve dreamed about, whether that’s a DeLorean, a Ford Cortina, or a frickin’ Weinermobile. Veyrons and tuned Lambos with 2,000 horsepower are for posers, and while I don’t know you personally, I can sense you’re better than that.

And remember, money can disappear as fast as it arrived—just ask Tyson. So be wise. Invest. Peacocks make crappy pets anyway.