10 grand and some classifieds: Oh, the cars we’d buy…

We’ve all played the “imagine if” game. Some of us still play it, in fact. Every day.

We asked members of Hagerty’s Media Team the ultimate $10,000 question: “If you were given 10 large to buy a collectible car, what would you choose?” Some had to think about it, some knew the answer before they heard the question, and some got a little, shall we say, lost in time. Here are their picks:

Ben Woodworth, 1968–84 Saab 99 Turbo—My dad has always loved Saabs, for some reason or another (I should ask him about that sometime), and he gifted me his 1974 Saab Sonett III when I was in high school. I guess that’s where I get my love for the quirky Swedish carmaker. For as long as I can remember, I’ve really liked the Saab 900 Turbo. I’m sure my mom could dig up the grade school creative writing project I wrote, “What I would do with a million dollars.” Yes, folks, with a million imaginary dollars to spend on whatever I wanted, I chose a Saab 900 Turbo convertible (plus a house and probably a few other ridiculous things). But it wasn’t until a few years ago that I was introduced to the original turbo Saab, the 99 Turbo. I have Jeremy Clarkson and Top Gear to thank for that. It has a similar look to the 900, but with an added vintage vibe to it. I only get $10,000 imaginary dollars this time around, but my answer is pretty much the same: Saab Turbo!

Cody Wilson, 1990s Alfa 164S and 1988–95 Volkswagen Corrado—I would do a 2-for-1 special, with an Alfa 164S and a VW Corrado. Of course, I’d spend an additional $10k on maintenance every year, but the initial investment would be very reasonable. I’ve always loved both of these cars, even though their style is divisive. I fell in love with the Corrado in high school and almost bought a 164S about 10 years ago. I ended up going with an e36 M3, which I think was a smarter move. Either way, I’ve always been drawn to their ugly-chic style.

Davin Reckow, 1962–72 Chevrolet/GMC pickup—I’ll take an old pickup in a bowtie, thanks. There are still some reasonably priced ones out there.

Jeff Peek, 1958 Chevrolet Biscayne—Resisting the urge to buy another Mazda RX-7 (dang, I loved that car), I’d buy the very best 1958 Biscayne I could find, even if it took every single nickel of that $10,000. Two-door, four-door—doesn’t matter. I’ll never be able to afford an iconic 1955–57 Chevy Bel Air, but the ’58 Biscayne is the next best thing. I fell in love with the one-year-only design the first time I saw my friend Rudy drive up in his ’58 Biscayne. Classic, cool, and affordable.

Joe DeMatio, 1970–72 W114/W115 Mercedes-Benz—I’ll take a 1970–72 Mercedes-Benz, a 220/230/240 with the stacked headlights. I don’t really care much whether it’s a four- or six-cylinder, gasoline or diesel. I’m sure they’re all slow as molasses, so I’d be looking for a mint-condition sedan (common) or coupe (relatively rare). I like the size and the timeless looks by Paul Bracq, who also did the Pagoda-roof SL, among many 1960s Mercedes, before he became chief designer at BMW for the first half of the 1970s.

Jonathan Stein, 1999–2007 Kawasaki W650 motorcycle—If bikes are allowed, I’ll take a W650 Kawasaki. It looks a lot like a classic Triumph Bonneville, but it has modern mechanicals, a comfortable riding position, and will neither leave an oil trail nor die at an inopportune moment.

Justin Warnes, multiple Yugos—As a guy who already owns multiple Yugos, I would buy up as many of them as possible in an attempt to inflate the market. [Sure, you do that, Justin.]

Matt Lewis, 1955–57 Chevrolet wagon—I would be all over a well-loved Tri-Five Chevy (1955–57) wagon. I’m thinking I could find one for $5,000–$6,000, then I’d have some money left to make it drivable and fairly comfortable, find a small-block to swap into it if it needs an engine, spruce up the interior, and get some decent meats on the wheels. That’s what I’m talking about.

Nick Gravlin, 1966–72 Triumph GT6—Every time I see a picture of a Triumph GT6, I smile. Although it isn’t the fastest car or the best investment I can think of, I love the styling of these cars—a Spitfire with a roof, which looks like a tiny Jaguar E-type. It would be the perfect car to break up the monotony of using my daily driver.

Sandon Voelker, 1987–89 Porsche 944S—The S is my 944 of choice—more power than the standard model, without the troubles of the turbo. The naturally aspirated 16-valve inline-four loves to sing at high revs. That engine, linked to the rear transaxle, with a set of sticky tires, makes for one hell of a corner-carving machine. Low-slung hood line, flip-up headlights, bulged fenders … the 944 checks all the right ’80s styling boxes. Then again, I could be biased. I used to own one.

Stefan Lombard, Phil Hill’s 1952 Ferrari 212—I was looking up classifieds on the Internet the other day and came across this thing. Now I can’t get it out of my mind. Seems like a steal at the price!

Todd Kraemer, C3 Chevrolet Corvette—I would buy a C3 Corvette, from as early in the production run as I could get, in good condition. Stick shift, please. Corvette was the first car I truly fell in love with as a kid. These still had an outstanding design presence, which sadly started to drop off in the next two generations, even if they weren’t the fastest things on the road. And those pop-up headlights! Also, it’s a Corvette, so if you take care of it, the value is only going to go up.