Is there such a thing as an affordable classic or a good deal during Monterey auction week? Watching collectors and enthusiasts flock to the numerous auctions searching for a special, once-in-a-lifetime deal is like watching a professional goat rodeo. If you are a chaos junkie, this is for you, but making sense of this madness can be taxing, perplexing and exhausting — even for seasoned pros.

Imagine every dealer, collector, punter, enthusiast and wannabe all gathering under a tent, vying for that special auction lot. Everyone is hoping, thinking and praying that maybe, just maybe, they can grab a bargain or a deal when the collective masses fall asleep, blink or go for their third cocktail. The fantasy is that I’ll be the only one paying attention when the gavel falls! Yeah, that’s about as likely as getting a winning Powerball ticket.

Treasures still gleam

Yet despite all that, sometimes something special does happen during this wild weekend in California — there are golden opportunities to buy cars that you wouldn’t normally even see. In a perfect world, the particular treasure that you’ve been searching for can be acquired at a sensible price and maybe even at a small discount — think 5% to 10%.

I feel that the following four cars were bought astutely and may be damn hard to replicate in a reasonable period of time at these same prices, if at all. I’ll go from least expensive on up:

Lot 65, 1966 Jaguar XKE Series I 4.2-liter coupe, sold for $93,500 at Gooding & Company’s auction on August 20

You might be thinking, what’s so special about a Series I Coupe at this price? This car was not a steal by any measure, but try and find another one-owner, California Black Plate E-type with a stonking great original interior, superb panel fit and mostly original paint. This car felt every bit like the Swinging Sixties icon that it was, and it will be really hard to duplicate for the passionate originality guru. The E-type world is overrun with available inventory, most of it space junk.

I have to admit that I tried to buy this car, as it was late in the auction and I was hoping no one was paying attention. As if! I couldn’t get the deal I wanted, and I was envious of the fellow with the deeper wallet.

Lot 130, 1958 Aston Martin DB Mark III drophead coupe, sold for $247,500 at RM Auctions on August 19

Lots of pre-auction press followed this particular lot. Sadly, this lovely Aston Martin had a strong, smelly media-related funk attached to it that wrecked any chance of it going above catalog estimates. I think this car was bought at a real wholesale price. For those of you unfamiliar with the story, it was owned by the brother of the now-infamous and unloved Bernie Madoff. Let’s face it; if a car could possess extra-bad karma, this was the ride. Quite a few Aston lovers I spoke with refused to be interested in this car, just on principle alone.

“Hey, I just bought a Madoff car at auction!” This is not the thing you want to shout out and brag about anywhere on the East Coast, and therein lies the rub, but a rub that hurts people only in the U.S.

A fellow Aston dealer from the U.K. asked about the car after the auction, and he wondered why it went so cheap. I explained the story. When he uttered the words, “Who’s Bernie Madoff?” I realized that perhaps a smart European was the lucky new owner.

This was a straightforward, decent older restoration, and it was a car that you’d be happy to own.

Lot 39, 1985 Ferrari 288 GTO, sold for $748,000 at Gooding & Company’s auction on August 19

The 288 GTO was Ferrari’s first “modern” supercar, it was their first real foray into carbon fiber and it was the first Ferrari to re-use the magical GTO moniker.

With just 272 examples, they are few and far between compared with many other modern Ferrari supercars. More importantly, the market on these particular cars has lit up again in 2011, with some private sales on some very-low-mileage cars going well above the $1m mark.

This car checked all the boxes for a 288 GTO, except it was not the lowest-mileage example, with just under 25,000 kms (15,000 miles) showing. So what? If you’re actually going to use this car occasionally, this was the perfect buy. If you add 5,000 miles to a car like this over a few summers, this is the smart buy.

Upon inspection, this was a flawless car, down to the imperfect original paint. This particular car came from a great collector who spent a great deal of time and effort making sure this was a true 99-point example. The new owner has a great car here.

Lot 440, 1957 BMW 507, sold for $1,002,500 at Bonhams’ Quail Lodge auction on August 19

1111-Affordable-4OK, $1m-plus does not land a car in the “Affordable Classic” range for 99.9% of us. I get that, believe me. I’ve listed this car for the simple reason that this market is red-hot, and this particular 507 could have been sold ten different times for this price during this weekend.

Hmmm, let’s say we rename this page “Most Desirable Classic” for these few paragraphs. This car has a quality restoration from one of the best shops. It also has Rudge wheels (albeit repros), a hard top and a great color combination. This car is beautifully presented, with no excuses. I personally don’t care for these cars for myriad reasons, but I liked and admired this one, even though it is an early Series car that I wouldn’t fit in. This car falls into the column of “I want one and it’s here in front of me, so how long do I wait to get another one?”

This was one of Bonhams’ star cars for Monterey, and this car did not let them down. These cars are the ultimate post-war BMW collectible, and they appeal to buyers all over the globe.

This is a just my own snapshot of four cars that I think were smart buys for one reason or another. The exercise here proves that even in the most car-centric spot in the universe, overrun with thousands of like-minded manic enthusiasts, you can still end up with a “deal” if you really put your mind and wallet to it.

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