Shelby 289 Cobra vs. Mercedes 300SL roadster: Which is the smarter buy?

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Neil Jamieson

I have a friend who owns a small stable of largely sub-$100,000 sports cars from the 1950s and ’60s. He is a brilliant engineer and tends to look at things in stark contrast to the way I do, which is to say he actually thinks them through, often on a molecular level. He came to me recently with a philosophical and well-considered line of questioning regarding his next potential acquisition. He recently retired and wants to celebrate the milestone with the purchase of a Shelby 289 Cobra or a Mercedes-Benz 300SL roadster. Each is an aspirational car that he’s always admired; now he wants to know if he should do something about it.

Everybody thinks about certain aspects before buying any car: Can I afford it? What will I do with it? Will I enjoy it? Will it be hard to maintain? All of those questions were apparently easy for my friend to reconcile. The philosophical aspect came down to two things that affect all of us: First, none of us is getting any younger. Second, what will our heirs do with the cars when we are gone?

My friend figures he has 15 years or so to enjoy a Cobra or 300SL before he reaches a point of diminishing joy. His wife, a car lover as well, is in the same boat. Their three grown daughters, however, have no interest in taking over stewardship of any of the cars when the time comes.

So, as a practical matter of being able to offload a 289 Cobra or 300SL in a decade or two, my friend wanted to know which car had a better chance of remaining desirable. I know which one I’d like more, but for once, I decided to apply science to something and dug into the wealth of Hagerty data for the value histories of each car, along with the demographics of those seeking insurance quotes on them.

I also wanted to know what the demographic shift might mean for other benchmark classics compared to up-and-comers: Big-block, high-performance 1965–67 C2 Corvettes vs. 1990–95 C4 ZR-1 Corvettes; and 1970–73 Datsun 240Zs vs. 1993–98 Toyota Supra Turbos. The results follow.

Comer Column Values Illo
Neil Jamieson

As for the Cobra and the 300SL, the data showed what I suspected it would: More younger people gravitate toward the Cobra than the 300SL. How many more? Roughly three times as many Gen X and millennial buyers as boomers, a fairly significant amount. And that is almost a direct swap with the number of pre-boomers who prefer the 300SL. Quotes from boomers between the two cars were nearly identical. Translation? The Cobra should have more buyers in the future as Gen X and millennial enthusiasts continue to buy and drive, while pre-boomers stop buying altogether and the bedrock of 300SL purchases are left to boomers.

One thing the Cobra has going for it is the Shelby American Automobile Club’s World Registry. In this day and age of “new” buyers, who rely on research and crowd-sourcing to validate cars rather than years or decades of personal experience, the fact that every Cobra is thoroughly documented encourages peace of mind—and adds value. Such broadly accepted documentation is something many collector cars simply lack. Just imagine being able to open a book so you could disprove all but 3754 of the 19,000 claimed “real” 1967 427/435 Corvettes!

The median value chart also bears out this Cobra vs. 300SL prediction. Mercedes 300SLs have been declining since 2015, while Cobras—other than a brief dip in 2019—have been going up steadily. Do these two things illustrate a generational shift driving up Cobras and a simultaneous graying of the buying pool pulling down 300SLs? Maybe it’s the perceived cost of ownership or the expense of a restoration? Time will tell.

As for my friend, he is still in seclusion, working out the emotional math on a whiteboard, and hasn’t bought a car yet. In the meantime, we could all benefit from using even just a little of his methodology when it comes to the future viability of an aspirational purchase. After all, we are only caretakers of these lovely things for so long.

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