When discussing killings made in the market, the classic story seems to be that hypothetical person who invested $10,000 and bought 5,000 shares of Apple stock in 1985 for $2.00 a share, and held it for nearly 30 years, and watched that initial investment balloon to $6 million today.  Some people have done nearly as well in the classic car world. Here are some of our favorite killings in the classic car market:

1. Famous Ferrari



1964 Ferrari 250 GTO: In the February 1981 issue of Hemmings Motor News, a small ad appeared for a 1964 Ferrari 250 GTO, serial number 4091, from a dealer in Joliet, Ill. The asking price was $285,000 (about $733,000 in today’s money). Admittedly, it was not a small sum for a very pretty but obsolete race car. But had you taken the plunge on this rare classic Ferrari (fewer than 40 were made), your investment would be worth around $50 million today. A similar car was reportedly sold for that sum a few weeks ago. That’s about an 18% annualized return.

2. Bevy of Bugattis


(Aurélien Boffy)

Bugatti collection for a pittance: In 1963, fishing equipment heir John Shakespeare dumped his collection of 30 classic Bugattis to a predatory French collector for a reported price of less than $250,000. The collection might today be worth close to $100 million, and included one of six Bugatti Royales, one of the most expensive cars on the planet. Shakespeare himself had scooped that one up for just $9,000 in 1956.

3. Sister snakes



A pair of Cobras for less than 100 grand: In the same issue of Hemmings Motor News referenced above, you could have purchased a pair of real Shelby Cobras for under $100,000 — just $30,000 for a small-block 289 Cobra and $60,000 for a big-block 427. Today, they’d be worth about $900,000 and $1.3 million, respectively.

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