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2. 1963 Ferrari 250 GTO: $70 million

Ferrari 250 GTO
1963 Ferrari 250 GTO | Michael Cole/Corbis via Getty Images

In 2018, the vintage Italian sports car broke a record when Chicago’s David MacNeil, the founder/CEO of WeatherTech, bought it for $70 million. As CNN explains, “It’s extremely rare for an owner to part with one at any price” because only 39 were built by Ferrari between 1962 and 1964.

At the time of MacNeil’s purchase, the auction chairman James Knight said, “The Ferrari 250 GTO is the motoring market’s equivalent of Van Gogh’s ‘Sunflowers.'” Who else owns this legendary vehicle? Ralph Lauren, Pink Floyd drummer Nick Mason, and British billionaire Lord Anthony Bamford.

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