The 10 Biggest, Greatest and Most Expensive Heists of All Time

Have you ever wondered about the most expensive heists of all time? While we know we shouldn’t be endorsing crime, some of these heists take so much skill, bravery, and cojones that you can’t help but side with the heisters, at least a little bit. Featuring priceless art, gold bullion, straight cash, or even royal crowns, here’s our rundown of the biggest heists, the greatest heists, the most expensive heists, and the most audacious heists in history.

10) The Wilcox Train Robbery

Loot: $50,000 ($7 million today)

No “greatest heists ever” list would be complete without a good ol’ fashioned train robbery. And Butch Cassidy and the Hole in the Wall Gang’s great 1899 Wilcox Train Robbery is one of the most iconic of them all.

Just like anything great in the Old West, the Wilcox train robbery started and ended with dynamite. First, they dynamited the railcar holding the lockbox, then they dynamited the tracks to prevent pursuit, and then just when anyone else would start wondering if they had used enough dynamite for the day, the Hole in the Wall Gang blew up the lockbox too. They successfully escaped on horseback using fresh horses prepared for their getaway. The story has left its indelible mark on pop culture, much like the dynamite – which left distinctive burns on banknotes that were found from New York to New Mexico in subsequent years.

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