Who Is the Richest Gambler of All Time?

Who are the richest gamblers ever? That’s a good question. Mainly because the answer is complicated. Are we talking the gamblers who have won all their money gambling, or are we talking polymaths who make money at whatever they turn their hands to, including gambling?

Let’s go with that latter description. Anybody can win $200 million with a single lottery ticket (well, maybe not you or me, but anybody else ). But it takes someone good at many things to accumulate hundreds of millions of dollars over a lifetime.

Unlike tomorrow’s richest gamblers, there was no online gambling in the US to hone one’s skills. Not back in the day. The “internet” back then was the telephone, and computers were something major universities and the federal government used. Some of these people were making millions before color television caught on.

That said, what follows are people who made money in various fields as diverse as real estate and software development—but virtually every one of them established themselves as a titan of the gambling world. 8. Robert Moore, $200 Million (Horseracing)

Just making it onto the bottom rung of our list of gamblers who made the most money is Robert “Bob” Moore.

One of the groups of mathematicians and punters in Hong Kong’s Happy Valley horseracing milieu, Bob Moore, brought a mania to gambling that was not the better for the copious amounts of cocaine he imbibed.

According to legend, in 1983, Moore arrived in Hong Kong with $5 (AUD) in his pocket. He quickly found work with Bill Benter and Alan Woods, who ran a successful horseracing “consultancy.”

The native New Zealander earned his keep with his careful review of horseracing videos to determine which horses might have won a race otherwise but were impeded in some way (bump, stumble, or otherwise blocked) that precluded the win. His input dramatically improved the accuracy of the Benter/Woods betting algorithms.

Moore had a chaotic relationship with both Benter and Woods, working with both, then when the two split up, for Benter, then for Woods—during which time he allegedly attempted to sell Benter’s racing data to Woods.Moore was a […]

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