This article first appeared in the Nov/Dec 2013 issue of World Gaming magazine.

Okay, so you are not afraid of betting a few thousand on your favorite soccer team and you once lost a wager forcing you to do fifty push-ups in front of your opponent. We’ve all been there. But where do you draw the line when the stakes escalate far beyond mere money? Mutilation? Risking your life? The dark and morbid side of gambling’s history contains everything from mass murders, human sacrifice, the Pentagon’s “terrorist casino” and the hospital from hell … welcome to the first in a series of articles in WGM on the world’s worst bets!

Life comes with risks. I have so far survived three crashes that have totaled either my motorcycle or car at the time; have jumped the world’s three highest bungee jumps on three different continents; and the umbrella stand in my hallway consists of the casing from a former Soviet 122mm howitzer shell – a memory of my time serving as a warrant officer with the United Nations Forces in the Middle East. I can tell you from experience that dismantling such a piece of ammunition containing about six kilos of first-rate explosives – not to mention a highly volatile detonator liable to go off at the slightest bump – under field conditions is a hard-to-beat 10-minute thriller.

There is no escaping the fact that you will have to take some risks in life. Be it as simple as crossing the street or as complex as getting married, newspapers around the globe can tell you stories of people who have “bet” on the wrong choices. But there is a difference between what we must face in our everyday existence and the stakes some are willing to raise it up to when the “care to make it interesting?” question is asked.

According to Steve Mandiach’s biography of the famous American stuntman Evel Knievel, during a game of golf at the Seacliff Country Club in Huntington Beach, California, in 1975, Knievel made a notorious bet. Just as he was to tee off at the 18th and last hole, Knievel turned to his opponent and said, “Let’s have a bet for $7,000 on this last hole; and whoever does not want to pay up has to cut off his finger.”

Knievel’s opponent, a well-known golf hustler, agreed. Knievel, an 8-handicapper back then, made par on the hole – but his opponent made a birdie. Knievel was sick of having previously lost a lot of money so decided to cut off his finger instead. One of the staff at the clubhouse helpfully supplied a small axe, held Knievel’s finger steady with the help of a roof shingle to protect the hand and sliced off the tip, which “hurt like hell”. A grimacing Knievel put the fingertip in his pocket, grabbed a taxi to the nearest hospital and had the tip sewn back on although he was left with a nasty scar as a reminder.

According to Knievel, a couple of days later his opponent turned up again and suggested another match. The stuntman replied, “OK, but this time we play for arms, not fingers!” The other player refused to take that particular bet.

Another very much talked-about wager of its time was the one struck around the year 40 AD between the infamous Valeria Messalina, the third wife of the Emperor Claudius, and Scylla who was the most renowned prostitute in Rome. The subject of the wager, according to the historian Pliny in volume X of his Naturalis Historiæ, was which of the two women could withstand having continuous sex with the largest number of men during a 24 hour period from a “supply” of slaves, commandeered soldiers and volunteers. Pliny reports that Scylla was eventually forced to give up due to body pains, but Messalina “went the distance” and could triumphantly collect on the bet after notching up 25 partners.

If you think the above wagers are bad enough, they are nothing compared to what will follow in Part B of “The World’s Worst Bets”!