Heads or tails for your Rolex? Kicking a ball into a skip for a £15K watch? Sportsmen’s crazy watch bets

Luke Benedictus

You might blame it on the betting culture within professional sport. Or the competitive personalities of top sportsmen that make them that much more willing to take on the bookies. Or maybe it’s simply the fact that many professional athletes are young men on huge wages with far too much free time on their hands. Whatever the reason, the world of professional sport is rife with degenerate gamblers.

Golfer John Daly famously estimated that he lost up to $57 million USD between 1991 to 2007, sometimes playing seven simultaneous hands of blackjack for between $5,000 and $15,000 a pop. An entire book was written about Michael Jordan’s obsessive love for a punt.  In Michael and Me: Our Gambling Addiction… My Cry for Help, Richard Esquinas claimed that Jordan owed him $1.25 million from golf bets. But in the world of British football – where, it’s fair to say, there was some pretty stiff competition – one of the most notorious gamblers was Paul Merson.

“The Merse”, as he was known on the terraces, was a playmaker with bags of flair and imagination who dazzled the crowds during his career at Arsenal, Middlesbrough, Aston Villa and Portsmouth. Off the pitch, however, Merson struggled with alcohol issues and cocaine. But his most problematic vice, he admitted, was gambling.

“I didn’t stop until, eventually, I’d lost everything I’d ever had – close to £7 million, including houses, cars, marriages, my entire pension and my self-respect,” Merson wrote in The Daily Mail.

One knee-jerk bet saw Merson losing the watch off his wrist.  “I once lost a top-of-the-range Rolex to a friend in a game of heads and tails when we were drunk in Spain,” Merson told The Sun. “He took the watch and then got robbed. But you can’t have a bet and moan if you lose.”

Losing a Rolex in a game of heads and tails is clearly madness. But it isn’t so surprising given the results of a study that revealed that sportsmen are three times more likely to be “problem gamblers” than the average man on the street.

Merson’s daft Rolex bet is also a reminder of another mad wager that involved another British footballer and a watch. David Bentley was a talented midfielder who perhaps failed to realise his full potential. But, on the positive side, he did once win an “expensive watch” in spectacular style – by kicking a ball off the top of a building and into a nearby skip.

“It was when I was at Tottenham,” Bentley told Four Four Two. “We’d lost on the Saturday and I was having a bad time. Red Bull asked me to their offices in central London to do a stunt. I wasn’t interested but went along anyway, and the next thing I know I’m on the roof with a ball. I said I was going to hit a red bus, which worried them as they thought I might kill someone.

“Instead, we aimed for a skip. Bang – it’s gone in. I’d bet my agent his expensive watch and the ball went straight in. It got lodged and just stuck. It was probably the best thing I ever did!”

Sadly, we don’t know what type of watch Bentley won with his high-rise effort. But he did mention it was purportedly worth £15,000.

Another sportsmen who was apparently willing to put his wristwear on the line was Tyson Fury. The Gypsy King’s much anticipated bout against Anthony Joshua currently looks unlikely to go ahead. But Joshua did spar against Fury many years ago when they were both young heavyweights on the rise.

As Joshua told The Sun: “I was reading in Boxing News he [Fury] was going around London gyms asking if anyone knocks him out they get to keep his Rolex.

“Me and him had a straight war. We both have heart. I didn’t get to knock him out. He said afterwards ‘Watch out for this kid, he will be champion of the world one day’.”

Fury’s prediction about Joshua would eventually prove right. Luckily, he managed to hang onto his Rolex, too.