Confessions of a political gambler 

What could be more exquisite than the life of the professional gambler? I began my career in 2016 with a modest punt of £1,000 on the London mayoral election. Bingo. Sadiq Khan won and I banked a profit of £100. Then Brexit. My guess was that the pollsters had overestimated support for Remain and that the country was keen to evict the conjoined twerps, David Cameron and George Osborne, from Downing Street. The referendum was our chance to vaporise both their careers simultaneously. One cross, two graves. That’s what happened. And I cleared another tidy sum.

But I was haunted by a wager I’d laid in the winter of the same year while watching Fox News over a relaxing pint of Tesco claret. I bet £800 on a Donald Trump victory. Over the ensuing months I watched in disbelief as the candidate set about destroying his reputation with improvised asides and unforced blunders, including a claim that he could ‘shoot somebody’ on Fifth Avenue without harming his popularity. Trump was a lost cause. So was my money. Hillary Clinton confirmed the news in her pre–victory statement on 26 October. She tweeted a picture of herself as a schoolgirl alongside the caption: ‘Happy birthday to this future president.’ She’d already won. It was over. I cursed the day that I’d ever started gambling. I was a fool. A dunce. A clueless moron.

And then the results came in and everything changed. Hillary was out. Trump was president. And I was a genius. A maestro. A visionary. I could gaze into the future and anticipate events before they happened. And there was money to be made as well.

The Trump result was a one-off, obviously, and I devised an ultra-cautious strategy. Choose dead certs and stake large sums at very short odds. That would shield my money from danger. By betting on council elections and city mayoral contests, I could turn my gift of clairvoyancy into a steady income.

Theresa May called an election in the spring of 2017 and Nostradamus got to work. The projected Tory landslide seemed unlikely to me and I expected the Conservatives towin a decent but not a massive majority. Maybe 20 or 30 seats. Fifty was possible. A hundred was a fantasy. Using my steady-Eddie strategy, I placed a large stake on the least risky outcome.

Polling night arrived and I showed up at a drinks party in Westminster full of political hacks and spads who were seated around a screen tuned to the BBC. I nudged the wonk beside me. ‘You know, I’ve had a little flutter on the outcome,’ I said. ‘How much?’ he asked. My answer surprised him and he passed the news around the room and it spread rapidly into the surrounding corridors. As the main room filled up with people, I noticed a few of them whispering and pointing in my direction: ‘It’s him. Over there. The guy who bet 6,000 quid on the Tories.’ Someone asked me how large a majority I expected but before I could answer the bongs began.

It was ten o’clock. David Dimbleby appeared. ‘The Conservatives are the largest party. Note – they don’t have an overall majority at this stage.’ A weird singing noise began in my ears and I felt myself gulping uncomfortably as I gazed at the TV. ‘No overall majority.’ I stared and stared at the caption at the base of the screen, hoping to make it disappear by sheer eyeball power. At the same time I tried to compose my features into a smile of triumph and yet I could hear myself coughing and clearing my throat involuntarily. And I kept folding and unfolding my arms in a vain search for a relaxed position in my chair. All eyes were on me. I looked back at the circle of party-goers and I saw my ruin written in their expressions. Pity, shock, wonder, ridicule, disgust, contempt. They knew. They could tell from my panicking eyes and my fidgety demeanour that I’d blown it. Six grand. Six sodding grand had vanished.

But why? My plan had been so reasonable, so wise, so shrewdly insulated from risk. Stake a large sum on a dead-safe outcome – a simple Conservative majority – and collect a nice little profit. But the Tories had let me down. Those bungling idiots. All they needed was a handful of extra seats. And they’d failed. The bunch of morons.

The next day, following my public humiliation, I closed my online account and resigned as a soothsayer. I made one intriguing discovery from my gambling career. Every wager, whether it succeeds or fails, delivers a stab of anguish to the heart. If you win, you feel that you should have bet more. If you lose, you feel that you should have bet nothing. Even in triumph you experience no joy, no respite, no escape from the guilt and the curses of self-laceration. Every winner in the casino knows that his haul would have been twice as big if only he’d been twice as brave. Truly it’s a dreadful business. And I’m glad it’s all behind me now. Well, nearly. I’ve put a hundred on Kamala.