One-Eyed Jack

One-Eyed Jack by Chris Green

Most people associate the name, Jack Dempsey with Boxing. He was the undisputed World Heavyweight champion from 1919 to 1926. He was a legendary puncher and won most of his fights by a knockout. Few fighters in history have been so feared. But I will always think of Jack Dempsey as my Biology teacher from 1991 to 1996. A different Jack altogether. At around five feet six, with monocular vision and a limp, a lighter and less aggressive Jack. He was a Dubliner and spoke with a lilting Northside accent, something I had not heard much of in my sheltered life in provincial England.

Apart from being a Biology teacher, Jack was a prodigious gambler. For much of the time that he was supposed to be preparing us for our exams, he could be found in Ladbrokes, the betting shop down the road from the school. He seemed to do well. He was the only teacher at the school to drive a Lexus. Whether he should have been driving at all with his impaired vision was a moot point.

I had developed a passing interest in horse racing and liked to pick out winners. One day, Jack found a copy of The Sporting Life from my paper round secreted in my desk. He took me under his wing and began to coach me in the subtleties of betting. He taught me how to assess risk and how to spot bookmakers’ tricks. He taught me when to punt and when to leave. Pick your moment, he told me, and never bet with your heart. He seemed to enjoy having me as a protégé. Later on, he introduced me to the ins and outs of Blackjack and Poker, of which he appeared to have an encyclopaedic knowledge.

Sadly, along with the rest of the class, I learned little Biology in his years of teaching. Every one of us failed our GCSE. Hardly surprising considering I was third in the class in the mock exam with just 9%. A lot of the questions were on the human eye, and we hadn’t covered that particular topic in class. The only surprise was that the school let us sit the real Biology exam. I did exceptionally well at Maths, however, and took it at A-Level.

If my memory serves me correctly, Jack was not even his real name. He was Seamus Dempsey. But to my knowledge, no-one called him Seamus. He was and would always be known as Jack. For all I know, his passport probably had him down as Jack. He appeared to be a solitary man, but rumour had it he had a wife and daughter. But given his gambling interests, I imagine they didn’t see much of him.

After I left school, I lost touch with Jack. I heard through the grapevine that following a year of particularly poor exam results, he lost his job. Just how bad could these be, I wondered? My guess would be that Jack wouldn’t miss teaching too much. He was probably looking for an excuse to leave to become a professional gambler. As for me, I went off to university where I was able to finance my stay through clandestine poker schools and reeling in fellow undergraduates with sucker bets. When it came to working out odds, it was surprising how easy it was to fool even the most intelligent students. I didn’t try it on with the Statistics students, but the rest were taken in hook, line and sinker. Popular I was not, perhaps, but unlike the others, I did not have to worry about whether my student loan would come through on time or how long it might last.

If I had applied the principles I used in gambling to my relationships, I might have fared better with the fairer sex over the years. But here the heart seemed to be boss. Every time I thought I had it made, I found the taste was not so sweet. Rachel was a stunner and clearly impressed by my success at the tables at the casino. I frequently came away with a substantial sum. She liked substantial sums, especially when they were spent on her. She was quick to put herself at my disposal, should I ever want a good luck charm hanging on my arm. It was difficult to turn her offer down, so I didn’t. I was smitten, and after a particularly fruitful night at the casino, I asked her to marry me. She accepted and for the next two years wrapped me around her little finger. I still had some money left after our divorce, but a fraction of what I had before it.

It would have helped if I had learned my lesson there and then. Once bitten and all that. Suffice to say, I didn’t. Next up was Natasha. I met Natasha on King George Day during the July festival at Goodwood. It followed a familiar pattern. I was celebrating my success on a long odds accumulator in the hospitality tent when Natasha made her presence known. Immaculately dressed and tall with long black hair and a summer tan, she was in many ways similar to Rachel. Yet this did not put me off. The similarity encouraged me. She moved in almost straight away. The strength of the feelings I developed for her took me unawares. I mistakenly thought she felt the same way, but it seemed she just liked my S-Class Mercedes and the holidays in the Caribbean. The weekends in Paris and visits to Fabergé. And the endless gifts I showered her with day in, day out. All those unimaginative, sad clichés. How could I have fallen into the age-old honey trap?

After Natasha had all but cleaned me out and moved on, I vowed to replace the heart on my sleeve with a more guarded stance. It was clear that my conspicuous consumption attracted the wrong kind of attention. If I were to avoid gold-diggers in future, I would need to be more discreet about how I celebrated winning at the races. I needed to take a leaf out of Jack’s book. In my experience, Jack consistently came out well from his wagers, but no-one would ever suspect he was raking it in. He was the most unassuming of men. While he may have been lonely as a result, at least he seemed to be in control of his finances and didn’t have to re-mortgage his house.

I had to see this as a turning point. I decided to seek help to get me through my crisis. I researched what was available locally and found there were dozens of counsellors and therapists advertising their services. It was a minefield. Cognitive behavioural therapy, psychodynamic therapy, neurofeedback therapy, hypnotherapy, kinesiology, behavioural activation. The options were endless. The human psyche was clearly going through a bad patch.

What does polarity therapy involve?’ I asked Celeste at the Alternative Therapy Centre.

It focuses on the interdependence of mind, body and spirit, and how they interact with each other based on the universal laws of energy, attraction, repulsion and neutrality,’ she said. ‘It balances the body’s flow of energy.’

What about trans-cranial magnetic stimulation?’

TMS is a non-invasive therapy that uses magnetic pulses to stimulate the area of the brain that controls your emotional reactions and regulates mood,’ she said. ‘Would you like to come along for a taster?’

I think I might leave it for now,’ I said.

Although Joe Louis did not qualify his practice method, I decided he would be as good a bet as any to knock me into shape. His name instilled confidence. For some reason, it reminded me of Jack.

Joe was old school with a vengeance. He belonged to the get a grip school of psychotherapy. He had no time for all this non-directive therapy nonsense that he said was taking over the profession. He believed in telling it like it is. Avoiding issues only wasted time. You ended up talking yourself round in circles. You needed to get right down to the nitty-gritty. If something was wrong, you faced it head-on. Joe must have been about eighty years old, but he still ran six miles before breakfast every morning. He had fought in the Second World War. Or was it the First?

Get over it,’ he would say each time I complained about something. ‘Pull yourself together, man. Don’t you realise, some people have real problems? Some are deaf, dumb and blind or have no arms or legs. You’re nothing more than a weekend paranoid.’

I learned early on that but wasn’t a word he acknowledged. Six sessions in, I decided I was ready to face the world on my own terms. From now on, I would be the master of my destiny. I was better.

But I was penniless and soon to be homeless. Some disciplined gambling was called for. No casinos, no poker, just carefully researched punts on the horses. Jack Dempsey maintained that there were never more than three or four safe bets a month at worthwhile odds. Despite these horses not being favourites to win, you could nevertheless pen them in as certainties. You would often find them at smaller meetings like Fontwell Park or Wincanton. Only those who knew what they were looking for would spot them. But once you knew how to do this, all you had to do was check the race fields from day to day. To keep the starting price respectable, you kept the knowledge to yourself and spread your stake around several bookmakers. Any other bets you placed, especially speculative accumulators or Yankees, were an indulgence. These were vanity projects. This did not mean you should ignore them, but you needed to understand they were just for fun. The more bets you planned to make, of course, the more background work you would need to do. Even so, the risk element increased. If you wanted to stay ahead, you stuck to the certainties.

But how was I to get started again? I could hardly go to the bank to ask for a loan. What is the purpose of the loan, they would ask? They would be unlikely to accept, to bet on My Lovely Horse in the 2:30 at Fakenham as a legitimate reason to lend money. Not even an understanding branch manager like Mr Cleghorn would approve that. I could pretend the money was to build an extension or install a new boiler, but I would be required to provide paperwork to back this up. As the house was being re-possessed, getting this would have been difficult. Instead, I sold my camera equipment and my scuba diving gear. Neither had had much use and in any case, I had nowhere to store them. With the proceeds, I could put a thousand on Light Fandango at 10-1 in the 3:15 at Hexham. It romped home. I was on my way.

Wish You Were Here at Catterick at 100-8 and Bunny Boiler at Haydock Park at 16-1 kept up the winning run. I was able to put a deposit down on a flat and buy a second-hand Corsa. Pulp Friction coming in at 8-1 at Wetherby enabled me to take a short break in Cornwall. I avoided all frivolous wagers. It was a minimum risk strategy. It was still possible to become overconfident and miscalculate a certainty, and when Heisenberg was beaten by a short head with two grand riding on it, I resolved to be more cautious. I would stake no more than five hundred at a time. Three bets a month maximum.

Restraint doesn’t suit everyone. Within a week I was climbing up the walls with boredom. I was doing Sudoku puzzles and watching Big Brother and repeats of Countdown. The longer I exercised self-control, the crazier I became. I bought a poncho and started reading bobsleigh magazines. I took up fork bending and painted the fridge green. I joined the Bee Gees fan club. I shaved my eyebrows off and was about to have a tattoo of a fairground scene on my forehead when I stopped myself. Enough was enough. This was madness. It was time to get back in the metaphorical saddle.

Five grand on the nose on New Romance at 20-1 with minimal research beforehand put me back on track. I followed it up with a successful night at the casino, and it was here I met Siobhan. She stopped me right in my tracks. The light was shining on her. Her long golden hair was bright and luxuriant. Perhaps I had had a glass or two, but I couldn’t take my eyes off her. She was more petite than Rachel and Natasha and had a gentler demeanour. She had fair skin, dreamy bliss-blue eyes and a smile like the morning sun. Nervously, I approached her and introduced myself. She seemed pleased and accepted my offer of a drink.

I don’t know why I came here tonight,’ she said. ‘I don’t normally come to places like this, but I was curious about what went on here.’

Neither do I,’ I said. ‘Well, I haven’t been here for a long time.’

I’m glad you are here though, as it is quite intimidating when you don’t know your way around. My friend Emma was meant to meet me here, but she cancelled at the last minute, and I was left stranded. I was about to leave when you came over.’

I suppose it is more of a man’s thing.’

I did not see much of my da while I was growing up,’ she said. ‘I spent a lot of time away at boarding school and summer camp. But I know he used to come to this casino, and he seemed to do rather well. You look as if you’ve had a good night too now.’

Beginner’s luck, I suppose,’ I said, not wishing to give anything away.

Ah, I see. I don’t think Da was a beginner,’ she said. ‘Not by a long chalk. He was obsessed with gambling. I suppose I’m here because I wanted to see what the fascination was. By the way, what happened to your eyebrows?’ 

The eyebrows? Do you know, I’ve been asking myself the same question?. But I’m sure they will grow back.’

I was surprised when Siobhan invited me back to hers for a nightcap, but naturally I was flattered. Things were looking up again. In the taxi, we found out a little more about each other. She had recently moved back to the area, having spent a year in Brussels. She worked in finance. Her family were from these parts, she said, although she did not elaborate.

Siobhan’s apartment was in a modern, purpose-built block on the outskirts of town. It was well appointed with brightly coloured furniture and abstract prints on the walls. She put on a shuffle of late night music and without asking, poured me a glass of Jameson’s Whiskey, along with one for herself. She said she was going to freshen up, she would be back in a minute. While she was out of the room, I noticed a selection of framed photos on a shelf in the corner. Curious, I went over to investigate. The pictures appeared to be random shots of Siobhan and friends, and there was one alongside them that looked like it might be an old family photo. Something about it seemed familiar. I picked it up to investigate. It hit me like a thunderbolt. It was so out of context, I had difficulty taking it in. There was Siobhan, and next to her was Jack. Jack was a little older than I remembered him, but with his slate grey herring-bone suit, his swept-back red hair, and his cloudy eye, he was unmistakable.

There seemed to be only one explanation. Siobhan must be Jack’s daughter. When she had told me earlier that her da used to be a teacher, I had thought no more of it. Why would I have? But what mysterious forces were at work to bring about this unlikely synchronicity? How should I read it? Was it a good omen? Did it bode well for a meaningful relationship with Siobhan or should I be wary?


It is early days, but all I can say is so far, so good. Things appear to be working out. Jack is back in Ireland. We are going over to Dublin to visit him next week. Perhaps we might have a day out at Leopardstown races.

Copyright © Chris Green, 2021: All rights reserved



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