In the roaring, reckless Eighties, Terry Ramsden was the ultimate Thatcher-era upstart—a pint-sized, mullet-sporting, self-made mogul with a cockney twang and a gambler’s nerve of steel. “I’m a stockbroker from Enfield. I’ve got long hair and I like a bet,” he once quipped. And what a bet it was.
Born in Enfield, North London, on January 19, 1952, Ramsden had a natural instinct for numbers, risk, and, for a while, reward. He played the Japanese bond market like a virtuoso and dabbled in horse racing with the audacity of a man who never expected to lose. By 1984, he had scraped together enough winnings and investments to acquire Glen International Financial Services, a once-unremarkable Edinburgh firm. Three years later, Glen was turning over £3.5 billion, and Ramsden’s personal fortune had ballooned to £150 million.
By then, his royal blue and white hooped silks were a familiar sight at racecourses across Britain. With 76 horses in training and pockets deep enough to take on the bookies at their own game, he won—and lost—eye-watering sums that only added to his legend.
Take May 1984, for example. Just days before the Irish 1,000 Guineas, Ramsden snapped up an unseen filly named Katies for a cool £500,000. When she romped home at 20/1, he pocketed a cool £2.5 million.
Then came Cheltenham 1986, a week that should have made history. On Wednesday, his horse Motivator stormed home in what is now the Pertemps Final, putting £1 million in Ramsden’s coffers. But it was Thursday that could have made him an all-time racing legend. He had backed Brunico in doubles with Dawn Run for months. If Brunico had managed to catch Solar Cloud in the Triumph Hurdle, Ramsden would have walked away with £6 million. Instead, he had to settle for a lesson in the fine margins of fate.
Undeterred, he went bigger. He acquired Mr. Snugfit, a Grand National runner-up in 1985, and lumped £50,000 each-way at 8/1 for the 1986 renewal. Almost single-handedly, he drove the horse’s price down to 13/2 favoritism. Mr. Snugfit trailed home in fourth, but Ramsden still walked away with £150,000. Years later, he claimed the bet was ten times bigger: “The truth is I had half a million quid each way, quote, unquote. Anything else you hear is bullshit.”
His golden touch continued with Not So Silly winning the Ayr Gold Cup in 1987, but every gambler knows the tide eventually turns. Ramsden placed his biggest single losing bet—£1 million on Below Zero—and then the financial world crashed around him. When Black Monday hit in October 1987, Glen International crumbled. By 1988, he owed Ladbrokes £2 million and was banned from the sport by the Jockey Club. The high-flying stockbroker from Enfield had been grounded.
The fall was spectacular. In 1991, he was arrested in Los Angeles at the request of the Serious Fraud Office and spent six months behind bars awaiting extradition. By 1992, he was back in Britain, officially bankrupt to the tune of £100 million. A year later, he avoided prison with a two-year suspended sentence after admitting to recklessly soliciting investment in Glen International. But his past caught up with him in 1997 when he was convicted again—this time for failing to disclose £300,000 in assets. The Old Bailey handed him 21 months in prison, of which he served ten.
Yet Ramsden was never one to stay down for long. After his release in 1999, he quietly worked his way back into finance. By 2003, with the Jockey Club finally clearing him to own horses again, he returned to the winner’s circle with a two-year-old named Jake The Snake. Bought for a modest 17,000 guineas, Jake justified his owner’s faith by winning a maiden stakes race at Lingfield in November that year.
For Terry Ramsden, it was never just about the money. It was about the game, the thrill, the gamble. Sometimes you win. Sometimes you lose. But you never stop playing.
Photo: Freepik
