One of the most successful horse race bettors in the history of the industry, Terry Ramsden made a fortune from his various gambling wagers throughout his career, particularly in horse racing.

From Enfield, England, Ramsden was the son of a telephone engineer, and grew up in a generally middle class neighborhood. After getting his first job as an insurance clerk, Terry quickly realized that he would never meet his high aspirations or make the kind of big money that he wanted to by working for someone else, so by the young age of 19, he was already self-employed and making £25,000 in his first month of work.

Ramsden got an early start to his horse race gambling career as he started off with lower stakes wagers on various horse races. From there his love for the sport grew quickly, and he developed quite a talent for picking the winning horse. Due to his great success in horse race betting, Ramsden purchased Glen International in 1984, a company that was based in Edinburgh. He changed the company to focus more so on horse races and picking winning horses consistently, which he himself was already very skilled at.

In his first year of business with his new company he made £18,000. A solid start but only a fraction of what his true aspirations were. Three years later he would recognize his success as his company made around £3.5 billion pounds. At the peak of his net worth, he was said to be worth around £150 million, and was at a time the United Kingdom’s 57th richest person.

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Between 1984 and 1987 while living in Japan is when Ramsden really hit his stride of success in betting on horse races. He grew his fortune to around £100 million by 1986, and he owned several lavish houses, including one posh home in Los Angeles, as well as having around 100 horses. That same year, Ramsden bet on his own horse to the amount of £500,000 and his horse placed 4th in the race, which earned Ramsden a hefty £1 million profit from the wager.

Ramsden’s success eventually came to a halt around 1987 as he was greatly effected by the stock market crash that year. This seemed to be the beginning of the end for Ramsden as he then lost around £57 to £58 million on horse racing wagers, in addition to losing around £100 million in capital losses.

All of this misfortune culminated in 1991 when Ramsden was sentenced to six months in jail for fraud, and was awaiting extradition back to the UK. By 1992 his debt had grown to £100 million that forced him to declare bankruptcy, and plead guilty to bad business practices with his company Glen International. He was given a 2-year suspended sentence for his actions.

As things started to crumble around him, Ramsden was still not out of the woods yet, and would eventually see prison again as he was sentenced to 21 months of prison for breaking the Insolvency Act when he was found to be hiding £300,000 worth of assets. He was released after only serving 10, but upon his release he had lost the support of a number of close friends, and his wife and son also distanced themselves from him.

At his peak he owned 30% of Chelsea F.C., one of the most valuable sports teams in the entire world, and he also owned all of Wallsall F.C. Worth in excess of £100 million at a time, and one of the richest men in all of England, he was well respected from all his peers and throughout his industry, and has lived as storied of a life as they come.

From mediocre beginnings to one of the most prolific horse racing bettors to ever wager on a race, and then to serving multiple prison stints, Ramsden has done it all. Despite his misfortunes later in life, he will still always be remembered as one of the most successful gamblers in history, and arguably England’s greatest sports bettor. Despite his degrading wealth and tarnished record, he helped shape the landscape in the horse racing industry, as well as the gambling industry into what it is today.

If you enjoyed his story then please read about other famous and successful sports bettors:

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