Jack Ramsden’s fascination with horse racing dates back to his youth. He develops relationships with the horses and appears to know how to bring out their maximum potential, making him a genuinely successful gambler.

In the 1980s and early 1990s, Ramsden achieved thirteen consecutive winning years by utilizing performance figures and race times to determine which horses had the greatest chance of victory.

Initial Years

Ramsden did not have a typical upbringing; his father was a long-haul truck driver who was constantly on the road, and his mother was an inveterate gambler who cared more about winning than caring for her children.
However, because of his mother, he developed a passion for horse racing that would later lead to a lucrative career.

After graduating from high school, Ramsden became a stockbroker and remained so until the early 1980s, when he realized he was ready for a new lifestyle. Not only did Ramsden study form books for hours on end, but he always dedicated at least two hours every-day to analyzing his wagers to make sure they were appropriate for the current situation. In Oscala, Florida, where he resided with his wife, Josephine, he began working at a breeding and training facility.

After nearly seventeen years of marriage, Ramsden and Josephine divorced violently, forcing Ramsden to return to his hometown of Lexington, Kentucky. Together, he and his closest companion and business associate, Nate Washington, established a modest training business.

A Winning Tradition

Working with horses made it simpler for Ramsden to make informed wagering decisions, as he was continually searching for a horse with a 3/1 chance that had been given an 8/1 chance.

Working alongside some of the best-trained horses in the region gave him an advantage over other gamblers. He claims there are approximately forty of them per year, but they are difficult to spot. His methods centered on the understanding that a good horse is capable of a poor performance, but a terrible horse is incapable of a good performance.

Colin Webster, a professional bookkeeper, was recruited by Ramsden to advise him on every wager he placed or considered placing.
Ramsden pays him approximately $7,500 per year for his advice and for placing wagers with other bookmakers on his behalf.
Typically, Ramsden places multiple wagers at once, and on four separate occasions he has won over $300,000 by employing this strategy.

At one stage in his tenure, Ramsden set a record in the United States by winning thirteen consecutive years in a run. Long hours spent analyzing wagering lines and developing a rapport with the horses he wagers on have contributed to his success.