Professional Gamblers: Who Is Simon Cawkwell?

I'm still thumbing my way through Mike Atherton's Gambling: A Story of Triumph & Disaster. A fascinating read, where I seem to bump into gamblers of much appeal but who I have no knowledge. It always makes for a great read when it's unexpected.

Many readers may have heard of Simon Cawkwell. 

If you haven't, then take a read and watch the video too.

Simon Cawkwell, widely known by his moniker "Evil Knievil," is a prominent British figure renowned for his activities in the financial markets, particularly in short selling, as well as his ventures in gambling. Born in October 1946 in Oxford, England, he is the son of historian George Cawkwell. Simon received his education at the Dragon School and Rugby School before training as a chartered accountant.

Financial Market Activities

Cawkwell's career in the financial markets spans several decades, during which he gained notoriety for his short-selling strategies. Short selling involves borrowing shares to sell them with the intention of repurchasing them at a lower price, thereby profiting from a decline in the stock's value. His first significant short position was in 1973 with MFI Group, where he capitalized on the company's share price collapse from 150p to 10p. Over the years, he has made substantial profits by shorting companies such as Northern Rock, Polly Peck, and Amber Day.

One of his notable contributions was exposing the fraud committed by Robert Maxwell, particularly concerning Maxwell Communication Corporation. His insights and actions in this regard highlighted his expertise in forensic accounting and his commitment to market transparency.

Gambling Ventures

Beyond the stock market, Cawkwell is an avid gambler, engaging in activities ranging from horse racing to sports betting. He has been active on betting exchanges like Betfair, where he placed wagers on various sporting events. In 2014, reports indicated that he made £150,000 in a single week through sports betting, showcasing his analytical skills and risk-taking propensity.

However, his gambling ventures have not been without challenges. In 2012, he reportedly lost £150,000 due to the collapse of the spread betting company WorldSpreads, which went into administration after a significant shortfall in clients' accounts was discovered. Additionally, he has had disputes with betting firms over the settlement of wagers, reflecting the complexities and risks inherent in gambling activities.

Public Persona and Writings

Cawkwell has authored several books sharing his insights into the financial markets and his experiences with short selling. His publications include "Profit of the Plunge: How to Win Short Selling" (1995), "Bear Essentials: The Secret of Forensic Accounting and Profitable Trading" (2003), and "Evils Good: Book of Boasts and Other Investments" (2012). These works offer readers a glimpse into his methodologies and the rationale behind his investment strategies.

Known for his candid and sometimes controversial opinions, Cawkwell has been a regular contributor to financial discussions, providing commentary on market trends and individual companies. His insights are valued for their depth of analysis and his willingness to challenge prevailing market sentiments.

Conclusion

Simon Cawkwell's career as a gambler and financial market participant underscores his analytical acumen and his readiness to engage in high-risk, high-reward ventures. His activities in short selling have had a notable impact on the companies he targeted and the broader market, while his gambling endeavors reflect a consistent application of risk assessment and strategic decision-making. Despite facing challenges and controversies, Cawkwell remains a significant figure in both the financial and gambling spheres, with a legacy characterized by boldness and a deep understanding of market dynamics.

For a more personal insight into Simon Cawkwell's perspectives on trading, investing, and gambling, you might find the following interview enlightening: