The five best and worst sports stars who tried their hand at business

Five of the worst:

(1) Keith Gillespie

Dubbed the new George Best a big name to live up to if ever there was one when he broke into the Manchester United first time at the tender age of 17, Keith Gillespie ended up blowing over 7m. This wasn’t solely due to poor business sense, he also had a well-publicised gambling problem. He did though, run into the familiar tale of misguided investments.

These spanned properties to a poorly thought-out film scheme he became involved with in 2001 and didn’t give another thought to until he received a letter in 2007 laying out the tax implications of the film syndicate.

The missive from Hannah Thompson detailed that the tax liability due on the Film Partnership Profits was 436,000 spread out over ten years,” he said. All of which played a part in Gillespie being declared bankrupt in 2010.

(2) Sheryl Swoopes

The US basketball player had been hailed as the female Michael Jordan and was the first woman to have Nike name a shoe after her the Air Swoopes. Despite her sporting success, winning a cluster of titles and individual accolades, Swoopes began hitting the headlines for her financial issues off the court.

In another tale that stresses the importance of having secure, reliable advisers, Swoopes was guided by dodgy handlers blaming both agents and lawyers for her money issues. She also admitted her own poor financial management, with a string of bad investments and ended up declaring herself bankrupt in 2004, after owing her creditors around $750,000.

She has since dipped her toe back into the world of business now running a medical supply company in Houston called MVP Medical Supply Company, helping those in need of equipment.

(3) Joe Louis

The cultural icon is considered one of the greatest heavyweights of all time and was notable for cleaning up the sport’s reputation as an honest, agreeable fighter at a time when it was besmirched by gambling interests. Despite winning over $4.6m during his lucrative boxing career, Louis himself only received about $800,000 of that, with most going towards his handlers.

He invested in numerous businesses, banking on the currency his name carried trying everything from the Joe Louis restaurant to the Joe Louis Insurance Company to the Joe Louis Milk Company. Unfortunately, all of these failed and entrusting his finances to former manager Mike Jacobs proved a bad decision. His ongoing popularity served him well though fellow boxer Jack Dempsey served as honourary chairman of a fund to assist Louis when he fell on hard times.

(4) Robbie Keane, Jimmy Bullard, Gabby Agbonlahor and many others

Players including Irish striker Robbie Keane and Aston Villa’s Gabby Agbonlahor lost millions after a 30m investment scheme went bust in 2012. In what was reportedly the biggest fraud perpetrated on players in English football, a former player Michael McIndoe (whose playing career included Wolves and MK Dons) told others he had a miracle scheme that paid 20 per cent interest per month on investments he was making in gold, stocks and property. He was soon inundated with requests from players, before it unravelled that McIndoe was using a Ponzi scheme. Scotland Yard opened an investigation into the fraud.

(5) Curt Schilling

The former baseball pitcher helped lead the Philadelphia Phillies to the World Series in 1993, as well as winning World Series championships in 2001, 2004 and 2007 with the Arizona Diamondbacks and the Boston Red Sox. After retiring, he decided to try his luck in the business world, founding Green Monster Games later renamed 38 Studios, an entertainment company.

It released its first (and only) video game in 2012, which sold 1.2m copies in the first 90 days and received positive reviews. Schilling had received a $75m guaranteed loan from the Rhode Island’s Economic Development Corporation and moved the company there from Massachusetts, but the failure of the loan meant 38 Studios was shut down and all the staff laid off, with Schilling admitting he had been naive.

The state police, attorney general’s office and the FBI launched investigations, with the state of Rhode Island filing a lawsuit against Schilling, the director of the EDC and 38 other backers of the studios settling for $4.4m last year.

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