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

13 min read

04 June 2015

A sport career can be lucrative, but can also leave individuals floundering once they're past the peak years. Real Business takes a look at those who ventured into the world of business – the shrewd successes and those who scored own goals.

While many athletes are getting better at planning for their post-sport success – Dame Kelly Holmes established an initiative partnering up retired sportspeople with underprivileged young people – others find it difficult to adjust to a different life to the one they had already been leading. 

Manchester United’s former defender Rio Ferdinand has invested in a range of interests off the pitch – including an Italian restaurant called Rosso in Manchester and #5 magazine – setting him up well for when he retired recently at the age of 36. 

Not everyone has been quite so sensible in taking a leaf out of the centre back’s book – and there have been many times people have wondered just why so many sportspeople wind up in financial difficulty after such successful careers. Some of sport’s biggest names became infamous for all the wrong reasons after their playing wound down. Here we’ve compiled some of those, along some of the best.

Five of the best:

(1) Francis Lee

Many sportsmen – particularly footballers – make headlines for quickly squandering their fortunes, as you’ll soon see below. Francis Lee, however, was not one of them. The former footballer was Manchester City’s record signing at the time, when they agreed to a fee of £60,000 in 1967. He turned out to be well worth the money – scoring what turned out to be the winning goal to collect the First Division title in a game against Newcastle. Lee then went on to be the club’s top scorer for five seasons and spearheaded City’s golden era.

In terms of business nous, he wasn’t too shabby there either – running a successful toilet roll company after retiring from football, which turned him into a millionaire. When he was a teenager playing for Bolton Wanderers, Lee topped up his earnings by driving an old brewery lorry to collect wastepaper. 

Having spotted a market for soft toilet tissue, Lee injected his footballer income into his business called FH Lee. It also once employed comedian Peter Kay. He sold the company in 1984 for £8.35m.

While his stint as City’s chairman wasn’t so successful, Lee still sold the shares he had bought for £3m for a tidy £6m.


(2) Maria Sharapova

She may have crashed out of the French Open to Lucie Safarova, but Maria Sharapova is still one of the most successful tennis players of recent times and is currently the second seed. Ranked by Forbes as the world’s top-paid female athlete, it’s clear she has an eye for business too – despite Serena Williams having raked in nearly twice the career prize money, Sharapova’s endorsement deals cemented her status as the highest-paid sportswoman for the tenth year running in 2014. 

She invested $500,000 in her own global business – Sugarpova sweets – which launched in the UK in 2013. In Sharapova’s first year of business, she made more than a 120 per cent return on her initial investment, and was looking to double it for year two. She also took a stake – part cash, part sweat equity – in skincare company Supergoop to promote sunscreen and anti-ageing products. 

“Business and sport are both very competitive worlds, and I want to be the best in both,” she said.


(3) Tim Horton

Nowadays, when people hear the name Tim Horton most think of doughnuts and coffee, such was the former ice hockey player’s business success. 

The Canadian’s playing career was impressive though – he joined the Toronto Maple Leafs and soon garnered a reputation as one of the strongest in the game, winning four Stanley Cups and named in an NHL First Team All-Star three times. 

After a long sporting career, he founded the first Tim Hortons restaurant in 1964 with Jim Charade, which soon turned into a multi-million dollar franchise – eventually overtaking McDonald’s as Canada’s largest food service operator. 

Horton died aged just 44 in 1974, but his business legacy lives on – in August 2014 Burger King purchased Tim Hortons for $11.4bn.


(4) George Foreman

Another former sportsman whose name has taken on a different brand all of its own is, of course, George Foreman. Being known by many for nifty cooking equipment rather than being a two-time World Heavyweight Champion and Olympic gold medallist takes some doing, but the boxer’s entrepreneurial skills weren’t to be sniffed at. 

He teamed up with Russell Hobbs as a spokesman and had some say in the design of his self-titled grill, which went on to sell over 100m units worldwide. Foreman later sold the naming rights to the grill for $138m in 1999.


(5) Greg Norman

The golfer spent 331 weeks ranked as world number one throughout the 1980s and 1990s and has won over 85 international tournaments across his career. The Australian was nicknamed “The Great White Shark” in part due to his aggressive style of play, and his renowned drive stood him in good stead when he launched an entrepreneurial career. 

Norman’s knack was focusing on uniting business and sport, which seems a more reliable route to success. Similarly, renowned South Korean figure skater Yuna Kim launched her own sports management company in 2010, in a savvy move. Norman established Great White Shark Enterprises – a multi-national corporation spanning the US and Australia – focusing on golf course design and expanding to incorporate real estate, investment and even a winery. His business ventures reportedly ranked in $300m in revenues for 2014. If that wasn’t enough, he recently launched a $75m investment fund for small businesses.

Read on to find out who failed in their business efforts.

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.