Simon Leaf was sitting in the doctor’s office next to a footballer receiving news that would change the player’s life. The footballer knew something wasn’t quite right and medical tests had been ordered. This was not long after Fabrice Muamba had been saved by the speed of paramedics after having a cardiac arrest on the pitch at White Hart Lane, Leaf recalls, so tensions were heightened.
As the player’s lawyer, Leaf was asked to attend when the worst was confirmed and the consultant revealed the player had hypertrophic cardiomyopathy – the same condition as Muamba, where the heart muscles thicken and blood is pumped less efficiently.
“To get the results with him, to talk him through his options, to try to guide him through that process was a truly humbling experience,” Leaf says. “Advising on if they were to continue to take that risk, what that looks like in terms of the support available to him from clubs and his international team. Making sure all those procedures are followed to ensure his safety can be preserved as far as possible.
“In the work we do generally the best or worst that can happen is someone makes some money and someone loses some money. This is somebody’s life and his family’s livelihood at stake. You’re involved in helping to make the most difficult decisions. It’s very different from your ordinary day job.”
That, it transpires as Leaf peels back the curtain on his job, is an understatement. From working with Saudi royalty to the parents of academy players, he discloses what it is like to be a sports lawyer.
The 39-year-old points out that sports law wasn’t a major field when he started. Now, particularly in football, legal disputes provide fans with the drama they crave between matches.
It is woven so intricately into the game’s fabric that Manchester City fans once unfurled a “Pannick on the streets of London” banner in support of Lord Pannick, the lawyer defending the club against the Premier League’s 130-plus charges, and supporters have asked Nick De Marco, whose clients include Newcastle United and Leicester City, for selfies.
Leaf recounts all-nighters. “That may be trying to get a deal done in a large boardroom but often it’s not as glamorous as that. Typically, it’s late-night Zoom calls, passing drafts between lawyers. It can get heated from time to time.”
It is not, however, all about mega-money deals (one he worked on was worth more than £1bn). Leaf’s pro bono work includes advising academy teenagers asked to sign long-term contracts. League rules allow pre-scholarship contracts to be offered to 13-year-olds. Players are not permitted to be represented by agents at that age.
“There are a lot of good people in sport, but there are a lot of sharks looking to take advantage of families who often aren’t experienced as to how the industry works,” Leaf says. “At that stage, the clubs hold all the power. You’ll get a situation where clubs are getting parents and young boys to sign documents that commit them to the club for the next three or four years, sometimes even longer, without any legal advice.”
His previous firm launched a helpline for women in football who experienced discrimination to seek free advice. “Unfortunately, a week wouldn’t go by where we wouldn’t get a call for help,” Leaf says. “This was people from across the footballing world, from the boardroom to the boot room.”
Leaf “fell into law by accident”. He was a promising referee while studying business management at the University of Cambridge. “I was earmarked alongside the likes of Michael Oliver coming through the ranks. Most people were out partying every night and I was getting ready for Eastbourne away.”
Securing sponsorship from BLP for a law conversion course enabled him to continue refereeing. But when a knee injury ended that career, another began in sports law.
As a trainee, he worked on real estate for the Football Association’s St George’s Park build, intellectual property for London 2012 and some of the first “receivables financing” deals at football clubs. If a club sells a player for £10m but is paid the money over three years, a lender gives the club £9m upfront and receives the full amount over three years. It is how many deals are financed.
Leaf became head of sport at Mishcon de Reya, before recently setting up Three Points Law with Tom Murray, focusing on the intersection of sport and technology. “Almost every deal we do now has a tech or intellectual property or data angle to it. Be it a player transfer or the big sponsorship and broadcasting deals.”
Marcus Rashford and one of the technology companies that support video assistant referees are clients. The bulk of the work for that tech firm was preparing bids and negotiating contracts but it also involves analysing legal risks. In 2020 Hawk-Eye failed to award Sheffield United a goal against Aston Villa after the ball crossed the line. The point kept Villa in the Premier League. “That’s exactly the kind of issues we’re looking at when we’re acting for these vendors. Where does the liability sit? Can some of these risks be insured against?”
Players are increasingly using data in contract negotiations. “Athletes are actively looking at monetising their own data,” Leaf says. “We advise other sports on whether you can commercialise live heart-rate data. Seeing if there’s a way to bring that to the spectator so you can truly see the pressure these athletes are under.”