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Mister Loophole

Mister Loophole

Criminal Defence Lawyer Nick Freeman (aka ‘Mr Loophole’) writes exclusively for The Cheshire Magazine 


I was 12 years old when I watched Tony Jacklin clinch the 1969 Open at the Royal Lytham & St Anne’s Golf Club with my late father, and my best friend Peter. As a young boy already incubating his own passion for the sport, it was an incredible experience.

When Jacklin walked the final hole, I knew in that moment what I wanted to do with my life. I wanted to be him. And with youthful naivety and boyish self-belief I actually - thought I might succeed too. Part cringing, part chuckling now, I remember how, as a boy, I told myself I had the right credentials.

After all, I told myself, I was captain of the first X11 football, hockey and cricket teams, and had been a vigorous judo enthusiast. (the attraction of which paled once I was moved from boys to seniors and got thrown around like a lump of lard)

But it was golf I loved the most. There was something about having to master physical technique whilst coping with immense mental pressure which was hugely appealing to my competitive spirit.

Indeed by the time Jacklin had potted the US Open in 1970, I told myself I might even be catching up. At the age of 12 I’d already won the Henderson trophy (a competition for all Nottinghamshire golfers under 25 off a handicap of 24! ). Within four years, I was representing my home turf of Nottinghamshire, becoming junior county champion 12 months later. I was also junior county captain. In my teenage mind, I was on my way.

My late father, Keith, himself a keen one handicap golfer who’d played for Nottinghamshire’s first county team, understood how much I wanted to turn pro. But I’m grateful that dad also recognised the Herculean challenge of embarking on such a path: too many truly talented amateurs had failed to secure their card. What’s more - so he wryly pointed out - the prize money hardly compared with the riches to be gleaned through a successful career in law.

So instead, dad encouraged me to get a degree, qualify as a lawyer and then revisit my golfing ambition once I’d also secured a professional label. ‘If you qualify as a lawyer’, he told me, ‘you’ll always earn a living.’ It was the best thing he could have ever done for me.

Though, once I qualified he did dangle a carrot… of sorts.

Back in 1981, a newly qualified lawyer could expect to earn £5,000 a year. ‘If you can’t get a job which pays double,’ Dad told me with an impish smile ‘then I’ll sponsor you to play golf for two years and see how you go’.

Did I take the path of least resistance in order to cash in on his offer? I`m afraid not. I`m one of those dreadful people who have an insatiable hunger to win (great for court, not so great when you’re arguing over who left the fridge door open).


What’s more, I`d already been offered a job with a large commercial firm. Though that all changed when was I entered into and won an advocacy competition. As I stood there arguing my point I thought – and apologies for a bit of a theme here – this is what I want to do with my life. I wanted to be a criminal defence lawyer.

Those boyhood fantasies about becoming the next Tony Jacklin were junked quicker than you could say ‘not guilty’. I never took my father up on his kind offer. Instead I pursued my new-found love of criminal law by taking a position prosecuting for Greater Manchester Police (GMP).

Nearly four decades later do I regret becoming an officer of the court rather than an officer of the course?

Well, there are – albeit after a few beers in the club house – a few maudlin moments when I reflect what might have happened had I had a stab at a golfing career. But in truth I`m sure I never really had the talent.

Anyway, as the late John Lennon so wisely remarked, life happens when you`re busy making other plans.

Meanwhile, after spending two years with GMP I left in 1983, to join a prestigious firm of criminal lawyers in Manchester. Yet, ironically, as I climbed the legal ladder much of my life continued to revolve around world class sportsmen.

Not, alas, as a teammate, but as their brief, since countless footballers, snooker players, boxers, cricketers, golfers and more formed a large chunk of my client base. Ruefully I’d think about what it must be like to be that good at sport. Instead, after representing most of the players at Old Trafford, I had to content myself with being described as Manchester United`s best defender.

But in the process I also acquired another nick name – Mr Loophole. It was bequeathed by a journalist to describe the way I marshalled obscure legal technicalities to secure courtroom success. I didn’t like it – Mr Loophole suggested something underhand or dodgy and I’m neither (although I went onto trade mark it because I didn’t wants anyone else using it on the back of my reputation).

Anyway, if I’m really honest, I was a bit miffed at being made to sound like a second-hand car salesman (it didn’t escape my notice that legendary QC George Carmen was nicknamed the Great Defender). But over the years I’ve come to appreciate its benefits and so we rub along nicely.

Certainly, working in criminal law is a world away from the niceties of the golf course where gentlemanly argument is diverted with a waspish put down and the thwack of a well-aimed shot.

In court there’s the ruthlessness of unapologetic advocacy. Of slowly dismantling the testimony of a prosecution witness while summoning obscure details of the law – and it is law, not loopholes – to win the case.

Anyway, through the legal aid work – which ran parallel to my private specialism in road traffic law - there was the sheer excitement of mixing with the villains and bank robbers who came to me as their public defender.

But whether it was representing a petty thief or a premier soccer star, I applied myself with equal enthusiasm. Like the best sportsmen, to be top of your game in criminal law you fight to win. And like all good sportsmen, I never took my eye off the ball or failed to find ways to seize an advantage – through knowledge, advocacy and sheer focus

It is that so called ‘loophole’ knowledge which has enabled me to drill into the darkest corners of the statute to reveal police or prosecution incompetence.

And it has provided some of what have been described as my most ‘notorious’ legal arguments. From defending Sir Alex Ferguson against a charge of driving on the hard shoulder of a motorway by arguing that the Manchester United manager had had an upset stomach. To winning a successful appeal against conviction for speeding for David Beckham by arguing the then England captain was trying to escape the pursuit of a paparazzo and was fearful of his life.

However there have been other dividends in not pursuing a sporting career.

In short, I`m a terrible traveller. I get car sick even thinking about taking a lift with someone else. I have to drive everywhere and won`t go near airports or railways stations. The international peripatetic existence of the professional sports star would have been an absolute non-starter.

In contrast, pursuing a career in law meant I could put down roots here. In my beloved Cheshire.

Indeed, when I decided to establish my own practice, Freeman and Co, after 16 years with a city centre firm it crossed my mind to open in Knutsford. I adore the town with its village air, unaffected architectural quaintness and studded gentility.


But I discovered it was no more expensive to set up in central Manchester. I also feared that I might be regarded as provincial. Though, what I’ve since learnt is that if people want your services then they will find a way to access you (these days, something easily achieved by a consultation with Google or a shout out on Twitter).

It’s why I find the concept of the Northern Powerhouse so utterly meaningless. Of course, we need more investment in the infrastructure of the region. But the paradigm that labelling an area will somehow create a concept is risible. The brand should follow the work – not the other way around.

As my own practice grew I did consider opening up another office in London – especially since so much of my work was and still is rooted in the South East. But it would have absorbed too much time and energy.

But there have been other advantages in working from offices in Manchester rather than anywhere else. I can draw a line of demarcation between the buzz of our busy law practice and the tranquillity of my Cheshire home.

And tranquillity is something I prize – another reason I enjoy being out on the golf course, especially when I play at Delamere, a magical oasis unlike any other.

In fact, after marrying my first wife in 1991 finding somewhere to live that offered unrivalled peace and serenity was a key factor in choosing where to buy. I knew I’d nailed it, when I first looked at the property in Mere that, 27 years after first setting eyes on it, is still my home today later.

Although I liked the house for its cosy, compact design I was – and still am - absolutely poleaxed by the view. The trees were a conspiracy of browns and greens while sunlight sparkled across the expanse of water. What`s more, you can see the mere from every room of the house.

My then wife wasn’t as sure – we still had other properties to see. So, I turned to her and said ‘tell you what, darling. I’m buying this and moving here. If you want to join me, you’ll be very welcome.’ It was one of the best decisions I’ve ever made.

And there are added benefits in the location too. There are some lovely local pubs and restaurants nearby such as the Church Inn at Mobberley. Above all, I have Tatton Park on my door step. When I’m not working away I start each day with a 10 km walk through its magnificent acres with my Staffie, George. I turn off the phone, and we plunge deep into the woods and fields. There are days when I literally feel like I’m on safari as we plot new, uncovered tracks through the parkland.

Representing so many sportsmen does, I admit, remind me of my once yearned for dream – or rather pipe dream - of becoming a professional golfer.


No more than when I have the opportunity to play alongside any of them. Such as the two charity matches I took part in with Colin Montgomerie (whose conviction for speeding I got overturned after finding the police speed gun operator had also trained the device on joggers and dogs!).

Or after successfully defending Ronnie O’Suillivan by arguing the snooker superstar’s medication for depression had been the reason for his failure to produce a urine sample when suspected of drink driving. To celebrate Ronnie and I enjoyed a leisurely game of golf at Coombe Hill in Kingston Upon Thames where I finished Birdie Birdie to beat him on the last (having been persuaded to give him ten shots).

Half a century after first nursing hopes of becoming a professional golfer, it`s fair to say the sport endures as a critical component of my life – and therefore my work.

Out on the course I find sanctuary for a frazzled mind, freighted with a welcome but heavy case load. My phone is off, my thoughts focused. I play to win. Not unlike the way I perform in court (although when I leave the 18th I still think of the shots I left out there).

Achieving more than I could have ever imagined in my legal career has, of course, been consolation for not pursuing a golf career. Winning in court is almost – almost - as satisfying as hitting an ace.

Anyway, compared to Mr Hole in One, Mr Loophole is so much easier to say.

I`m sure Tony Jacklin would agree.

The Art of The Loophole by Nick Freeman is published by Hodder and Stoughton

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