The Freshfields corporate veteran talks to Alex Aldridge about life in the buccaneering eighties, rugby in the office and facing his fourth recession

Freshfields Bruckhaus Deringer veteran dealmaker Barry O'Brien does a good line in 1980s war stories. All-nighters rounded off by pints of Guinness at Smithfield market pubs feature heavily. As do hostile takeover bids, many of them initiated by highly personal full-page newspaper ads. And then there were the rights issue prospectuses featuring the gratuitous pictures of bikini-clad women. "Looking back, I suppose it felt a bit like the Wild West – the rules on advertising and photographs were, of course, subsequently tightened," he reflects.

In the early part of the '80s, Freshfields was an elite, but conservative City law firm which focused on private client work and acting for longstanding client the Bank of England. O'Brien and a group of up-and-coming corporate partners – including Anthony Salz, Gavin Darlington and Alan Peck – changed all that.

"We saw the opportunities that Big Bang presented, in particular with the arrival of the US investment banks into London, and were determined to play a part in it," recalls O'Brien, 57. The shift to representing investment banks, which the Bank of England was responsible for regulating at the time, was said to be controversial within the firm, but O'Brien insists that it was done with the backing of the Freshfields old guard. "In fact, they'd be slapping us on the back as we walked into the partners' dining room after doing another big deal," he says.

Having developed relationships with the leading banks of the era – including SG Warburg, Morgan Grenfell and Hill Samuel – O'Brien and his contemporaries set about winning work from their corporate clients: "That was when we got the ICIs, the AstraZenecas and the Tescos of this world on board."

What stands out, above all, from those days for O'Brien is the closeness of the relationships he formed – in particular with his colleagues, or "band of brothers" as he refers to them. The association began when O'Brien, then a solicitor at Slaughter and May, got to know Freshfields trio Salz, Darlington and Peck while acting on the other side of banking deals and found a shared vision. A somewhat controversial move across the City ensued – back then moves between leading law firms were even rare at solicitor level. Two decades later it was these friendships – and others that O'Brien subsequently developed with the likes of Mark Rawlinson and Guy Morton – that would provide the support to see him through a conflict of interest case involving his role in Philip Green's aborted 2004 takeover of Marks & Spencer, which led to him receiving a £9,000 fine from the Law Society two years ago.

"Obviously that wasn't the most enjoyable time," reflects O'Brien. "But my enduring memory of it is of my colleagues closing ranks around me, then marching down to the tribunal surrounded by all the leading lights at the firm."

Given the length of time they have known each other, it's no surprise that the Freshfields senior brigade is close – so close, in fact, that each has their own nickname. O'Brien is 'Bazza', or B JOB (his initials). Stories abound of Bazza and the crew covering up CCTV cameras to play impromptu games of rugby in the Freshfields corridors, which during recent years have apparently given way to more sedate putting competitions.

If all this sounds rather clubby and public school, O'Brien's background is a reminder that there were meritocratic channels of entry into the City even in the 1970s. The son of a Cardiff docker and a mother who put a premium on education, O'Brien was one of six boys brought up in a modest house in the Welsh capital's Irish Catholic community. Having done well at St Illtyd's Catholic High School, he won a place to study law at UCL before going onto do articles at Slaughters.

O'Brien remains synonymous with the drive, pragmatism and personality that made Freshfields' corporate practice one of the best in the world, but the indoor golfing antics of O'Brien and co. do feel slightly out of step with the modern, international law firm that Freshfields has become. Although plenty of the firm's lawyers can be found at the Harrow pub opposite the firm's Fleet Street headquarters on a Friday evening, these days pro bono and other corporate social responsibility (CSR) activities have largely replaced pints as the medium through which up-and-coming associates get to know each other outside the office. Surely it can't be as much fun?

"There used to be more downtime," responds O'Brien diplomatically, who, for the record, is no stranger to CSR, acting as a governor at Haggerston Girls School in Hackney. He attributes the change to the advent of the internet, making document exchange instantaneous in a way that wasn't possible in the past, and cutting out the need for as much face-to-face interaction as there once was. "Which is why it's so important for people like me to put the fun back into it," he adds – hence the softball game and barbecue that he is hosting for his team at his house in Islington that evening.

Of course, it wasn't all fun-filled downtime in the old days. There were times when O'Brien and his colleagues worked hours that even the most hyperactive young deal lawyer would find extreme. The rescue of Lloyd's of London in the early '90s, which saw a group of 200 Freshfields lawyers work round the clock to save the stricken insurer, was one such period. O'Brien, who one colleague described as "the person I'd want by my side in a crisis more than any other", remembers working for a 17-week stretch without a single day off, followed soon after by a similar non-stop 13-week stint. Having helped prevent Lloyd's from falling over, he became the first lawyer to receive the Lloyd's Silver Medal since 1824. It was a proud moment, made even prouder by the fact that the last lawyer to get the award was firm founder James Freshfield.

O'Brien attributes much of his success to the support he has received from his wife, Sue, a nurse who he met at a Law Society rugby club disco when he was in his twenties. "Half of the job for Sue has been looking after the children; the other half has been looking after me," he quips. The eldest of those children has just secured a training contract at Slaughters. Does O'Brien worry about what the future may hold for her in a legal services market that some predict is on the cusp of major change?

"No," he responds. "I don't see a major shift in the way firms operate at the top end of the market, although there are obviously some changes going on – our paralegal compliment, for example, is substantially down on what it was as clients increasingly look to get that level of work outsourced wherever they can."

O'Brien has similarly forthright views on the economy, which he expects, from an M&A standpoint at least, to "come back again and come back sooner than people think". He bases this forecast on the previous four downturns he has been through: "What's happened each time is that some deal has come along and kickstarted the whole thing, and then all of a sudden we've found ourselves completely swamped."

As for the future for O'Brien himself, he seems pretty content in his role as head of Freshfields' corporate finance practice, keeping his legal skills sharp on the recent wave of restructurings that have been flowing into the firm, while passing on what he has learned to the next generation of hotshot lawyers. Having run for senior partner in 2005 – he reached the six-partner shortlist but decided to withdraw because of the continuing M&S saga – does he ever regret not having had the opportunity to do the top job?

"Would I have done it if I'd been elected? Of course. Do I have enormous frustration or resentment at the fact I didn't get it? No, because I'm having too much fun."

And with a quick handshake, O'Brien is off to play softball.

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Mark Rawlinson – Freshfield Bruckhaus Deringer
"How would I describe Barry? Certainly not as shy and retiring. He's got this Desperate Dan, jaw-strutting, never back-down style – and he's always looking to get on the front foot, which means the client always feels that he's on their side."

Philip Yates – Perella Weinberg
"Barry's a sports nut and he applies that same passion to his job, which is why so many clients love working with him. Fortunately, he's a much better lawyer than he is a golfer…or skier. He had the most spectacular fall in Beaver Creek, Colorado, earlier this year; there was blood all over the mountain for three days. But that's Barry, he throws himself into whatever he's doing."

Anthony Salz – Rothschild (former senior partner at Freshfields)
"Barry has always been a determined pursuer of his clients' interests and very good at it. The work he and others in his team did for Lloyd's was a particular example. The restructuring was not only fiendishly complicated, it also required considerable stamina and perseverance. "

Charles Randell – Slaughter and May
"I knew Barry when he was at Slaughter and May, and being a fair bit junior, I looked up to him. Subsequently I've encountered him on the other side of deals. As well as being a big character, he's a technically very strong and thoughtful lawyer."