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No matter what anyone says about Tony O’Reilly’s motivations, he knew how to live a full life

O’Reilly and Bruce Springsteen embody a similar truth about the world - you can’t start a fire worrying about your little world falling apart

In somewhat morbid fashion, I have been thinking lately about what it means to live a full life. This was prompted by two events – seemingly unconnected – that struck Dublin over the weekend. First, the death of Sir Anthony O’Reilly on Saturday – a luminary of the transatlantic boardroom and a bastion of Irish business. And second, the arrival of Bruce Springsteen at Croke Park – a 74-year-old rock star in possession of a “striking vitality” (as The Irish Times critic Ed Power put it) that would look more at home on someone not yet middle-aged.

The two men – one a blue collar champion of small town Americana, and the other a standard bearer of the corporate world – share an unlikely philosophy.

“You win and you lose, and if you don’t know how to lose, you don’t know how to live,” said O’Reilly in his final ever public appearance at Belvedere Rugby Club in 2018. I was struck by the humility of the statement. Figures that loom as large as O’Reilly in the public consciousness – whose work and reputation take on otherworldly qualities – can feel distant, miles detached from day-to-day reality. But O’Reilly’s statement spoke to a very human instinct, and served as a welcome reminder that behind all the lofty notoriety there always exists a real person.

There is a mode of masculine insecurity – a muscly bravado – that struggles to admit loss or defeat; that sees failure as inherently effete. This attitude is straight from the Donald Trump playbook: in 2020 The Atlantic reported that Trump privately called marines who died at Belleau Wood “suckers” and fallen soldiers at the Aisne-Marne American cemetery “losers”. It is, in fact, a favourite word of the potential incumbent. In a now deleted tweet from 2013, the then soon-to-be president (ever the gentleman) commemorated the anniversary of 9/11 by offering “best wishes to all, even the haters and losers”. Meanwhile, at the 2005 Grammy Awards, when Kanye West won Best Rap Album of the year he goaded the audience: “Everybody wanted to know what I would do if I didn’t win,” he said, followed by a long pause, pregnant with all that bravado and insecurity. “I guess we’ll never know,” he concluded.


The humility of O’Reilly’s introspection at that moment stands in sharp relief to these self-appointed alphas of the zeitgeist. It was also a neat encapsulation of the vertiginous highs and lows of his career. At points he was among the most celebrated businessmen both sides of the Atlantic Ocean; he was Ireland’s first billionaire (a victory by some people’s metrics); a record-breaking scorer for the Lions; he was successful at Heinz and in the battle for Eircom. But his time leading Independent News & Media ended in tears over a row with Denis O’Brien; he eventually suffered total “financial implosion”. The obituary of the man in these pages summed it up: “By the end of it all he was broke and bankrupt. It was a drastic fall.”

Complicated characters are often quickly condemned: critics mistake their instinct for cynicism as analysis, they eschew generosity of spirit for dispassionate assessment, they dress up prejudice as fair-minded concern. But such a lack of charity is self-defeating. People exist in these murky areas – rough with smooth, success that is abetted only by failure, flashes of moral ambiguity. No matter what anyone thinks about the purity of O’Reilly’s motivations or the guilt of his associations (he rubbed shoulders with Henry Kissinger and Robert Mugabe, among others), contradictions are what make life interesting.

Meanwhile, in Croke Park on Sunday there were echoes of the O’Reilly philosophy. Springsteen was reportedly sprightly and gave an emotional tribute to Shane MacGowan (another complex character) with a Rainy Night in Soho. He was met – as Power describes – with an audience full of adoration and hero-worship. Springsteen is remarkable for his refusal to capitulate to the demands society makes on the older among us (his physical fitness and mental lucidity have long stood out).

But it is in the penultimate song of the set – and his greatest hit – where it is clear that O’Reilly and Springsteen understand a similar truth about the world. “You can’t start a fire worrying about your little world falling apart,” Springsteen defiantly sings on his 1984 track Dancing in The Dark. As a thesis statement it is no different from O’Reilly’s final public missive: “If you don’t know how to lose, you don’t know how to live.”

Both are descriptions of a disposition required for a life well lived. But more than that, they are an argument. O’Reilly’s acceptance of wins and losses, the wisdom that one cannot exist without the other, and his courage in the face of criticism (warranted and not) are to be celebrated. Springsteen’s refusal to slow down – and his realisation that without risk there is no chance at victory – is a philosophy that pertains as much to O’Reilly’s boardrooms as it does to Springsteen’s America. Ideological allies can emerge from the most unlikely of places.