Birthdate: 7th of May, 1936
Date of Death: 18th of May, 2024
Upon his final public appearance after many prosperous years in business and wealth accumulation, which ended abruptly owing to bankruptcy, Sir Anthony O’Reilly expressed his thoughts on success and failure to an auditorium in Dublin. He said, “Both victories and defeats are a part of life, and if you are unaware of how to handle defeat, you truly do not know how to live.”
These statements were indeed insightful. O’Reilly, who passed away at the age of 88 in Dublin, was a winner of immense magnitude more often than not. He was a captivating storyteller with casual appeal. He had a career that seemed larger than life. But, as fate would have it, he ended up bankrupt and in financial ruin.
Reflecting upon his situation, a company director who was well-acquainted with him, commented, “ Sir O’Reilly was habituated to being successful and being in a favourable spotlight. It must have been a herculean task and possibly an eventual embarrassment.”
Up until the year he exhausted his credit in 2015, the original business sensation of Ireland lived a life that seemed akin to myth.
Having earned his reputation as a celebrated Ireland rugby player and record-breaking scorer for the Lions, O’Reilly engineered a successful transition to becoming one of the most acclaimed – and terrifying – business executives of his time, having flourishing ventures globally. He had an iron hand over his business competitors, and his newspaper’s electoral position was indispensable. He approached and was sought after by political figures himself.
Ushering him from the muddied rugby fields of Dublin to luxurious company board meetings in the US was his appealing good looks, swift sense of humour and high-spirited zeal.
In addition to managing the Heinz brand of ketchup and baked beans in the US, he simultaneously ventured to render the Independent newspaper globally accessible from Ireland. He travelled across the Atlantic biweekly from his base in Pittsburgh with Heinz to administer several interests in Ireland. His illustrious career in Ireland covered the reign of nine taoisigh, stretching from the 1960s to the 2000s, starting during Seán Lemass’s term to that of Brian Cowen.
O’Reilly, a prominent figure in the media industry and well-connected business leader, garnered significant influence due to his associations with wealthy celebrities and authority figures. His lengthy stint as the head of Independent News & Media (INM), however, came to an abrupt end on his 73rd birthday in 2009. His bitter business dispute with Denis O’Brien led to his eventual expulsion.
It’s worth noting that O’Brien, recognized as the emerging mastermind in deals, outpaced O’Reilly’s alliance in 1995 to win State’s secondary mobile-phone license. O’Brien amassed his initial wealth through this license, albeit the award attracted a hefty backlash from the Moriarty tribunal. O’Brien consistently denied the tribunal’s claims that he had bribed Michael Lowry, the minister deemed responsible for enabling him to triumph in the 1995 mobile phone license competition for Esat Digifone; O’Brien’s company.
In 2001, O’Reilly bested O’Brien during the acquisition fight for Eircom. O’Reilly presented a €2.9 billion proposal for the previously government-owned telephone company, a bid supported by Goldman Sachs and renowned billionaire investor George Soros. Legislation was altered to facilitate O’Reilly’s transaction, amending tax laws to benefit the worker share ownership trust in Eircom that was union-supported, and would see a rise in its ownership through his proposal. This tax amendment, requested by the trust, was incorporated when then finance minister Charlie McCreevy was cautioned that O’Reilly’s proposal was at risk of collapse if such amendments were not implemented.
The struggle for INM started in 2006 when O’Brien, who had criticised the news group’s reportage of his dealings, acquired a minor share. This incited a turbulent conflict that escalated into an intense corporate battle. O’Brien continually increased his ownership ratio. As the tension escalated, harsh exchanges were thrown from both sides. INM labelled O’Brien a “rebel” investor, while he interrogated O’Reilly’s administration, questioning his strategic decisions and governance methods. One INM insider described it as a “battle on all fronts.”
Ultimately, the rebel emerged victorious in the battle for INM, positioning his own trusted executives at the helm of the enterprise. Even so, O’Reilly’s immediate successor and son, Gavin, had a falling out with O’Brien and subsequently departed. However, for O’Brien, his supremacy over INM was a hollow triumph. Similar to O’Reilly, he experienced a substantial financial loss when the company’s stocks plunged due to massive corporate debts and the financial downturn following the banking crash. Presently, INM is under the ownership of Mediahuis, a Belgian company.
These devastating events came upon O’Reilly at a point in his life when he could’ve been relishing his retirement from the strenuous pressures of corporate life. Not only did his personal wealth shrink significantly due to the falling shares, but also the cessation of INM’s yearly dividends, which had previously generated over €31 million for him in 2007 alone, hampered his capacity to handle his immense personal debts which he continued to shoulder even in his 80s.
In the past, O’Reilly, as well as his supporters, had encountered costly failures. Atlantic Resources, his energy exploration company from the 1980s, saw investors lose heavily due to useless drilling ventures off the Irish coast, which discovered nothing more than a small amount of oil. Nevertheless, these setbacks had barely dented his wealth on any significant level.
Even though numerous Irish business magnates amassed considerable wealth during the Celtic Tiger era, O’Reilly had been accumulating his wealth since the time when the underdeveloped Irish economy was still a synonym for paralysis. BusinessWeek magazine in the US cited that his total earnings in the 1990s spanned six years and totalled nearly $183 million.
He enjoyed the distinction of being perceived as Ireland’s wealthiest individual and its inaugural billionaire for a considerable period, flaunting his wealth in kind.
O’Reilly possessed a collection of three homes in Ireland – a Dublin property in Fitzwilliam Square, a 750-acre country estate in County Kildare’s Castlemartin, and a coastal holiday home in County Cork’s Glandore. His international assets included a beachside retreat in the Bahamas, a chateau in Deauville, France, and a lavish Tudor-style dwelling in the suburbs of Pittsburgh. His art collection was equally impressive, holding works from notable artists such as Picasso, Sir William Orpen, Roderic O’Conor, Louis le Brocquy, and Jack B Yeats, along with a Monet that he spent more than $24 million on.
However, O’Reilly’s fortunes took a significant downturn with the collapse of Waterford Wedgwood, which drained vast amounts of his capital before entering receivership in 2009. O’Reilly and his brother-in-law, Peter Goulandris, lost hundreds of millions of euros investing in the ill-fated luxury goods firm, a critical bet that led him to precarious circumstances as problems at INM escalated.
When his financial struggles reached their peak, O’Reilly was declared bankrupt, with debts amounting to around €150 million, following a €22.6 million debt judgement against him by the State-owned Allied Irish Banks in his 2015 Bahamian bankruptcy. Many of his treasured long-held assets were sold off. U.S tycoon John Malone purchased the Castlemartin estate which O’Reilly had emotionally referred to as his “spiritual home” and where he had given his parents a final resting place in a private graveyard by a medieval church that he had renovated.
For a man so accustomed to public adoration and success, his fall from grace was equally as public. Following his exit from bankruptcy in December 2023, one colleague mentioned how painful this downfall likely was for a man who had contributed positively to Ireland.
It would have been hard to predict such a fall from grace when O’Reilly was in his prime, receiving birthday wishes via video from U.S president Ronald Reagan and even playing tennis with his successor, George Bush Senior, at the White House.
Anthony John Francis O’Reilly had an impressive advisory board at INM which included globally recognised figures such as past editor of the Washington Post, Ben Bradlee, former James Bond actor Seán Connery, ex-Tory chancellor Ken Clarke, and prior prime minister of Canada, Brian Mulroney. His personal circle of acquaintances included the likes of past U.S. president Bill Clinton, Senator Ted Kennedy and South Africa’s leader Nelson Mandela.
In 1976, O’Reilly capitalised on his global sway to set up the Ireland Fund of the US, the precursor to the Ireland Funds. This initiative successfully gathered over $600 million for peace and reconciliation projects in both Northern and Southern Ireland. This fund proved instrumental during Ireland’s Troubles, aiding Irish governments in their endeavour to secure backing from Washington for constitutional nationalism, whilst also crippling IRA fundraising in the US.
O’Reilly’s dedication to the Ireland Funds was acknowledged by Queen Elizabeth, who knighted him in 2001 for his significant contribution to Northern Ireland. This remarkable attainment marked the first ever full knighthood awarded to an Irish individual. The government’s approval was required before acceptance, leading him to adopt the title of Sir Anthony thereafter.
Born on May 7th, 1936, in Dublin to Aileen O’Connor and Jack O’Reilly, a customs officer and separated father of four, Anthony spent his childhood in Griffith Avenue, Dublin, and received catholic education at Belvedere College.
Unaware of his half-brothers and sisters until his teens, he learnt about them at school. The period’s societal norms made the subject of illegitimacy a sensitive one, with the constitutional prohibition of divorce still in place. After learning their secret, many years elapsed before he confessed to his parents. They tied the knot in 1974 upon the demise of his father’s former wife.
O’Reilly was well-liked at school and had an obvious talent for athletics, but eventually chose to focus on rugby. After completing his schooling at Belvedere, he studied law at University College Dublin whilst simultaneously serving as an apprentice to a solicitor.
Rugby remained his main interest and he had an extraordinary first season at a senior level, which ended with his selection for the Lions’ 1955 South Africa tour. Prior to this event, he participated in all of Ireland’s international matches.
O’Reilly quickly distinguished himself in the world of sport, earning a try in his inaugural Lions test game and becoming the tour’s leading scorer. His impressive performance continued as the Lions toured Australia and New Zealand in 1959. He set a record with the Lions for the most tries, at 37. He also earned 29 caps for Ireland, with his final international game taking place in 1970, after a seven-year hiatus. Tracked to Annabel’s nightclub in London by team selectors, he showed up for training the next day in a chauffeur-driven Bentley.
In 1958, O’Reilly earned his solicitor credentials but never followed the legal pathway. Instead, he built his career as a management consultant in Leicester, then moved to Cork two years later, taking up the role of the assistant chairman of a general builder’s merchant business that also dealt in fertiliser, seed, and oil.
In his early days, he was often referred to as the “Golden Boy”. He achieved the distinction of being the youngest head of a State-sponsored organisation during the Lemass era, a period marked by Ireland breaking free from decades-long protectionism.
As Ireland slowly let go of its insular economic approach, O’Reilly was part of the new generation of entrepreneurs who identified potential in the changing environment. On par with the likes of Ryanair founder Tony Ryan and packaging tycoon Michael Smurfit, O’Reilly, born in 1936, had a transformative effect on Irish trade. He visualised international business as his arena, and built a global career long before Ireland’s remarkable growth in the Internet age as one of the most globalised nations.
Being a sports legend granted him celebrity status. His 1962 matrimony to Susan Cameron, the Australian heiress of a prosperous mining executive and the mother of his six children, was considered cinematic by the Evening Mail. One associate mentioned, “One thing that was noticeable was his ability to connect on a personal level. Regardless of who he was interacting with, he genuinely seemed interested in you as an individual.”
In 1962, the Irish Dairy Board, Bord Báinne, saw him ascend to the role of General Manager. His efforts towards modernisation greatly contributed to the dairy industry, with the successful launch of Kerrygold butter brand in Britain being a personal triumph. Its still prominent presence today is a testament to his success. He further delved into the marketing of Kerrygold, which became the focus of his PhD thesis, awarded by Bradford University in 1980.
In 1966, at the behest of then Taoiseach Jack Lynch, O’Reilly took the reins of the Irish Sugar Company. One of his primary responsibilities was to rectify the considerable losses the company’s subsidiary, Erin Foods, had incurred. Despite an attempted merger with Heinz UK, the combined entity, Heinz-Erin failed to flourish. In 1969, he stepped away to take on the role of Managing Director of Heinz in Britain, progressing to Senior Vice-President by 1971. By 1979 he held the position of Chief Executive.
Criticism accompanied O’Reilly during his lengthy tenure at Heinz, however, his transformative input is undeniable. When he assumed control the business had a value of $900 million, by his retirement in 2000 as Chairman, it was worth $23 billion. In 1987 he was appointed as the first Chairman outside the Heinz family and held the dual role of chief executive until 1998.
His golden era within Heinz was the 1980s. However, in the following decade, he faced increased scrutiny over his pay and managerial approach. Forbes cited him as the fourth highest earning CEO in America, but commented that his income and ego outweighed his achievements. BusinessWeek also criticised him with allegations in a prominent feature, suggesting an oversized influence on the board, a claim similar to those made against Irish companies INM and Waterford. Elaborate corporate expenses, alongside 2,500 job cuts, only magnified criticisms.
O’Reilly’s loyalty to Heinz was generously rewarded. Yet ironically, he confessed that Heinz’s iconic ketchup was not his preference. His attention was captivated more by newspapers and their diversity, considering them “more than you can get out of baked beans”.
In an agreement with Heinz, he kept a significant presence in the Irish business sector. Even in his 30s, he was a driving force behind the Fitzwilton conglomerate, previously one of the top three companies in Ireland, employing 4,400 individuals. Fitzwilton, however, underwent serious challenges. The banks stepped in to secure their assets in 1975, and within two years, he had brought the company back to financial stability. Regardless, the event left a dent in his reputation, and the public questionings of his judgement by banks left him feeling wronged.
O’Reilly looked back on Fitzwilton’s acquisition of the historic Waterford Wedgwood in 1990 as something of a personal victory. This turned out to be a significant decision which gradually drained increasing amounts of money as his dream of establishing an Irish luxury industry for the 21st century dwindled due to substantial trading losses and overwhelming debts.
Following his 1990 separation from Susan O’Reilly, he entered his second marriage with Chryss Goulandris, an heiress to an immense Greek shipping wealth and the holder of significant bloodstock stakes. Raised in New York with family homeownership on the prestigious Park Avenue, they wedded in the Bahamas in 1991. In a grand gesture, O’Reilly purchased Jackie Kennedy’s diamond engagement ring that was given by Aristotle Onassis for his second wife for a sum of $2.59 million from a Sotheby’s auction. Following his knighthood, Chryss went by the title, Lady O’Reilly.
In the long heyday at INM, which lasted a substantial period, the news industry was his most profitable investment. In 1973, at the age of just 36, he acquired control of the publisher of the Irish Independent, the Sunday Independent and the Evening Herald by borrowing slightly over £1 million. He used this to invest in a business that had been run by generations descending from William Martin Murphy, a notorious businessman involved in the 1913 Lockout.
Revitalising what had become outdated titles, O’Reilly fortified his position by purchasing the Sunday World tabloid and several of the strongest local weekly publications. Subsequently, he acquired an essential stake in the Sunday Tribune, a controversial decision which he justified as a protective move against Rupert Murdoch’s Sunday Times. The Tribune, a constant loss-bearing entity, ceased operations in 2011.
An intrigue-riddled but short-lived episode was the stake O’Reilly acquired in Independent’s long-standing adversary, the Irish Press publisher, merely months before its downfall in 1995. The Competition Authority condemned Independent’s investment in the consortium formed by Éamon de Valera as a manipulation of its predominant market standing.
Moreover, Independent co-published the Irish edition of the sensationalist Star, followed by the procurement of the Belfast Telegraph later on. A newspaper enthusiast, O’Reilly gained a reputation as a benevolent owner. However, his inadequate attention towards investing in editorial assets drew criticism. Irish profits buttressed international growth as the enterprise diversified with publications in nations including Australia, New Zealand, India, South Africa, and Britain. O’Reilly portrayed his loss-driving London Independent publications as his “business card” in the metropolitan city. According to O’Reilly’s authorised biographer, Ivan Fallon, the tally of the news dailies evolved from “three to 128”.
Yet, international tensions with O’Brien and increasing debt pressure on INM during that epoch led to the dissolution of the global stable. The London Independent editions were sold off for a token £1 to Alexander Lebedev, a billionaire from Russia and former KGB agent.
Owning media houses offered O’Reilly a closeness to authorities, which he greatly cherished. He revealed to Forbes in the 1980s, “I have a direct line to politicians as I possess 35 per cent of Ireland’s newspapers”. His stake in the market escalated over the years, and as a result, so did his interaction with global leaders.
An 1988 article in the New York Times underlined a high level of self-publicising in the Sunday Independent after an eight-page colour feature about O’Reilly with 17 photographs was released. The displayed images featured O’Reilly with several dignitaries, such as Henry Kissinger, Margaret Thatcher, Valéry Giscard d’Estaing, and Robert Mugabe. Another showed him disembarking from a corporate jet.
Despite being the crown jewel in the O’Reilly network, the eloquent Sunday Independent attracted attention for its consistent antagonism to the Northern Ireland peace process during the 1990s, as steps to quell the recurring violence were underway.
The infamous “Payback Time” editorial that featured on the front page of the Irish Independent right before the 1997 general election drew significant attention due to its clear backing of Fianna Fáil and harsh attack on the incumbent Fine Gael-led rainbow coalition. John Bruton, the then taoiseach heading the government, had fallen out of grace with O’Reilly due to a disagreement over television broadcasting policy. This policy was of particular interest to Independent, who owned stakes alongside American partners.
Bruton had been summoned to O’Reilly’s Glandore home one Sunday morning in summer 1996 to hear grievances related to the failure of his government in tackling unauthorised TV operators, causing harm to the legal businesses supported by O’Reilly. The situation had a heavy political undertone because the government was apprehensive that taking action against the illegal providers might lead to losing seats in the approaching election, a debate later examined by the Moriarty tribunal.
During a subsequent meeting with INM executives, Seán Donlon, an advisor to Bruton, was given a clear understanding of the group’s “antagonism” towards government parties if matters were not resolved in their favour. It was noted in an INM memo that the government might risk losing the company as allies.
Bruton explained to the tribunal that he understood the potential loss of INM as allies to imply negative press coverage, not a legal challenge. However, O’Reilly disagreed with this interpretation. He suggested that the potential estrangement of INM was hinting at a possible lawsuit concerning the TV issue and had nothing to do with editorial bias.
Although the atypical front-page editorial rose many eyebrows, O’Reilly maintained that he had no say in its creation or placement. In his own newspaper, Irish Independent, editor Vinnie Doyle stated that the editorial was not influenced by O’Reilly.
The 1997 election resulted in enough seats for the Fianna Fáil party to form a coalition government with the Progressive Democrats. Ray Burke, the foreign affairs minister, subsequently resigned from Dáil after it was revealed that he had received £30,000 from a businessman before the 1989 election.
Later, it was discovered that Burke had also received a comparable amount from Rennicks Ltd, a Fitzwilton subsidiary owned by O’Reilly, in that year. As the head of communications, he granted seven television broadcasting licences to Independent and its global associates.
In 2005, Fitzwilton filed a lawsuit to block public hearings on Burke’s payment from Rennicks, as ordered by the Mahon planning tribunal. Fitzwilton’s legal team stated, following a Supreme Court verdict prohibiting such hearings, that O’Reilly was unaware of the payment made “via Mr Burke” for Fianna Fail until a decade later.
Previously, O’Reilly had rejected overtures from both Fianna Fáil and Fine Gael to become politically active in Ireland. Notwithstanding, he remained staunchly non-partisan in US politics, though his media assets ensured that political figures were keenly attentive to his views. He detested the idea of businesses being beholden to politicians, declaring that business is autocratic and not democratic.
He cited Winston Churchill as his idol and source of motivation. According to O’Reilly’s interview with BBC, the British war leader was an egotistical and vain individual who was highly aware of his importance. He suggested that delf-belief is a crucial success component—you need to believe that you are at the heart of everything that happens.
Lady O’Reilly passed away in August 2023 at the age of 73. HIs children Cameron, Gavin, Tony Jr, Susie, Justine, and Caroline outlive him. Their mother, Susan O’Reilly, succumbed in 2014.