In 1968, Desmond's business career began with
Citibank in Dublin, followed by Price Waterhouse in
Kabul, Afghanistan. In 1995, Desmond founded International Investment & Underwriting (IIU), a private equity firm and his primary investment vehicle. It is located in Ireland's
International Financial Services Centre (IFSC) at IFSC House and is regulated by the
Irish Financial Services Regulatory Authority. Companies that are controlled through IIU include
Daon, Inc. (a biometric enabling technology company). IIU Asset Strategies Limited is the hedge fund arm of the company, offering convertible bonds and equity funds. In 1997, together with business partners
John Magnier and
J.P. McManus, Desmond purchased the five-star Barbados resort
Sandy Lane Hotel. The hotel underwent a US$450 million renovation and was re-opened in 2001. Desmond purchased
London City Airport from
Mowlem for £23.5 million in 1995. The investment was considered a large risk as
London's Docklands was in
recession and the neighbouring
Canary Wharf development was in
receivership. The airport has since become one of the more profitable in the United Kingdom. Desmond sold London City Airport in October 2006 for a reported £750 million to a consortium consisting of insurer
AIG,
GE Capital and
Credit Suisse.
BETDAQ is the trading name of Global Betting Exchange, a betting exchange operator based in Ireland. It is the second largest betting exchange operator in the country. The company was founded in 2000 by Desmond and started trading in September 2001. Its headquarters are in the International Financial Services Centre in Dublin. Desmond sold BETDAQ to Ladbrokes for €30 million in 2013 and is a shareholder at the bookmaker as a result of the deal. In November 2021, Desmond bought BETDAQ back from the Entain group (owner of Ladbrokes Coral) for an "undisclosed sum". Desmond was a major shareholder in Irish food company
Greencore for several years. He sold his shares in 2006. In 2005, Desmond opened the Sporting Emporium, a Dublin-based private members gaming club. It was reported Desmond had invested €5.5 million in the venture. After being open for only seven months it faced closure. Desmond purchased 33.1% of Latvian
Rietumu Banka in 2005 for a reported €66 million. He invested in the bank as a result of being very impressed with its management team and capital structure. The investment in Rietumu initially looked a successful one with Desmond's holding at one stage being valued at €200 million. However, the subsequent economic downturn has reduced the value of Desmond's holding in the bank significantly. In August 2008, Desmond was offered the position of chairman of the Irish airline
Aer Lingus. Desmond turned down the offer citing prior commitments as a factor which would not allow him the sufficient time necessary to do the job. Former GPA chief operating officer and current Babcock & Brown Air chief executive Colm Barrington was subsequently named chairman of Aer Lingus. On 19 September 2018, it was announced that Desmond had increased his stake in Toronto mining company Mountain Province Diamonds to 28%. The company's sole asset is the Canadian
Gahcho Kue Diamond Mine Project. In September 2018, he secured planning permission to construct a 17,168 sq ft. palatial mansion on
Shrewsbury Road in the
D4 postal district of
Dublin. In gaining approval for the ambitious mansion plan, Desmond was also given permission to demolish the existing house, "Walford", the most expensive house ever sold in Ireland at €58 million in 2005.
Glackin report In 1991, a company law inspector, solicitor John Glackin, was appointed by the then Government to investigate complicated dealings involving Desmond and the purchase and sale of the former Johnston Mooney & O'Brien site in Ballsbridge, Dublin. While Desmond represented himself as an intermediary in the sale, Glackin's report said Desmond, businessman
JP McManus and
John Magnier were beneficiaries of the sale. Desmond strenuously disputed Glackin's findings. According to the Glackin Report, Hoddle Investments (the vehicle through which the deal was handled) executed two contracts with Telecom Éireann for the sale of the Johnston Mooney & O'Brien site for an aggregate price of £9.4 million, on 7 May 1990. The proceeds of the sale were lodged to an NCB account. According to the Moriarty Tribunal report, the next day, on 8 May 1990, £206,613.57 was withdrawn from one NCB account, converted into sterling £200,000 and transferred to the Aurum Nominees No.6 account at NCB (proxied to an offshore Ansbacher Cayman account) held for the benefit of then Taoiseach,
Charles Haughey. Aurum Nominees Limited was a company established by NCB for the benefit of its clients, and used at the time by several of the beneficiaries to the deal, including JP McManus,
Lochlann Quinn and Martin Naughton. Quinn and Naughton were owed money by Desmond and he used the proceeds of the sale to pay off his debt to them, according to the report.
Flood Tribunal Desmond gave evidence relating to the
Century Radio module of the
Flood Tribunal. He stated he had given former Fianna Fáil press secretary
PJ Mara a loan of £46,000 between 1986 and 1989, as Mara said he had run into financial difficulties. Desmond said he made the payments by cheque.
Moriarty Tribunal The
Moriarty Tribunal found that Desmond made substantial payments to
Taoiseach Charles Haughey. In September 1994, Desmond made a payment of £100,000 sterling to Haughey and in October 1996 he made a payment of £25,000 sterling. While Desmond claims these payments to be loans, repayable by Haughey, the Tribunal did not accept this explanation. Ultimately Haughey was forced to settle with the Revenue Commissioners, as it appears he had failed to declare the payments from Desmond. The Tribunal noted that the payments were made via the Swiss bank account of a company called Anesia Etablissement, Banque Scandinave en Suisse, Case Postale 901, 1211 Geneva 3, of which Desmond was the beneficial owner, via an account at Henry Ansbacher & Company to an account at Cayman International Bank Trust Company, held for Haughey's benefit. Desmond said Haughey asked him for the money in 1996 because of "a shortage of funds". Desmond also loaned money to Feltrim plc, which was at the time managed by Charles Haughey's son, Conor Haughey. In August 1991, Desmond loaned the company £55,000, made up of £40,000 loaned on 12 August 1991 and £15,000 on 28 August 1991. Conor Haughey told the Tribunal that the company was in danger of being liquidated and he approached Desmond for the money. The loan was never repaid, and was instead converted into equity.
Celtic Mist Desmond also paid £75,456 for the refurbishment of Haughey's yacht, the Celtic Mist, between 1990 and 1991, at a time according to the Tribunal, that Haughey earned between £69,764 and £72,354 a year as Taoiseach. Desmond said this payment was a loan, but the Tribunal disagreed, stating again that Haughey had settled with the
Revenue Commissioners in relation to the sum, having failed to pay Capital Gains Tax at the time. The Tribunal also found that the yacht itself amounted to an indirect benefit to Haughey. This was despite it being unable to find the source of the £167,073.90 paid for the yacht. The yacht was subsequently given to the Irish Whale and Dolphin Group by the family of Haughey and now operates as a maritime research vessel.
Esat Digifone Desmond was an investor in
Esat Digifone through his International Investment Underwriters (IIU) vehicle, ultimately owning 20% of the company. It was reported that he made up to £100 million in profit after selling his stake in Esat.
Football Desmond is the largest individual shareholder of the
Scottish Premiership football club
Celtic. Desmond previously held a stake in
Manchester United. He sold the stake to
Malcolm Glazer in 2005. In October 2019, Desmond purchased a 25% stake in
League of Ireland club
Shamrock Rovers.
Horse racing Desmond's racehorse
Commanche Court won the
Triumph Hurdle (1997), the
Irish Grand National (2000), the
Punchestown Gold Cup (2000), the
Lismullen Hurdle (1998), the
Christmas Hurdle (1998) and the
Spring Juvenile Hurdle (1997). ==Business holdings==