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In February 2020 O'Leary suggested that airport security should focus on single Muslim men, and called obese passengers "monsters".

According to the Bilderberg Group, O'Leary was to attend the Bilderberg Group in 2015. O'Leary was also seen attending the 2017 Bilderberg meeting in Washington D.C.

In February 2015 he revealed in an interview in The Sun that he was offered the starring role in The Apprentice reality game show, but turned it down for family reasons before it was eventually offered to and accepted by Lord Sugar.

In May 2014 O'Leary was highly critical of a 24-hour strike by Aer Lingus cabin crew, staged on 30 May 2014. Aer Lingus, whose biggest shareholder at the time was O'Leary's company Ryanair, had to cancel 200 flights and disrupt travel plans for 200,000 people. O'Leary accused Aer Lingus of "mismanagement" of its employee relations, called for the sacking of a board member, and said the striking employees should be punished by having their discount travel incentives withdrawn for a year.

However, more than a decade later, in 2013 he said, while at the Paris Air Show, that he wanted to sell cheap flights from the U.S. to Europe for as low as 10 euros ($13) or $10, if conditions were right. He said that he needed a fleet of at least 30 twin-aisle aircraft and access to ports (e.g. major U.S. and European cities, in the airline industry there are so called slots or sometimes gates, often regulated by law, and without obtaining them it is impossible to have regular service to airports). Despite his claims in 2002, there were so called budget airliners in the past – for example Laker Airways flights from London to New York in the late 1970s or long-hauls at budget-fares on other continents like AirAsiaX in Malaysia and the Australian Jetstar Group.

Reacting to the decision to close European airspace in April 2010 over worries about the ash plume from an erupting Icelandic volcano, Eyjafjallajökull, he said "there was no ash cloud. It was mythical. It's become evident the airspace closure was completely unnecessary." One study concluded that serious structural damage to aircraft could have occurred if passenger planes had continued to fly.

In 2007, he was forced to retract a claim that Ryanair had cut emissions of carbon dioxide by half over the previous five years; the claim should have been that emissions 'per passenger' had been cut by half. O'Leary has been reported to have impersonated a journalist in an attempt to find information passed on to a newspaper following a safety incident on a Ryanair flight. On occasion he has apologised for personal attacks under threat of legal action. He has been criticized by a judge for lying, who said he was lucky not to be found guilty of contempt of court. In April 2017, he called concerns about climate change "complete nonsense".

He breeds Aberdeen Angus cattle and horses at his Gigginstown House Stud in County Westmeath. In 2006, his horses War of Attrition and in 2016 Don Cossack have won the Cheltenham Gold Cup and the 2016 Grand National with Rule The World. He also won in both the 2018 Grand National and 2019 Grand National with Tiger Roll.

In 2004 he purchased a taxi plate for his Mercedes-Benz S-Class, to enable it to be classified as a taxi so that he could legally make use of Dublin's bus lanes to speed up his car journeys around the city. A press report suggested that since he had stopped driving his own taxi, he has employed a driver with full PSV licence. In 2005 the Irish transport minister expressed concern at this abuse by O'Leary and others.

O'Leary lives in Gigginstown House near Delvin in County Westmeath. He married Anita Farrell in September 2003, and they have four children.

O'Leary has also been a Manchester City supporter since an early age. In 2003, he was offered the opportunity to buy a stake in the club but believed the potential benefits did not outweigh the risk and preferred to visit England to watch a few matches each season. He wore a Manchester City shirt when unveiling Ryanair's new destinations to and from Manchester Airport in 2011.

In 2002 he said that his company is against any long-haul transatlantic services, stating that:

Under O'Leary's management, Ryanair further developed the low-cost model originated by Southwest Airlines. O'Leary described the ancillary revenue model in a 2001 interview, saying "The other airlines are asking how they can put up fares. We are asking how we could get rid of them." The business model envisioned by O'Leary uses receipts from on board shopping, internet gaming, car hire and hotel bookings to supplement the ticket revenue from selling airline seats. Savings are also made by negotiating discounts with airports for reduced landing fees. In many cases, regional airports have made no charges so as to secure flights that bring passengers and wealth into their area. The deregulation of Ireland's major airports and a transformation of traditional full-service airlines are among his demands.

O'Leary has a reputation for loose talk in the airline industry and among its regulators. Many press articles have described him as arrogant, and prone to making comments which he later contradicts. He has been extravagantly outspoken in his public statements, sometimes resorting to personal attacks and foul language. His abrasive management style, ruthless pursuit of cost-cutting and his explicitly hostile attitude towards corporate competitors, airport authorities, governments, unions and customers has become a hallmark. He was reported to have been aggressive and hostile in dealings with a woman who was awarded free flights for life in 1988.

While at Stokes Kennedy Crowley, O'Leary had met Tony Ryan, head of Guinness Peat Aviation, a leasing company (GPA). Ryan was one of KPMG's clients and O'Leary advised Ryan on his personal income tax affairs. In 1987, Ryan hired O'Leary as his personal financial and tax advisor, where Ryan's main interest was in GPA.

O'Leary grew up near Mullingar, County Westmeath. His father was the part owner of a textile factory. He was educated at Clongowes Wood College, County Kildare before studying business and economics at Trinity College, Dublin. After graduating in 1983, he worked as a trainee with Stokes Kennedy Crowley (later known as KPMG), studying the Irish tax system. He left after two years in 1985, setting up profitable newsagents in Walkinstown and Terenure, Dublin.

Michael Kevin O'Leary (born 20 March 1961) is the Chief Executive Officer of Ryanair. He is one of Ireland's wealthiest businessmen.