In 2003, frustrated at being caught in traffic in his native Westmeath, the businessman registered his Mercedes as a taxi, allowing him to avoid the gridlock and zip through the restricted access bus lanes instead.
His latest predicament, however, may yet prove his most difficult to fix. Ryanair, faces a compensation bill of up to €20m for the flight cancellations “mess”.
Reputation-wise, both he and the firm have suffered a significant blow across the bows.
The cancellation fiasco, affecting around 2% of flights, was described by the chief executive as a self-inflicted “mess-up” caused by a backlog of pilots taking overdue annual leave.
Typical of the outspoken boss’s desire to spin his way out of a corner, O’Leary insisted the firm was “not short of pilots”.
He is no stranger to controversy, his open and frank press conferences often peppered with off-the-cuff remarks.
Plans to charge for using the toilet mid-flight, allowing mobile phones on board, and — announced this month— ending its policy of allowing non-priority passengers to have two items of hand luggage have courted attention.
He has previously compared himself to “the messiah” and said people see him as “Jesus, Superman, or an odious little shit”. He has admitted to being a “Neanderthal” and a climate change denier.
His latest PR disaster, however, may have much greater side effects than price hike plans or baggage restrictions. “Clearly there’s a large reputational impact for which, again, I apologise. We will try to do better in future,” he said.
Despite the PR storm surrounding the flight cancellations, O’Leary has refused to bow to renewed calls for him to quit.
He previously told the Westmeath Examiner in 2009 that he expected to stand down by the time he was “50/51”. Five years past that expiry date, O’Leary remains in the thick of the action more than ever before.