Skift Power Rankings: Michael O’Leary

Skift Take

Everyone wants to know O’Leary’s opinion – and he’s not afraid to give it.

Gordon Smith

For an airline renowned for charging customers for almost everything, Michael O’Leary is rather good at getting a freebie. “All you have to do is make noise,” he told Skift in a recent interview. 

Unlike many other names on this list, you won’t find a curated corporate page for Ryanair’s CEO on LinkedIn, Instagram, or TikTok. But that doesn’t stop the straight-talking Irishman describing himself as “one of the original creators of social media.”

O’Leary’s colorful – and sometimes controversial antics – can distract from the fact that he is an incredibly shrewd operator. He joined Ryanair as CFO in 1988 at a time when the airline was struggling on multiple fronts. 

O’Leary was famously inspired by the low-cost airline revolution taking place in the United States. In the early 1990s, his foresight brought him to Texas to meet Southwest co-founder Herb Kelleher, where the pair enjoyed a boozy evening talking shop. Kelleher helped inspire the young businessman to transform Ryanair from a clunky regional airline into a low-cost powerhouse.

Today, the Ryanair Group is Europe’s largest airline by most metrics. It flies more than 3.5 million passengers in an average week with its ‘Low Fares Made Simple’ mantra. 

It’s also one of Boeing’s most loyal customers. As the U.S. planemaker endures a torrid 2024, O’Leary has gone further than any other airline executive in his commentary. Speaking to Skift in March, he said Boeing “loves talking corporate bullsh*t.” Whether causation or correlation, many of Boeing’s top team were ousted a week later.

O’Leary has a rare combination of attributes that make him one of the most powerful names in global travel. His media savvy, unpredictability, and ability to drop a killer quote mean his reputation travels far beyond Ryanair’s European flight network. Having agreed to stay in post until at least 2028, and with a reported $100 million performance-related bonus in the mix, O’Leary’s frolics aren’t heading to the departure lounge anytime soon.

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