He has graced the boards of big name public and private companies and has an enviable business contacts book.
Brought up in Donegal, he was educated at Campbell College, Belfast and Trinity College, Dublin. He qualified as a solicitor in 1973 and joined A&L Goodbody, making partner in just six years.
He led Goodbody's expansion, opening its New York office in 1979. He became managing partner in 1982, retiring 12 years later at just 45, but is still a consultant.
Osborne led the restructuring of Goodman International during Ireland's first ever examinership.
He joined Ryanair as a director in 1995 and steered the company through its flotation.
He backed Fresh Mortgages in 2006, along with Anglo's Sean FitzPatrick.
As far back as 2004 he saw that things in the property market were becoming untenable, when the yield on a deal on Galway's Shop St was more than one near London's Ritz Hotel.
Bookseller Eason recently appointed him chairman. He is a non-executive director of cement giant James Hardie Industries and chairs fund manager Pilot View Capital.
He's an investor in healthcare clinic group Centric Health, and Sentenial, an Irish company that provides debit card technology for banks.