Stewart Kenny, one of the most influential figures in Irish business, is widely recognized as the driving force behind Paddy Power, the renowned bookmaker that grew from a domestic chain into a €10 billion international betting powerhouse. After nearly three decades of dedicated service, Kenny has stepped down from his role as a non-executive director at Paddy Power Betfair, marking the end of a remarkable chapter in the company’s history.
Humble Beginnings and Early Career
Kenny’s journey in the world of bookmaking began in London, where he worked as a Ladbrokes shop manager. This formative period gave him crucial insights into the betting industry and laid the groundwork for his future ventures. Upon returning to Ireland, Kenny worked for various local bookmakers before setting up his own shop under his name, demonstrating both entrepreneurial flair and a deep understanding of the Irish gambling market.
The Formation of Paddy Power
In 1986, Kenny partnered with Terry O’Reilly to create Kenny O’Reilly, a bookmaker business that was later sold to UK betting giant Corals for IR£3 million. However, the ambition of the partnership didn’t end there. Just days after the deal was finalized, Kenny and his partners launched a new bookmaker chain, determined to stay active in the market.
The pivotal moment arrived in 1988 when Kenny’s business merged with two other major Irish players, the Richard Power Group and Corcoran’s. The merger birthed Paddy Power, a bold move aimed at building a bookmaker with the size and resilience to challenge British bookmakers, who had already secured over 20 percent of the Irish betting market at the time.
Kenny assumed the role of chief executive, embarking on a mission to turn Paddy Power into a market leader. Under his leadership, the company grew from a small player with an 8 percent market share to a dominant force, quadrupling its presence in Ireland before expanding globally.
Leading Paddy Power to Public Listing and Beyond
During Kenny’s tenure as CEO, Paddy Power made several strategic moves that would lay the foundation for its international success. In 2001, Kenny oversaw the company’s listing on the Irish Stock Exchange, a significant milestone that transitioned Paddy Power from a domestic bookmaker to a dynamic, publicly traded betting group.
Kenny stepped down as chief executive in 2002 but remained actively involved in the company. He briefly served as chairman from 2002 to 2003 and has since contributed as a non-executive director on the board. His strategic insights and deep knowledge of the industry have been integral to key decisions, including the monumental 2016 merger of Paddy Power with Betfair, which created one of the world’s largest online gambling groups—Paddy Power Betfair.
The End of an Era
In 2025, after a remarkable 28-year tenure with the company, Stewart Kenny officially stepped down from Paddy Power Betfair’s board. In paying tribute, Chairman Gary McGann emphasized Kenny’s role in transforming a modest, domestic bookmaker into a global leader.
“He was instrumental in creating a highly successful international business from a small domestically focused retail operation at inception,” McGann noted, highlighting Kenny’s pivotal influence in the company’s evolution and the seamless merger with Betfair.
Stewart Kenny’s Net Worth and Personal Life
While precise figures for Stewart Kenny’s net worth remain private, industry estimates place his fortune in the range of €30-50 million, considering his substantial stake in Paddy Power during its early growth stages and his influential role in the company’s expansion and public listing. Kenny’s wealth stems from the sale of Kenny O’Reilly, the subsequent success of Paddy Power, and his enduring role within the business, including the lucrative merger with Betfair.
Despite his high-profile career, Kenny is known to maintain a relatively low public profile. Details about his personal life, including family, are kept largely out of the spotlight, aligning with his preference for a quiet, business-focused persona.
A Legacy of Innovation and Resilience
Stewart Kenny’s legacy is defined not just by the financial success of Paddy Power Betfair but also by his ability to reshape the Irish and global betting landscapes. From navigating fierce competition from British bookmakers to leading a public offering and orchestrating a major merger, Kenny’s career is a case study in business acumen and long-term vision.
His departure from the board closes a significant chapter in the company’s history, but the foundations he helped lay will continue to influence Paddy Power Betfair’s trajectory for years to come.
What’s Next?
Though stepping away from Paddy Power Betfair’s board, Kenny’s expertise and reputation in the gambling sector remain highly respected. Industry insiders speculate he may continue to advise or invest in other projects within the broader entertainment or sports betting sectors. Regardless of what lies ahead, Stewart Kenny’s contributions to the world of bookmaking have already left an indelible mark.
As the industry continues to evolve, Paddy Power Betfair’s ongoing success stands as a testament to Kenny’s vision and the enduring impact of his leadership over the past four decades.