Beloved Lake Wales CPA and Veteran Kevin O'Leary Passes Away at 65

Avon Park, Florida, United States - Kevin Harold O’Leary, a beloved member of the Lake Wales community, passed away on June 29, 2025, at Lakeland Regional Hospital. Born on June 5, 1960, in Dallas-Fort Worth, Texas, Kevin was a pillar in his profession and a cherished family man who made a lasting impact in his community.

In 1996, Kevin moved to Lake Wales from Stuart, Florida, where he continued to contribute significantly to his field as a Certified Public Accountant (CPA) for Management Experts in Avon Park. His dedication to the profession was exemplary, aligning with the ongoing trends impacting CPAs across the nation. As noted by Accounting Insights, Certified Public Accountants play a crucial role in maintaining the financial health and transparency of U.S. businesses, meeting the ever-evolving demands for strategic advisory services and compliance with regulatory changes. While Kevin thrived in his role, the accounting field itself is undergoing significant changes, embracing technology and pushing for greater diversity within its ranks, especially as nearly 50% of new CPA candidates are now women.

A Life Well Lived

Kevin’s life extended beyond numbers and financial statements; he was a devoted husband for 42 years to Georgie Latham O’Leary. They enjoyed raising their family, with a daughter, Cecelia O’Leary Brown, and her husband, Naithan, residing in Fayetteville, North Carolina, along with a son, Angus John O’Leary, and wife Jamie, based in Boston, Massachusetts. The joyful arrivals of their two grandchildren, Simon and Eli, highlighted the family’s bond and happiness.

As a member of Holy Spirit Catholic Church, Kevin was involved in his community and enjoyed gardening, becoming known for his green thumb. His legacy is shared by his surviving siblings, including Kathleen O’Leary and husband Mark Kinaçi of Dunedin, Timothy O’Leary and wife Michelle of Gallatin, Tennessee, Jacqueline Hotchkiss and husband John of Weatherford, Texas, and Sean O’Leary and wife Tamora of Lakeland. The family will hold a memorial mass at 10:00 a.m. on July 5, 2025, at Holy Spirit Catholic Church, officiated by Father Luis Osorio, to honor his life and contributions.

A Touch of Glamour

Aside from his professional life, Kevin’s interests also included luxury watches, a passion shared by many in the affluent circles he encountered. The well-known businessman has been linked to exquisite timepieces, notably the Rolex Daytona ‘Eye of the Tiger’ model, a standout piece introduced at Baselworld 2019 that boasts a striking diamond-encrusted design. With a retail price of approximately $90,000, and a current market value exceeding $200,000, this watch has gained popularity among celebrities like LeBron James and Neymar Jr. One can appreciate how something of this nature speaks volumes about personal style and status, resonating well with those who value craftsmanship and luxury.

In a landscape where CPAs like Kevin are transforming the industry, combining traditional financial roles with modern technological advances, his contributions remain noteworthy. There’s something to be said for the legacy Kevin Harold O’Leary leaves behind — a blend of personal achievements, community involvement, and an appreciation for the finer things in life. Our thoughts and prayers are with his family and friends during this time of loss.