Leo P. McCullagh, Jr., passed away peacefully on April 8, 2026, at the Mayo Clinic in Jacksonville, Florida in the company of his wife, Penny, and niece Tracey. A Celebration of Leo’s life will be held on Friday, May 22, from 1 to 3 p.m. at the Aqua Grill restaurant in Ponte Vedra Beach, Florida.
Leo was born on December 2, 1949, in Montreal, Canada, to Leo P. McCullagh Sr., and Anna McCurdle McCullagh. He was the third of four boys; his brothers Larry, Tony and Michael all preceded him in death. Growing up in Montreal Leo excelled in school academically and as an athlete. He broke his neck playing football for Marymount High School, something that wasn’t discovered until years later when he joined the workforce, but he nevertheless continued playing competitive hockey after high school. He was also a world-class swimmer and was invited to try out for the Canadian Olympic team in 1968.
Leo attended Sir George Williams University, a public English-speaking institution in Montreal that merged with Loyola College to become Concordia University in 1974, the year before Leo graduated with a Bachelor of Commerce degree. In August of 1970, at a Nurse’s Night Out event at a local pub, Leo met a young nurse named Penelope Fewster; they were married on August 26, 1972, and to support them Leo finished his studies at night school while working during the day for Cockfield, Brown & Co., a local advertising company.
In 1978 he was named Canadian Director of Marketing for Benson and Hedges, a post he held for four years before joining Phillip Morris in 1982 as Vice President of Marketing for Asia. He and Penny lived in Tokyo and Hong Kong, traveled extensively throughout Asia, and along the way he became an accomplished at squash, which he played often when visiting Pakistan.
Leo and Penny moved to New York in 1987 when he was named Vice President of Sports Marketing for Phillip Morris USA. In that capacity he oversaw the company’s major sports marketing initiatives, including Marlboro Racing and Virginia Slims tennis, and established relationships in the sports world that he maintained throughout his life. In 1992 Leo joined the PGA TOUR in Ponte Vedra Beach, FL, as Vice President of Retail Marketing, a position he held until his retirement from the TOUR in 2007 when he started his consulting firm, McCullagh and Associates.
Robust both physically and in personality, it’s fortunate that Leo’s worldwide travels and business relationships gave him so many compelling stories to tell, because he was an extraordinary raconteur. He had great passion for sport as reflected in his business choices, and when his move to Florida coincided with the NFL’s expansion to Jacksonville, he and Penny became 20-year season ticket holders to the Jaguars. And once in Florida he became an avid golfer, although even a moderate degree of proficiency proved elusive. He was always, however, an outstanding dancer.
Leo is survived by his wife Penny; his niece, Tracey McCullagh and great niece Caitlin; his nephew Kerry McCullagh and great nephews Griffin, Callahan and great niece Delaney; and an enormous network of friends around the world. In lieu of flowers the family asks that donations be made to one of the following: Those Left Behind Cat Rescue, 3948 3rd Street #85, Jacksonville Beach, FL 32250; Towers to Tunnels Foundation, T2T.org; or Vicar’s Landing Members Fund (scholarship fund), 1000 Vicars Landing Way, Ponte Vedra Beach, FL, 32082.
