Irvin Stanley Naylor

Irv Naylor died peacefully on Tuesday 20 October 2026 at his home in Reisterstown, Maryland, aged 91. No cause of death was made public.

His death was announced by McDonogh School, whose head of school Dave Farace said that buildings bore his name, awards carried his spirit and the students whose paths he had quietly shaped would carry his legacy forward. The National Steeplechase Association called his passing an immeasurable loss to the racing community. He was survived by his wife Diane, his children and grandchildren. A celebration of his life was to be held at a later date.

Irvin Stanley Naylor was born on 26 June 1935 in Stevenson, Maryland, the son of a filling station operator in nearby Pikesville. His introduction to horses came through his grandfather and an uncle, both blacksmiths.

In 1942, aged six, he entered McDonogh School near Baltimore as a scholarship student, then a military school. Over twelve years there he was a leader and a strong athlete, competing on the varsity wrestling and riding teams for all four years of Upper School and captaining the Troop, the school's cavalry squad, in his senior year. He graduated with the Class of 1954 and went on to Miami University in Ohio. He later said that much of his financial and social success went back to McDonogh, where he learned how to study, how to prioritise, manners and values.

Naylor began in packaging. In 1960 he launched Lok-Box, a company producing wooden boxes, and in 1968 he added Cor-Box, which made corrugated boxes.

His real passion, though, was skiing. In 1964 he opened Ski Roundtop in York County, Pennsylvania, the first resort of what became Snow Time, Inc. The company went on to take over the ski area near Fairfield, Pennsylvania that was renamed Ski Liberty, and to operate Ski Windham in New York. When Whitetail Resort opened near Mercersburg in 1990 as a well funded luxury rival, the competition was fierce, and in August 1999 Snow Time bought Whitetail. For decades Roundtop, Liberty and Whitetail were among the main day ski areas for skiers from Baltimore and Washington. In September 2018, as Naylor moved into retirement, Snow Time and its three Pennsylvania resorts were sold to Peak Resorts in a deal reported at 76 million dollars. "I am extremely pleased to pass along the stewardship of Snow Time and our three mountain resorts to Peak Resorts," he said at the time.

In racing he was first a rider and then an owner. He took up fox hunting at 15, became joint master of Pennsylvania's Rose Tree Hunt, rode in point-to-points and from 1967 rode 41 races on the National Steeplechase Association circuit as an amateur timber jockey, including four Maryland Hunt Cups in which he finished fourth twice, fifth and seventh.

After the 1999 fall that left him paralysed, he built one of the strongest jumping stables in the United States. Racing in green, white and gold silks, his horses won seven NSA leading owner titles from 2010, the last in 2023, and in 2024 the Naylor Stable passed George Strawbridge's record to become the NSA's leading all time owner. His runners included the Eclipse Award winners Black Jack Blues (2011), Dawalan (2015) and Rawnaq (2016), division leaders Gold Charm and Bercasa, and Grade 1 winners such as Belfast Banter, Too Friendly and Tax Ruling, with 26 graded stakes wins in all. He won the Maryland Hunt Cup three times as an owner, with Make Me A Champ in 2005, Askim in 2008 and Withoutmoreado in 2023, and received the Hunt Cup's S. Bryce Wing Award in 2000 for his contribution to Maryland timber racing.

Naylor met Diane Gregory at a trade show in Chicago in 1970, and they were married for 52 years. Diane Naylor became an equally familiar figure on the steeplechase circuit. They had three children, Scott, Peter and Vivian, and grandchildren including Scott C. Naylor II, Sarah Naylor McPhee and Leah Naylor-Ickes. The family lived in Reisterstown, Maryland, and earlier in York, Pennsylvania.

On 17 April 1999, aged 63 and with the Maryland Hunt Cup in his sights, he was thrown in the Grand National timber stakes at Butler, Maryland. His horse fell on him and broke the C5 vertebra in his neck, leaving him paralysed from the neck down; he later regained the use of his arms. The injury ended his skiing and riding, and he became an outspoken advocate for stem cell research. In 2023, unable to travel to the steeplechase awards dinner in Aiken, South Carolina, he wrote that it was ironic he could not be there because of a horse, having been invited because of his horses.

Naylor's mark is visible in three worlds. The ski areas he founded or acquired, Roundtop, Liberty and Whitetail, remain among the busiest in the Mid-Atlantic. In American jump racing his stable holds the record as the National Steeplechase Association's leading all time owner, a status built largely after the injury that ended his own riding.

At McDonogh School his name is on the Naylor STEM Building, the Naylor Wrestling Room, the Naylor Reference Room and the Naylor Scholarship Fund, and he also funded the Eagles Nest indoor riding ring and the Irvin S. Naylor Family Endowed Headmaster's Fund in honour of former headmaster Bo Dixon. He served twelve years as a trustee, was later trustee emeritus, entered the school's Athletic Hall of Fame in 1995 and received its Distinguished Service Award in 1997. In 2004, on their 50th reunion, his classmates created the Irvin S. Naylor Courage Award for members of the McDonogh community who show outstanding courage in overcoming adversity.