Longtime Montpelier director Justin Wiley joins TGSF board

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Longtime Montpelier director Justin Wiley joins

TGSF board

Brings experience, enthusiasm – and royal bloodlines –

to Foundation leadership

By Betsy Burke Parker

Justin Wiley is a natural for the job, say fellow steeplechase foundation trustees, with decades of business experience, years at the helm of one of the circuit’s most successful jump meets, a lifetime of equestrian knowledge and a Hall of Fame level horse pedigree that reaches back multiple generations.

The newest member of the Temple Gwathmey Steeplechase Foundation board of trustees, Wiley joined the group this winter. From his real estate office in Orange, Virginia, Wiley says he “looks forward to helping out.”

A lifelong rider and avid foxhunter, Wiley has owned steeplechase horses – alone and in partnership, for more than 30 years. His steeplechase knowledge runs deeper than sideline support: he spent almost two decades as co-director – with Brooke Royster, of Virginia’s Montpelier Steeplechase Foundation that runs the Montpelier Races in November at the former home of U.S. President James Madison.

He stepped away from Montpelier in 2020, and has been helping “on the horse side of things” at Charlottesville’s Foxfield meet since last year.

Joining the Gwathmey foundation was a natural, Wiley says. “(TGSF president Kathy Neilson) asked me. Yes was an easy answer.”

Trace Wiley’s trajectory

Wiley’s horse involvement predates his 1964 birth by many generations.

His father, Hugh Wiley, was an American and worldwide show jumping circuit darling, winning prizes in almost every title jumper classic in the U.S., England and Europe.

Wiley’s mother, Serena, was born and raised in south Yorkshire, England. She was a skilled rider and an avid foxhunter.

Her father, Roger Lumley, was the 11th Earl of Scarbrough, a British conservative party politician and a British army general. Serena – more formally, Lady Jane Lily Serena Lumley, met U.S. Equestrian Team show jumper Hugh Wiley when he was campaigning in England in the late 1950s.

They married in 1963 and had three sons. Justin is oldest.

Roger Lumley, 11th Earl of Scarbrough

Read more about Justin Wiley's grandfather HERE.

"Lawrence (1896–1969), 11th Earl of Scarbrough, was Grand Master of the United Grand Lodge of England, the governing body of Freemasonry in England and Wales, from 1951 to 1967. In this portrait he is wearing the robes of the Order of the Garter, the highest chivalric order in the United Kingdom."

After living in England a short time, Hugh and Serena Wiley moved back to Maryland in 1963. They lived and worked out of his great-grandfather's farm in Towson. Respected hunter-jumper show rider, trainer and breeder, Howard Firor was elected to the Maryland Horse Show Hall of Fame.

They moved to historic Oak Hill Farm in Palmyra, Virginia -- former Deep Run Hunt territory, in 1969.

Hugh Wiley rode on the 1956 and 1960 U.S. Olympic show jumping teams, but he stepped back from competition when he got married. He was a sought-after hunter judge, and the Wileys bred top show hunter-jumpers.

Hugh Wiley and Show Jumping Hall of Famer Nautical (r) and Master William on their way to Europe.

Photo: USET Foundation Inc.

Before Justin was born, Hugh and Serena Wiley spent a lot of time in Argentina, importing thoroughbreds to their Virginia farm for retraining to sell as show horses.

“Dad was always a strong proponent of thoroughbreds in the show ring,” Justin Wiley recalls his father’s ardor for what he called the perfect athletic package – movement, athleticism and brains.

Justin Wiley and his brothers, naturally, grew up riding under their parents’ careful supervision. “My father and mother taught us all to ride from an early age,” Wiley recalls. “But dad was pretty strict as an instructor. (Another horse show hall of famer,) Ellie Wood Keith Baxter was nicer about it,” Wiley says, when he got lessons with her.

Hugh and Serena conducted summer schooling sessions for upper level riders at Oak Hill.

Justin Wiley graduated from St. Annes Belfield school in Charlottesville, then studied history at Roanoke College.

After school, Wiley worked 1986 to 1991 for John Kluge’s Albemarle Farms. He served as assistant curator of the world-renowned carriage collection for of the late media mogul, one-time owner of the Harlem Globetrotters and once the richest man in America.

Initially, Wiley worked for the head gamekeeper at the estate, but Wiley soon switched to helping manage Kluge’s impressive carriage collection. His immediate boss was carriage museum director Owen Best. Best’s son, Greg Best, rode show jumper Gem Twist to dual Olympic silver medals.

The Carriage Museum at Morven Estate, Charlottesville

One of Wiley’s favorite parts of the job was escorting Kluge guests touring the collection – actors Gregory Peck, Nick Nolte and Jimmy Stewart were just a few of the estate’s big-name visitors.

They were in town for the Virginia Film Festival. Kluge’s one-time wife, Patricia, started the festival in 1988.

Wiley was also director of coaching for the Stratford Hall coaching weekend 1988 to 2004. Stratford Hall is Confederate Gen. Robert E. Lee’s ancestral home in Virginia’s Westmoreland County.

Wiley established the Blue Sky Drives charity coaching event that ran in Charlottesville 1995 to 1998.

The driving link had come through his father: Hugh Wiley was good friends with four-in-hand drivers, and steeplechase owners, the late Frolic Weymouth, Phyllis Wyeth and Marshall Jenney.

Justin Wiley is a member of the exclusive Coaching Club, a New York carriage group formed in 1875.

Moving into real estate sales was a natural progression after his museum career, Wiley says. He worked for Royer and McGavock and Hugh Wiley Realty Ltd. 1991 to 1999, then was an associate broker with Frank Hardy Sotheby’s 1999 to 2016.

Wiley family equestrian tradition

Born in 1927 in New Haven, Connecticut, Justin Wiley’s father, Hugh, was an Olympic show jumper, Pan American Games gold medalist and a member of the Maryland Horse Show Hall of Fame.

Wiley studied at the University of Maryland. He worked as an engineer and served in the U.S. Navy.

Hugh Wiley represented the U.S. in the 1956 Olympics held in Stockholm, Sweden. He was the top American finisher, 11th with Trail Guide ahead of Bill Steinkraus and Night Owl in 13th, and Frank Chapot on Belair, 27th.

The 1956 Olympic Show Jumping team: William Steinkraus on Night Owl, Hugh Wiley on Trail Guide, Warren Wofford on Hollandia (reserve pair for both the show jumping and eventing teams) and Frank Chapot on Belair.

©Chronicle of the Horse

Wiley won team and individual gold at the 1959 Pan Am Games in Chicago.

He rode at the Rome Olympics in 1960, seventh individually with Master William. George Morris was the highest-placed U.S. rider that year, fourth aboard Sinjon.

In 1955, Wiley was paired with a western-bred quarter horse cross, a palomino originally known as Injun Joe, renamed Nautical. Notoriously sensitive and tough to ride, Nautical flourished under the steady hand of Wiley. Together the pair wowed the show jumping world – they won a dozen Nations Cup titles and every top jumper class around the globe.

Hugh Wiley and Nautical in 1958

©Pony Light

In addition to sometimes theatrically rushing his fences, Nautical had a fun, trademark jumping style – he’d flip his flaxen tail in the air as he set down from a fence.

The bigger the jump, the bigger his tail would swish straight up as he landed.

Disney made a movie about it – The Horse With The Flying Tail (watch it HERE).

Nautical retired at age 17 in 1960, dying six years later at Wiley’s farm in Maryland.

Hugh Wiley died in 1999 at age 72 in Palmyra, Virginia.

Wiley and his brother, Peter, established Wiley Real Estate in Charlottesville in 2016. Wiley serves as the group’s principal broker in the firm that sells residential, farms and raw land. The Wileys also consults seller and buyers on conservation easements and other open space protection vehicles.

In 2000, Wiley wed Nancy Massie, daughter of sporting artist Sandra Massie Forbush and step-daughter of longtime Old Dominion Hounds master and steeplechase official Gus Forbush. (©Camden Littleton photo of Justin and Nancy, left)

Oldest daughter Lily was born in 2002 – she’s at Wofford College in Spartanburg, South Carolina. Son Hugh is studying at the University of the South. Daughter Georgina is a high school senior at St. Mary’s. She will attend Wofford College in the fall, rooming with steeplechase owner Mason Lampton’s daughter.

The Keswick Hunt link – Nancy was joint-master for eight years – gave Wiley a close association with Dr. Reynolds Cowles, which in turn led to his involvement with Foxfield.

Justin Wiley foxhunting with his children.

“I’m so happy to hear that Justin is going on the Gwathmey Foundation board,” says Foxfield board chair Cowles. “He’ll be a good addition.

“(Foxfield director Jack Sanford and I) have known Justin for a long time both through foxhunting at Keswick and working with him when he was clerk of course at Montpelier. This past year he joined our advisory board at Foxfield and has become an integral member of our race committee.

“Justin brings good experience in the running of a race meeting coupled with his knowledge of land and people in addition to being a horse owner.

“We’re very grateful for his help at Foxfield.”

The Foxfield Races team of Reynolds Cowles, Jack Sanford and Justin Wiley.

©Camden Littleton

Jumping at the chance

Wiley says his father only rode a few steeplechase races, and that he didn’t really want his sons to pursue race riding. But Justin Wiley has long been involved in racing as an owner.

In 1989, he had a 1/18th share of a horse called Eighteen Wheels. The syndicate was put together by Virginia Thoroughbred Association executive director Debbie Easter with trainer Woodberry Payne.

Wiley had a few wins with trainers Kathy Neilson and Ricky Hendriks in the ‘90s; his biggest was the New Jersey Hunt Cup in 1997 with Nuage D'Irlande, ridden by Michael Traurig and trained by Neilson.

From the 1997 "American Steeplechasing:"

The New Jersey Hunt Cup stretch produced a tight battle between Nuage D'Irlande (left) and S.S. Gold Crest. The former prevailed by a head for owner Hamilton Farm.

©Skip Dickstein

His Local Treasure won four hurdle races and more than $65,000, 2002 to 2006 for Hendriks.

“When Nancy and I got married, the focus changed to foxhunting and children.” Wiley moved away from racing but now, he’s back in the game. When Nancy stepped down from being master at Keswick, Wiley put together another partnership – Hard Game LLC.

“We started about four years ago. It includes Mike Massie, Rob Farmer, David Perdue and myself as managing partner. We currently have five horses, four of which are in training with Kathy,” Wiley says, including dual hurdle winner last fall, L’Avvacato.

L'Avvocato and the Hard Game connections in the winners circle at Camden in November.

Tod Marks photo

Wiley was brought onto the Gwathmey Foundation board of trustees by president Kathy Neilson. The board of trustees has met just once since he joined.

“Our current project is funding new safety vests for the active riders,” Wiley explains that the foundation is working closely with NSA on several safety initiatives targeted toward the jockey colony. “When Kathy asked me to get involved, I agreed readily because I love steeplechasing, I love the sport. I love the tradition.”

From the 2004 "American Steeplechasing:"

Justin Wiley's Local Treasure (right, Richard Boucher) benefitted from the disqualification of Too Irresistable (left) for missing a beacon, and captured Brookhill's feature, a $15,000 allowance hurdle for trainer Ricky Hendriks.

Trainer Kathy Neilson congratulates Gerard Galligan after winning a maiden claiming hurdle at Foxfield Fall Races in 2022, with Hard Game LLC's Hard Game.

©Douglas Lees

Temple Gwathmey Steeplechase Foundation Trustees - 2025

Justin Wiley

The Canvas Horse 2025

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