The Winding Road of Raymond G. Woolfe

Author’s Note: This article would not have been possible without the insight and assistance provided by Tudy Bunn (née Woolfe), I am indebted to her generosity to help tell the story of her father Ray Woolfe and the Colonial Cup.

On November 23, thousands of people will descend upon Springdale Race Course for the 50^th Running of the Marion duPont Scott Colonial Cup, presented by Mullikin Law. The races were created in 1970 as a means of boosting American steeplechasing during a time when its future seemed uncertain, and they proved an immediate success with the horse community. The Colonial Cup helped lift steeplechasing out of the dark days of the early ‘70s by proving that the sport did not need to rely on the big tracks of the north, who had so recently banished steeplechasing, to sustain it.

Today the Colonial Cup is most associated with Mrs. Marion duPont Scott, for whom the headline race is named. If anything, this honor undersells her contributions. She was the last private owner of Springdale Race Course, purchasing it from the estate of Mrs. Florence Clark and saving it from an uncertain fate. Mrs. Scott was the one who covered the international invitees’ travel expenses so that they could attend the Colonial Cup. It was Mrs. Scott who covered the Colonial Cup’s financial shortfall every year until her death. After her death, she bequeathed Springdale Race Course to the state of South Carolina exclusively for equine use in perpetuity, preserving the historic track for future generations.

However, Mrs. Scott did not do it alone. She relied heavily on her right hand man, who was just as instrumental to the success of the Colonial Cup, but has not gotten the same recognition: Raymond G. Woolfe.

It was Woolfe, with his knowledge gained from his time as an amateur jockey and a trainer, who was tapped to run Springdale Race Course after the death of founder Harry Kirkover. It was Woolfe who presented the idea to Mrs. Scott about having a fall race. It was Woolfe who got the state to sponsor the races. It was Woolfe who designed the fences that would be used, and laid out the track for the races. Mrs. Scott paid for it, but Ray Woolfe built it.

Raymond George Woolfe was born in Westfield, New Jersey on November 10, 1909. His father, George Woolfe, was a steamfitter in New York City, but he was killed when Ray was just two years old, leaving his mother Theresa to raise Ray and his older brother Webb alone. With support from her brothers, and Ray who modeled sailor suits for the Altmann’s Department Store, his mother managed.

Small for his age, the young Ray Woolfe struggled to make friends and was a frequent target of teasing and bullying. Concerned for her young son, Theresa asked a family friend to take Ray on an outing to his workplace: a nearby encampment of the 102^nd Cavalry Regiment. The decision was one that would go on to shape Ray’s life.

The bond was immediate and deep between Woolfe and the Essex Troop. He became a daily fixture among their ranks both after school and on weekends. As great as the troopers were to the boy, it was the horses that really drew him in. He did anything and everything he could, from mucking stalls to shining boots, to stay close to the horses. The troopers were so taken with the boy that they soon made him their regimental mascot, providing him with his own uniform and assigned him his own horse: a pony named Cricket.

This arrangement continued until Woolfe turned eighteen. Then, one of the regiment’s officers reached out to a horseman in Aiken, SC and asked him if he might have a place for a promising young rider. Soon after, Woolfe received a letter inviting him to stay in Aiken under the tutelage of Thomas Hitchcock, Sr. Hitchcock taught Woolfe everything he knew about steeplechase, building off of what the troopers of the 102^nd had already taught him about horsemanship. He taught Woolfe how to examine a Thoroughbred, how to judge its conformation and soundness, and how to condition it to run over fences. His son

Raymond (Raymie) Woolfe, Jr., later said “Dad quoted Hitchcock to me like most fathers quote the Bible.” It opened Woolfe’s eyes to new opportunities beyond just riding races, and he saw a real future for himself as a trainer of steeplechase horses.

However, wise old Thomas Hitchcock pointed out a problem in Woolfe’s plan. If he wanted to be a trainer, he had to ride as an amateur. During the Great Depression, the steeplechasing world was still very much divided by class. The social elite who rode as amateurs, for sport rather than for pay, looked down their noses at the professionals who rode for money, considered little better than mercenaries. If Woolfe rode as a professional, he would make money, but the stigma meant he might not be able to achieve his true goal to work as a trainer. If he rode as a gentleman jockey, he might not be paid, but he would stand a chance of becoming a trainer down the road.

Woolfe made his decision, and joined the ranks of the fabled gentleman jockeys to chase his dream. (Although Raymie recalled that his father once told him “Gentleman jockeys took money under the table, professional jockeys took money over the table, and amateur jockeys were too dumb to take any at all.”)

So, Mr. Raymond G. Woolfe began to appear on the race cards printed in programs at the hunt meets around America. In time he established himself as one of the top riders on the circuit, winning the amateur jockey championship in 1938 and 1939. By the early 1940s Ray Woolfe shifted from riding to his true dream, training steeplechasers. His big break came in 1943 when he became the trainer for Mrs. Marion duPont Scott and her powerful Montpelier stable. In this capacity, he trained two of Mrs. Scott’s steeplechase champions, Shipboard in 1956 and Benguala in 1960, as well as numerous other stakes winners.

Since the early 1940s Woolfe moved his winter base to Camden, SC where he stabled and trained at the Springdale Training Center. He became close friends with Carolina Cup founder Harry Kirkover and soon helped him with running the track and organizing the races. When Kirkover died in 1958, the Carolina Cup Committee asked Woolfe to serve as the manager of the Carolina Cup as well as Springdale Race Course and Training Center. He accepted and would serve in this post until his death.

It was in this capacity that Ray Woolfe conceptualized the Colonial Cup during the summer of 1968. To help pay for the race, he planned on the sponsorship of private donors. Woolfe reached out to Lieutenant Governor John West to ask if donations to the race could be tax deductible if it was an official state sponsored event. When he got the affirmative on that idea, he went to Mrs. Scott who gave her blessing. With the backing of Mrs. Scott and Lt. Gov. West, the state of South Carolina agreed to sponsor the inaugural running of the Colonial Cup steeplechase in 1970 as an official event in South Carolina’s Tricentennial Celebration.

Woolfe lined up seventy-seven sponsors at $3,000.00 each, but the real kicker would come during a meeting of the state’s Tricentennial sports committee.

“One of the PGA officials asked the committee chairman if the Tricentennial would put up a purse in six figures for a golf tournament. When the chairman said no, the PGA man replied, ‘Well, if you don’t have a golf tournament for six figures, you’d better come up with some different kind of tournament.’ He sounded so much like a horseman that it made me think I’d have to come up with a six-figure purse for the Colonial Cup. There was already a $50,000 steeplechase, the Temple Gwathmey, and it wouldn’t be different to have another race worth $50,000.”

Thus, he decided the Colonial Cup should have a $100,000 purse, making it the first $100,000 steeplechase race in North America and the second richest in the world behind only the Grand Steeple-Chase de Paris. Their hard work paid off on November 14, 1970 when twenty-two horses, thirteen American and nine foreign, went to the post in the inaugural running of the Colonial Cup. The race was won by Top Bid and proved Woolfe’s beliefs that it was these country hunt meetings, not the major tracks, that formed the backbone of American steeplechasing.

Ray Woolfe continued to run Springdale and nurture the Colonial Cup, the Carolina Cup, and the Training Center. On August 9, 1975, Ray Woolfe died of a heart attack at his home at just sixty-seven years old. His death left a deep void at Springdale Race Course. When the Carolina Cup Committee met to choose a successor, Mrs. Scott stood up, and in an uncharacteristically loud voice, declared “No one can ever replace Ray Woolfe.”  Nevertheless, his close friend Dale Thiel was chosen to succeed Ray as Director.

The Colonial Cup would run for forty-six years, crowning twenty-seven of its winners as Champions, before it was discontinued after 2016. It briefly returned on the same day as the Carolina Cup in 2018, then lay dormant until its return last year.

Hopefully, this time it’s here to stay.

The first time I met with Ray’s daughter, Tudy, we stood in what is now the Austin and Sally Brown Founders Room and discussed the Cup. She remembered the room as the old Cup office, built at her father’s request, and recalled her time working for the Cup and for her father. She told us about how she used to lick stamps in Mr. Kirkover’s ballroom, hand address envelopes in the basement of the Court Inn, and sit behind her desk in that small office looking out at Springdale. It was one of these times that Ray began to think aloud what a shame it was that the property hosted just one race a year. He thought about how Springdale helped open the steeplechase season in March with the Carolina Cup and wondered if one day it might close the season in November.

More than fifty years later, the Colonial Cup will close out the National Steeplechase Association’s 2025 racing season. The second race of the day will be the Raymond G. Woolfe Memorial.

“I don’t think a man ever loved steeplechasing like my Dad. Steeplechasing is a consummate passion, yet some of the people in it don’t seem to give a damn. My father was one of the people who gave a damn, so were Mrs. Scott and Harry Kirkover…” – Raymond (Raymie) G. Woolfe, Jr.