He Alone Made it What it is Today
By Teresa Genaro, Hello Race Fans Contributing Editor

So began a 1949 New York Times article by Arthur Daley on the passing of Matt Winn. The article was called “The Passing of a Legend,” and what he “made” is the Kentucky Derby.

Matt Winn, a racing impresario if ever there was one, worked at a dozen or more tracks in his life, but this Louisville native’s heart was always at Churchill Downs. As a boy of 14 in 1875, he saw the first Kentucky Derby, and he saw every one after that until his death in 1949. He hung on to catch the race’s 75th birthday.

William H.P. Robertson, in The History of Thoroughbred Racing in America, called Winn “a Moses who led the sport through trying times”; his business acumen, rather than his passion for racing, led him to join a group that bought the failing Churchill Downs in 1902, and the revival of the race track and the rise of its signature race are often attributed solely to Mr. Winn.

His single-mindedness was legendary. Dissatisfied with Churchill’s racing dates, Winn took on the Western Turf Association in Kentucky; later, joining forces in New York with James Butler, he did the same thing on behalf of Empire City, this time battling the Jockey Club. He won both times.

When asked by the United States government to suspend the Kentucky Derby in 1943 because of World War II, Winn declined. That year, Count Fleet won the Roses and the Triple Crown.

A 1974 article in Sports Illustrated by Frank Deford quotes Brownie Leach, who served as Winn’s public relations director: ” ‘He was a showman and he sold the Derby, but he cared for it, too. His major concern for the Derby was making it bigger year by year and having nice people come to it.'”

Robertson indicates that it was in the early 1910’s that Winn transformed the Derby from what Daley called “a bush track horse race” into “the turf’s No. 1 event.”

According to Robertson, at that time the big races for 3-year-olds were the American Derby, the Realization, and the Belmont. Winn wanted his Derby to be more important, more valuable than any of them, and several events over the next few years helped Winn elevate the profile of the race. 1911 saw the introduction of the $2 win ticket, and that year, Donerail set a new track record in winning the Kentucky Derby; a win ticket on him got you the biggest payoff in history: $184.90 (Robertson).

Four years later, in 1915, the filly Regret, owned by Harry Payne Whitney, headed west from her New York base to try to become the first female to win the Kentucky Derby in its forty year history, and her presence and victory pushed the Kentucky Derby even further into America’s consciousness.

The triumph of Regret, a filly and a Whitney filly as well, was perfect. It fired imaginations everywhere.
– Arthur Daley

Winn viewed her victory through his dual prism of racing fan and shrewd businessman, according to Edward Hotaling in They’re Off: Horse Racing at Saratoga, in which he quotes Winn: the Derby “needed only a victory by Regret to create for us some coast-to-coast publicity, and Regret did not fail us—The Derby was thus ‘made’ as an American institution.”

This Kentucky-bred racing prophet preached the gospel of racing through the United States and into Mexico, and those of us back on the East Coast, where Winn worked as a steward at Empire City, like to think that it was our filly that helped put America’s premier horse race on the map. But as Arthur Daley points out, we can’t take too much credit: “The Kentucky Derby is a monument to him. It’s his baby and his alone.”

A version of this article previously appeared at Brooklyn Backstretch and on The Rail.

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  • Marshall Cassidy

    Matt Winn was certainly the dynamo American Racing could now benefit from philosophically as your writing suggests. But when I think what Churchill Downs has done with their Kentucky Derby over the years to further maximize the race’s popularity, and more importantly their corporation’s market value, I then wonder if the track’s current management might have corrupted Mr. Winn’s simpler vision.

    110 years ago race tracks were equally competitive among themselves if not more so, but then their aims might have been more narrowly focused on regional and personal identity Racing issues. Today’s relative conglomerate thinking of major businesses such as Magna Entertainment and its subsidiaries, and Churchill Downs’ several corporations, ultimately serve the profitability interests of their stock holders’ accounts. Such considerations as a track’s bragging rights over who put on the best race, or attracted the best horse seem a lot less important in today’s story of horse racing, Matt Winn’s extraordinary talent notwithstanding.

    No judgment intended here, really; just a small recognition that times are very different.

  • I agree, Marshall. I like to think, or hope, that today’s racing world, different as it is, is also more democratic and more open than the older days…as much as I like to read about them and wish that I’d been around to experience them. The sport has lost a lot, certainly, but perhaps it’s also gained, as control and participation have shifted from a privileged few?

  • Marshall Cassidy

    Well put, and I agree with you.

  • Marshall Cassidy

    Yes, Teresa, I agree with you as control and participation have shifted from a privileged few… I agree to the degree that those who have replaced the privileged few are capable of sustaining the sport/business of horse racing.

    That organized horse racing developed somewhere, in the Middle East perhaps, through the passions and financing of those who could afford their expensive pastime is not argued. That it spread to the English colonies and elsewhere through moneyed people is also accepted as history, no problem there either. Now that America’s wealthiest support a much smaller fraction of breeding and racing enterprises, such an economic conversion does not necessarily equally imbue any mantel of sustained passion to those who do lead our industry today, as you might also agree.

    What might have been considered sport at one Finish Line Clubhouse box seat and business at another up the stretch in the Grandstand a hundred years ago, has mostly reversed polarity and diminished some of the sport’s halo. I’m not convinced today’s openness and democracy translate well enough for healthy growth beyond the latest televised super race, or speedy OBS two furlongs workout. I’m probably wrong, but there seemed to be a reliable foundation then that would keep it all going, from foaling to burial, from barn to barn, from race track to race track, from decade to decade.

    Thoroughbred racing for Everyman is a noble goal!

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