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Go Big Blue!

STEVE FLAIRTY: Remembering Billy Reed's Colorful Kentucky Derby Stories


Editor's note: Steve Flairty's column first appeared in NKyTribune.com (Northern Kentucky Tribune).


As the 149th renewal of the Kentucky Derby approaches, I’m awed to think about the number of words authors have written about the iconic event. The quantity of Derby books published is legion, and I’ve read my share. I might be “down the stretching it,” but all of them stacked up might go fourteen hands high — the approximate height of a small horse. That said, I believe there are a lot of good ones, as well as ones not worth the time, but my favorite is by the long-time and acclaimed Kentucky sportswriter Billy Reed, who, sadly, died in February 2022. His collection of previously published equine articles, released in 2003, called My Favorite Derby Stories (Butler Books), is fascinating reading because it is about people. Despite the glamour around many, that are just like us. And, of course, it’s about the horses… whom Billy deftly personifies through his words and presents interesting reading. Here are some examples.

Col. Matt Winn, who become known as “Mr. Kentucky Derby,” was a grocer’s son who took a longshot to buy a badly tottering Churchill Downs in 1902, organizing a group of investors to raise $40,000. He gave up his tailoring business to do so and he was all in. His rescue venture turned a profit in 1903 and Winn was soon “off to the races” as a promoter of the Kentucky Derby, making it one of the signature sporting events of the year. Reed noted that “from the 1920s until his death in 1949, Winn lived in a six-room apartment at the track, where he always entertained the Derby winners and many of his friends.” One writer said that Winn “lived the Derby 24 hours a day.”

Winn had answers for every time the Derby met great obstacles, such as when he revived parimutuel wagering in 1908 to replace cheating bookmakers, or when he judiciously handled the challenges of World War I and II with astute promotions to keep the Derby in the limelight. He had, said Reed, “the vision necessary to build the Derby, which was little more than a provincial race when Winn became the embodiment of Churchill’s spirit.”

The 1933 Derby had, literally a “fighting finish.” Officially, Broker’s Tip, ridden by jockey Don Meade, defeated counterpart Herb Fisher, riding Head Play, by a nose. Until this day, however, it’s debatable whether the outcome was judged correctly. The chief steward overruled three other stewards in judging the winner. And not only that, the two jockeys literally fought with each other while making the stretch run.

The grabbing of silks and hitting with a whip likely started when Fisher moved his horse to the left, close to Brokers Tip, to intimidate Meade. The two jockeys began to grab each other’s apparel during the exciting stretch run. Reed also reported that the two began mixing it up soon after the race in the jocks’ room until it was broken up by a Courier-Journal reporter.

The jockeys were brought back together to Louisville in 1983 by the Derby Festival Committee celebrating the race’s 50th anniversary. Each told their own side of the story, and they disagreed about who won the race, but had become friends by then. Writing about the 1933 race at Churchill Downs years later in 1983, Reed called it “the most famous Derby of all.”

Silky Sullivan, bought in 1956 at Del Mar for $10,700, was a good racer, but perhaps not a great one. There WAS something great about him, however, as Billy Reed wrote on the Churchill Downs website in 2000, saying that the horse “mesmerized the public.” Maybe it was because he had no sense of “quit” in him. As a two-year-old, he came from 27 lengths back to win the Golden Gate Futurity. Next year, he came from 40 lengths behind to only lose by a neck at the California Breeders’ Champion Stakes. Then, on his next try, he came from the rear to win a six-and-a-half-furlong allowance race.

Horse racing fans across the country loved Silky Sullivan for his amazing pluck, and even though he only finished only third in a tune up race at Golden Gate Fields, he became one of the three favorites to win the 1958 Derby. In Louisville, drug stores sold Silky Sundaes; bars sold drinks named after the horse. In the week before the Derby, Time and Sports Illustrated put Silky Sullivan on their covers.

Reed reported that a record number of $2 tickets for the May 3, 1958, Derby, and many of the horse’s supporters “planned on keeping them as souvenirs instead of cashing them.” With the great interest in Silky Sullivan and his knack for coming from way behind, CBS television used a split screen so that viewers could be watching Silky make his exciting move. Alas, Silky couldn’t deliver, and he finished the Run for the Roses third from last place, as Tim Tam was the victor. Interestingly, wrote Reed, the CBS race caller “mentioned Silky’s name five times and Tim Tam’s only once during the first mile and an eighth.” Sometimes style gets more looks than substance, it seems.

Not surprisingly, one of Reed’s stories paid tribute to one of, if not THE greatest racers of all time, Secretariat, who won the Triple Crown in 1973 in record-setting fashion. “Big Red” was humanely destroyed at Paris’s Claiborne Farm in 1989 because of a hoof disease that wouldn’t heal. In the aftermath, Reed said that the “flame has been extinguished, but the memory will glow so long as there are people who will always wonder if they’ll ever again see another quite as good as Secretariat, the big red horse who stole the country’s heart.”


Other horse profiles in Reed’s selections include Seattle Slew, Canonero II, Northern Dancer, and Alydar. He also adds stories of racing dignitaries such as owner William T. Young, trainer D. Wayne Lucas, and couples John and Donna Ward and Bob and Beverly Lewis.


These slices of horseracing done Kentucky-style are treasures that add to Reed’s own illuminating legacy.


Steve Flairty is a teacher, public speaker and an author of seven books: a biography of Kentucky Afield host Tim Farmer and six in the Kentucky’s Everyday Heroes series, including a kids’ version. Steve’s “Kentucky’s Everyday Heroes #5,” was released in 2019. Steve is a senior correspondent for Kentucky Monthly, a weekly NKyTribune columnist and a former member of the Kentucky Humanities Council Speakers Bureau. Contact him at sflairty2001@yahoo.com or visit his Facebook page, “Kentucky in Common: Word Sketches in Tribute.”

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