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    By Bill Doolittle
    Photo by Adam Mescan

    How much do you know about Macbeth II?

    No, not a sequel to the Shakespeare play. The horse that won the Kentucky Derby in 1888.

    Not much? Me neither.

    Macbeth II is pretty much lost in the fog of time — as obscure as 1878’s Day Star, the winner of the fourth Kentucky Derby. Or the 1898 winner, Plaudit, piloted by African-American jockey Willie Simms, who went two-for-two in the Derby.

    Certainly there were memorable Derby moments in the 19th century — Aristides winning the first in 1875 — though not so much on years that ended in “8.” But when the Kentucky Derby rolled into the 20th century, big things began happening nearly every time the calendar year ended in “8” — 1908, 1918, 1928…and right on through the decades.
     

    1908
    Col. Winn saves the Derby

    Col. Matt J. Winn saved the Kentucky Derby from a powerful nationwide reform movement that wanted to abolish gambling and had set its sights on Churchill Downs and the Kentucky Derby. The reformers backed the Republicans, which had long been the “out” party in Louisville’s City Hall, and swept James Grinstead into the mayor’s office. Grinstead pledged to shut down gambling at Churchill Downs and got laws passed to close down the Kentucky Derby if betting was allowed on Downs ground.

    Winn had already saved Churchill Downs in 1902, when he took over the collapsing fortunes of the track and got it up and going again. He had also taken steps to make the place less of a gambler’s den and more of a family place, with a Kentucky Derby that was celebrated as a social affair. But Grinstead had police ready to bust the track.

    Winn got to work with a team of lawyers and found, as he thought there might be, an old state statute that specifically permitted pari-mutuel betting. It was something Col. Meriwether Lewis Clark had seen work in Paris and gotten legalized when he started the Kentucky Derby in 1875. Pari-mutuel betting is bettor vs. bettor (as opposed to bettor vs. house like at a casino), with the track running the operation for a percentage of the action. Another percentage goes to the horsemen in purse money, and — not to be forgotten — the state also gets a cut. Which meant there would be no repealing the law by the legislature in Frankfort — reformers or no reformers. No bookies. No cheating. All fair and square. And perfectly legal.

    Grinstead fumed, but Winn had colleagues in the judiciary who slapped on an injunction allowing the 1908 Derby to proceed. In succeeding years, the Downs perfected the pari-mutuel system. Within a few years, every track in North and South America switched to the pari-mutuel betting system, and it remains the financial underpinning of the sport today.

    And the Derby? In 1908, those holding a $5 win ticket (the minimum bet) got back a nifty $123.60 when Stone Street crossed the wire first.

    In coming Derbies, Winn reduced the minimum wager to $2, making a Derby bet affordable for almost anyone. The phrase “$2 bettor” was born.
     

    1918
    Old Bones, the “animated hat rack”

    Exterminator turned the 1918 Kentucky Derby — a century ago this spring — into a rags-to-riches story for the ages.

    Before the Derby, Exterminator was
    . . .well, just a plain old horse. A lightly raced gelding who was purchased by big-time horse owner Willis Sharpe Kilmer to be a “work mate” for his stable star, Sun Briar, whom Kilmer was aiming toward Derby glory. But when Sun Briar didn’t train well, Col. Winn urged Kilmer to run Exterminator in the big race. Winn wasn’t a horse expert, but he had seen Exterminator zip along in his trials with Sun Briar. Kilmer’s wife also liked Exterminator, and Kilmer resignedly entered the virtual unknown in the Derby. And he won! Not just won, but looked good doing it, bounding easily over a muddy track to pay a longshot price of $61.20 on a $2 win ticket.

    Well, “looked good” is actually relative. Around the barn, Exterminator was called “Old Bones,” or just “Bones.” A sturdy horse, but coarse. A sportswriter tagged him “the animated hat rack” because you could hang hats all over his bony frame.

    Exterminator went on to win 50 of 99 starts in his eight-year racing career, and more stakes races than any American Thoroughbred up to this day.Exterminator lived to the age of 30, the third-longest-lived Derby winner, and became something of a local celebrity in retirement at his home farm in Binghamton, New York. Mrs. Kilmer threw birthday parties for the gallant gelding, with local kids invited to come out and get to know him.
     

    1928
    Let it rain

    Only Noah could have loved the 1928 Kentucky Derby.

    And Reigh Count, who splashed to victory in a sloppy mud sea. The 1928 Derby was the wettest Run for the Roses ever. After raining all week, the skies unleashed a full three inches more on Derby Day.

    But Reigh Count didn’t care.

    Now, some horses don’t like to get their pretty hooves dirty. Which, of course, is the foundation of the Tippy-Toe Theory, developed by Louisville economist Mac Unger. Bettors can study the post parade on wet tracks and always note a few steeds tippy-toeing their way along, looking for drier spots. These are absolute throw-outs. Won’t win.

    On the other hand, a sharp-eyed bettor might note one that just seems to love the mud. Often it is a big-hooved horse that might enjoy nothing more than angling past one of the tippy-toers to splat down a hoof and cover an opponent in mud. Reigh Count went off as the favorite and won in a field of 22. (That was the most horses ever until 1974, when the 100th Derby attracted 23. Now, the field is capped at 20.)

    Mr. and Mrs. John D. Hertz, who had just gotten into horseracing, owned Reigh Count. Yes, THAT Hertz, who founded a taxi company, with his cab fleet painted yellow — Yellow Cab. Later, he started the rental-car company. The Hertzes also had Count Fleet, who won the 1943 Derby and the Triple Crown — and was the longest-lived Derby winner at 33. Today, Count blood appears in the pedigree of many Derby winners.

    And they can all run in the mud.
     

    1938
    Ladies and gentlemen, meet Plain Ben and Master Eddie

    The year 1938 was the first big splash for two of turfdom’s finest: trainer Ben Jones and jockey Eddie Arcaro. Jones would go on to win more Kentucky Derbies than any other trainer, with six, and Arcaro more than any other rider, with five, later tied by Bill Hartack.

    But in 1938 “Plain Ben” Jones and “The Master” Eddie Arcaro were just starting to make their mark. Arcaro had been looking for a Kentucky Derby horse all winter in Miami and still didn’t have one as he returned to New York, where he was a rising star. Then Jones called and asked him to ride Lawrin, a horse Arcaro didn’t think could possibly beat Stagehand, the Derby favorite from California who had beaten Seabiscuit. Nobody else did either. “Ben kept the wires hot, calling me to say that I mustn’t sell Lawrin short,” Arcaro recalled in his autobiography, I Ride to Win. “I reasoned that if Ben thought he had some sort of chance in the Derby, then maybe I could latch my star to him.” Jones huddled with Arcaro in Louisville. “Eddie, I’m going to tell you one thing you must remember: Any time you decide to make a move on Lawrin in the Derby, he’ll give you an eighth of a mile in 11 seconds.”

    After Jones gave Arcaro a leg up into the saddle, he told the jockey: “Go out there, and hurry back.”

    Arcaro saved his fast eighth-mile for the turn for home, calling on Lawrin to come through along the rail. “Ben Jones was grinning from ear to ear,” Arcaro wrote. “He roared up to me in the winner’s circle. ‘I told you so, I told you so!’

    “Looking back in retrospect, I guess this was my most thrilling experience. After all, you win your first Derby only once.”
     

    1948
    Like driving a Cadillac

    When 1948 rolled around, Arcaro had the mount on Citation, the Calumet Farm star trained by Jones and his son Jimmy.

    Calumet “broke camp” in Florida, sending one string north to New York with Jimmy. Along the way, prepping for the Kentucky Derby, Citation was upset in a roughly run Chesapeake Trial Stakes, at the old Havre de Grace track in Maryland.

    Meanwhile, Ben Jones had another Calumet division, and the top horse of that bunch was Coaltown, who was blossoming like springtime dogwoods. Coaltown won the Blue Grass Stakes in smashing fashion at Keeneland as his final Derby prep. Arcaro wondered if he was on the wrong horse. “Don’t worry, Eddie,” the elder Jones said. “If I thought Coaltown could beat Citation, that’s who you’d be on.”

    In the Derby, Arcaro placed Citation just off Coaltown’s pace, then tapped the accelerator. Citation cruised to the lead and victory. He went on to take the Triple Crown; he won 15 races in a row, and 19 of his 20 starts as a three-year-old — the best such year ever. “Riding Citation,” Arcaro said, “is like driving a Cadillac.”
     

    1958
    Here comes Silky

    Never has there been a horse that came from farther back than Silky Sullivan — at least not one that had a chance to win the Kentucky Derby.

    Silky Sullivan was a horse of the people, with a shiny copper coat and a style that. . .well, Silky didn’t just come from way back to win his races — he came from way, way, WAY back. One time, the colt dropped 40 lengths behind the field — a length being roughly the length of one horse. So he had no chance of winning. But then he came on like a fireball to pass them all. The next race he did it again! When Silky Sullivan came from a mere 29 lengths behind to win the Santa Anita Derby, he earned a trip to Kentucky to be ridden by Bill Shoemaker in the Derby.

    Silky Sullivan was one of three entries in the Derby to go off at odds of 2-1. The big money showed for Calumet’s Tim Tam and Elizabeth Arden’s Jewel’s Reward. But the “$2 bettors” backed Silky Sullivan. More $2 bets were placed on him than on any horse ever up to that time. CBS assigned a special camera just to follow the horse in the Derby, and placed that picture into the corner of the broadcast screen. It was the first split-screen TV image in sports history.

    Alas, Silky never ran out of the split screen, never came on from way, way back. Tim Tam won the ’58 Derby. Silky finished 12th out of 14. But he isn’t lost to history. People still call his way of doing things a “Silky Sullivan finish.”
     

    1968
    Never too late to cash on Dancer’s Image

    The only disqualification of a Kentucky Derby winner came in 1968, when Dancer’s Image was disqualified and placed last — two days after he won the Derby. Not for actions in the race but for a positive test for a prohibited drug, the anti-inflammatory Butazolidin, which is now legal.

    But fans at the track that Derby Day had no notion. The “positive” wasn’t discovered until Sunday, and not reported until Monday. This writer was just a kid then in the infield, and happened to cash a ticket on Dancer’s Image, at odds of 7-2. So did thousands of others. And the betting result stood. Even if Dancer’s Image was disqualified, with second-place finisher Forward Pass registered as the official winner, the betting results had to stand because they’d already paid off on Dancer’s Image.

    In fact, if you still have a ticket on No. 9 in the eighth race at Churchill Downs on May 4, 1968, it is good. Churchill honors all old Derby-winning tickets. Or keep your winning ticket as a once-in-a-lifetime souvenir.
     

    1978
    Affirmed and Alydar

    Affirmed and Alydar — two “A” names that rolled off the tongue and danced across the sports pages in the spring of 1978. Two horses that produced a drama for the ages in the Kentucky Derby and Triple Crown. And a tale that read almost like historical fiction, full of romantic notions of valor and loyalty. Fans made their choices between the two, and never left the orbit of their favorite star.

    Affirmed and Alydar — or Alydar and Affirmed, if you liked it better that way — were almost cousins, if their Thoroughbred pedigrees could be charted as a human family tree. Chestnut-colored branches of a mighty oak line. And from the start, when they first raced against each other as colts in 1977 at summertime Saratoga, their names were ever paired in a rivalry that played out over three seasons of the 1970s, a decade of turf titans and Triple Crown winners.

    But what really put magic into the tale were the people associated with the horses — the human “connections.” There were the patrician owners of Alydar, Admiral Gene and Lucille Markey, the elderly and genteel caretakers of legendary Calumet Farm, which Mrs. Markey had inherited. She named Alydar for her friend, the Islamic prince Aly Khan, whom she called “Aly Darling.”

    From a different world entirely came the American Dream owners of Affirmed, Louis Wolfson and his beautiful wife Patrice. He was a business guy who got tangled up with Richard Nixon and had to do a stretch in the political pen. But he bounced back. Patrice was the princess daughter of Hirsch and Ethel Jacobs, who had built the biggest and best racing stable in New York, giving their champions names like Affectionately and Straight Deal. Nice couples both, the Markeys and the Wolfsons — but never, ever, on the same social-register guest lists.

    The cast of characters got even better as more were introduced. Affirmed’s trainer, Laz Barrera, came off the old Oriental Park track in Havana to lead all trainers in the United States. He spoke a kind of singsong Cuban-English that sounded wonderful around a horse barn. Alydar trainer John Veitch was the well-spoken son of a famous trainer, entrusted to build Calumet Farm back to its former class — and did.

    And, of course, the jockeys. Jorge Velasquez, the No. 1 rider in New York, piloted Alydar. He was challenged by “The Kid,” 18-year-old wonder boy Steve Cauthen, who could ride any horse to the greatest race of its life.

    Both horses were based in the East, but Barrera shipped Affirmed to California to train over the winter for the Kentucky Derby. Veitch prepped Alydar in the East. Winter months wound down to spring weeks, then finally to Derby Day 1978, when the two A-horses came onto the track at Churchill Downs in a field of 11 for the 104th Run for the Roses. A crowd of 131,004 attended on a perfect, sunshiny day in May.

    Onto the track came the No. 2 horse, Affirmed — a light chestnut, not big but sleek. Cauthen wore the Wolfsons’ pink silks. Then Alydar, No. 10, with Velasquez in Calumet’s blue and devil’s red — and just the rider and the horse, no outrider accompanying. Alydar’s coat was darker chestnut, his build more muscular than his rival. He bowed his head, deeply in the solitude of a star on the naked stage.

    The race?

    It wasn’t as close as many expected. Affirmed ran near the lead and stayed on brilliantly down to the wire. Alydar, from farther back, came running but could only close the gap to finish second. “Right at the end of the Derby, Alydar did come with a flurry, but I had the race won,” Cauthen said. Then he smiled, thinking about his own performance. “I think I kept riding three or four strides past the wire. It was the Derby, and I wasn’t taking any chances.”

    The rivalry played out far more closely in photo finishes in the Preakness and Belmont Stakes. But each time Affirmed won (the third Triple Crown that decade, and the last until American Pharoah in 2015), with the Belmont between the two counted as one of the greatest horse races ever run.

    Nobody this writer knows ever switched horses. You were either an Affirmed person or an Alydar person. Probably one could ask around today and still find Alydar people who would be ready to wager one more time if the two were ever again matched in a race.
     

    1988
    Winning Colors' girl power

    Champion filly Winning Colors rolled wire-to-wire to take the 1988 Kentucky Derby under jockey Gary Stevens. It was just the third-ever victory for a female horse in the Derby (the others: Genuine Risk in ’80 and Regret in 1915). Forty Niner, under jockey Pat Day, made a bold challenge through the stretch to get within a neck of the roan-gray filly but couldn’t catch her. “She did it, I didn’t,” Stevens told broadcaster Jim McKay and a worldwide ABC audience as he slowed the big filly after her triumph. “I was just a passenger. She’s incredible.”

    It was the first Kentucky Derby victory for Stevens, who has won three now, and the first of four for trainer D. Wayne Lukas. On the winner’s stand, Lukas recognized his moment. “This one’s for all the guys who ever dreamed it,” he said. “It’s from here to the top of the world.”
     

    1998
    Not that quiet

    Real Quiet is a quiet note now in Derby history, with two decades elapsed since he beat rival Victory Gallop by a nose in the 1998 Kentucky Derby. But for trainer Bob Baffert, the Real Quiet win completed a bold introduction to the Derby. In 1996, Grindstone beat Baffert’s Cavonnier by a head. But Baffert won in ’97 with Silver Charm, and followed that with Real Quiet in 1998. (Real Quiet won the Preakness but lost to Victory Gallop in the Belmont.) Baffert has since won two more Derbies, with War Emblem in 2002 and Triple Crown champion American Pharoah in 2015.
     

    2008
    Nobody loves Big Brown

    Kinetic Imaging is a repository of official Kentucky Derby photography for private purchase and editorial use. Popular winners such as Secretariat and American Pharoah naturally lead the list of most purchased photos. But there is also a clearly least-requested Derby winner, and that’s Big Brown, who won the 2008 Kentucky Derby. “It’s a shame, too,” says collection curator Ann Tatum. “It was a gorgeous Derby Day and the images are just beautiful.”

    A horse can’t help who owns it, but Big Brown came to the 2008 Derby with a load of human baggage that diminished his popularity. The listed owners had been thrown off the stock exchanges for penny-stock fraud. Then word got out that the horse’s real owner was a shadowy figure at an offshore gambling site. The trainer, too, arrived in Louisville with a long list of racing-medication infractions. Later, he was handed a 10-year suspension in New York that applies to every track in North America.

    It’s too bad for the horse, though. His original owner gave the horse the name Big Brown, thinking of the UPS trucks at his business. That could have made a nice story in Louisville.

    And we’d be remiss not to include Eight Belles in a story about Derby years ending in “8.”  The lone filly in a 20-horse field, Eight Belles charged to a second-place finish behind Big Brown, only to collapse just beyond the wire and break both of her front ankles. She was euthanized on the track, and many in the crowd of nearly 158,000 teared up at the sight. Here we are ten years later, another “8” year. Let’s hope for something extraordinary and memorable that will only bring smiles once 2028 rolls around.

    This originally appeared in the April 2018 issue of Louisville Magazine. To subscribe to Louisville Magazineclick here. To find us on newsstands, click here.

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