horses became a routine hazard of pedestrian life; on at least one occasion races were run concurrently, in opposite directions, on the same road. In 1793, terrorized locals finally banned street racing. Undaunted, horsemen built a series of racetracks, running horses in sets of marathon heats. Under this system Kentucky racing and breeding flourished for decades. But the Civil War brought armies that ransacked stud farms and destroyed tracks. By 1872, Louisville’s last track had failed.

Salvation came in the guise of a former bank teller named Meriwether Lewis Clark, Jr. A grandson of the explorer William Clark, M. L. Clark was an avid racegoer who was distressed over the failure of Kentucky tracks. In 1872, at the age of twenty-six, he set off on a tour of Europe, scrutinizing the thriving tracks abroad in search of lessons on reviving Kentucky racing. Britain proved the best teacher. The nation had abandoned endurance races and heats in favor of single-event, shorter contests. Its Epsom Derby had grown into England’s racing championship.

Upon his return Clark presented an ambitious plan to Louisville’s gentry: Build an opulent track, create a championship race on the model of Epsom, cater to high-society racegoers, and the world would beat a path to Kentucky. The marquee event, the Kentucky Derby, would be restricted to elite three-year-old horses running a single mile-anda-half contest. The idea appealed to 320 Louisvillians, who put up one hundred dollars each. On eighty acres leased from his uncles (their name would later be given to the track, Churchill Downs), Clark built an extravagant racecourse, then embarked on extensive personal tours of Louisville to cajole citizens into coming to the Derby.

The first Derby Day, May 17, 1875 drew twelve thousand spectators. Jockeys raced around an infield brimming with picnicking fans, and the winners dismounted to snatch ornate silk bags, stuffed with purse money, hanging by the finish line. Ladies, dressed to the nines, were seated in a special section discreetly out of view of betting pools. In Clark’s clubhouse, spectators sipped mint juleps and enjoyed the races from rockers on a veranda while Strauss waltzes played.

These pampered racegoers were treated to a race whose unpredictability, drama, and display of superb horsemanship set the standard for the Derby. The favorite was Chesapeake, a come-from-behinder trained by the profoundly gifted Ansel Williamson, a former slave. To ensure that the front-runners would exhaust themselves early in the race, Williamson had honed the speed of Chesapeake’s stablemate, Aristides, then entered him in the Derby as a rabbit. The strategy worked, but not as Williamson anticipated. Aristides set a blistering pace, fought off his challengers, then was eased up to wait for his stablemate. But Chesapeake, compromised by a poor start, never came. Remarkably, Aristides had something left. Urged on again, he repelled the closers and won. His time was an American record, and the Derby was off to a rousing start.

For the next several years, the Derby was a

success, attracting huge crowds and the nation’s best horses. Clark absorbed himself in designing dazzling fetes for his wealthy patrons, and his track became the place to be for high society. The moneyed set warmed to the attention, but at a cost. Clark reportedly focused entirely on his well-heeled patrons, leaving details of track operations to incompetent subordinates. Churchill Downs never turned a profit.

Then, in 1886, a petty squabble nearly ended the Derby. It began when bookmakers who refused to pay the track their operating fees were locked out on Derby Day. James Ben Ali Haggin, a high-rolling New York gambler and influential owner, had brought a huge string of horses to Churchill Downs for the season. Though he was upset at the absence of bookmaking, he ran his namesake, Ben Ali, in the Derby and watched him win it. He then announced that if bookies didn’t return, he would pack up his horses and leave. The threat carried considerable weight; without Haggin’s fine horses the 1886 Churchill Downs season, as well as the 1887 Derby, would be seriously diminished. Within hours crisis seemed to be averted when the bookies reached a settlement with the track. But the triumph was undercut by a track official, who told listeners in no uncertain terms where Haggin could go. Word of the statement reached Haggin that night. By dawn his barn was empty.

Haggin meant business. Back in New York, he persuaded all the Eastern horsemen, whose runners dominated racing, to join a boycott of Churchill Downs. The impact was staggering. Kentucky’s horses were not yet the cream of the industry they would later become, and they couldn’t carry the track or the Derby. Interest in the race plummeted, and its fields shrank to three or four woeful entries. Clark struggled on without pay, covering thousands of dollars in debts out of his own pocket. But Churchill Downs drifted deep into the red, and by early 1894, the Louisville Commercial was referring to the Derby as “a contest of dogs.” That August the track went bankrupt, and Clark, utterly despondent, left its helm. He never recovered. Five years later he was found dead in a hotel room, the pistol still in his hand.

A group of investors obtained Churchill Downs and renovated it with a new grandstand featuring the now-signature twin spires. The race distance was cut to a mile and a quarter—a particularly formidable distance requiring both speed and stamina—and the track began draping the winner in roses, a tradition that later inspired the race’s nickname, Run for the Roses. But the boycott continued. Worse, management slashed purses. Trainers took their better animals away in search of bigger purses, attendance sank further, and Derby fields remained tiny and poor. In 1902, the managers gave up and looked for someone on whom to dump their white elephant.

The man they found was an unlikely deliverer, a merchant tailor named Col.

Matt J. Winn. At the age of thirteen, upon witnessing Aristides’ Derby triumph from his father’s grocery wagon, Winn had been smitten with the race and had seen every running since. He had no experience managing a track, but he was endowed with irresistible charm and uncanny business sense. Taking over as vice president and later as general manager, Winn began by making personal appeals to Louisvillians who had once frequented the track, offering them choice seats at the 1903 Derby. The campaign worked. Erstwhile fans brought loads of friends to the race, and Winn entertained them so well that they kept coming back. For the first time Churchill Downs made a profit. It continued to run in the black in succeeding years, and though the Derby couldn’t seem to draw more than six modest, locally based horses, things looked promising.

Soon, though, the race was in trouble again. Just after the turn of the century, the nation was swept up in an antigambling “reform” movement. In 1907 reformers won the Louisville mayorship and promptly banned bookmaking, the only form of wagering at Churchill Downs. Winn was left with two alternatives: antiquated “auction pool” wagering, which excluded bettors of small wagers, and the French pari-mutuel machine, which automatically calculated the winners’ rewards based on what they had wagered, dividing up the total pool of money bet. The latter seemed ideal, eliminating the famous corruption of bookmaking while allowing bets as low as one dollar. But pari-mutuels had had a disappointing history in America; Clark had imported four machines, and like other track operators, he had failed to lure bettors to them. Still, pari-mutuels were the better choice, so Winn opted to use them. City Hall responded by dredging up an ancient law banning machine betting. Winn was left only with auction pools, which would surely be banned also. The Derby and Churchill Downs appeared doomed.

Pondering the looming failure of their race, Winn and the track president, Charlie Grainger, began to wonder how Clark had gained legal authority to use pari-mutuels. They scoured lawbooks and found the answer. Buried deep in the legal code was an amendment excluding pari-mutuels from the antimachine gambling law. “We were jubilant,” Winn later wrote. But with little time before the Derby, he had no pari-mutuels to use. Importation would take too long, and no one knew what had become of Clark’s four machines. Winn recruited an army of Louisvillians to hunt for them; he suspected that City Hall was also searching for the pari-mutuels in hopes of destroying them. Pro-racing hunters found all four, and Winn persuaded a New York track to ship in two abandoned machines. Every one of them was in deplorable condition. Mechanics, working frantically, rebuilt all six.

The crisis still wasn’t over. Learning that Winn had obtained pari-mutuels, City Hall vowed to send the police in to arrest everyone connected to wagering. Winn took the issue to court and won. The Derby was on. Ironically, the

clash boosted Derby attendance by flooding the city with publicity. Buoyed by the attention and Winn’s pro- motional fliers, the machines were immensely popular; wagering on the 1908 Derby was five times greater than in 1907. “The machines,” Winn wrote, “had saved racing in Kentucky ...”

Reformism was soon dead, but the Derby was still no more than a local function. Winn needed a headliner, something to break into the national consciousness. In 1913, his wish was answered when an impossible long shot named Donerail dropped from out of the clouds to win the Derby in what remains the race’s greatest shocker. Donerail paid a stunning $184.90 for a $2.00 bet, landing the race in the national news. Seizing the opportunity, Winn traveled back East and turned on the charm, trying to end the quartercentury boycott of his race. In 1915 came the breakthrough: Winn convinced the influential New Yorker Harry Payne Whitney to run his mighty filly Regret in the Derby. Regret simply annihilated the boys, becoming the first filly to win the race. Whitney was euphoric. “I do not care if she never wins another race, or if she never starts in another race,” he said. “She has won the greatest race in America, and I am satisfied.”

With that statement, “the Derby was thus ‘made’ as an American institution,” wrote Winn. Regret “put us over the top.”

The boycott was over, and the Derby prospered, drawing as many as 20 or more world-class horses each year. Winn began courting influential print, and later radio, journalists, treating them to every possible luxury during Derby Week. Drawn by the glowing news coverage, Americans focused on the race each May; by the mid-1920s eighty thousand people were cramming into the track for the race. In 1925 the Derby’s first radio broadcast drew five or six million listeners, an audience estimated to be the largest yet for any broadcast in the history of the medium. By 1931, half the nation was tuning in for the race. With the onset of the Depression, ten state legislatures, desperate for revenue, authorized pari-mutuel betting in order to tax the winnings. Racing quickly became the most heavily attended sport in the nation, and the Derby became its crowning moment.

As the Derby basked in its newfound fame, two other spring races for top three-year-olds, New York’s Belmont Stakes and Maryland’s Preakness Stakes, were also eniovine success. In 1935. when a colt named Omaha achieved the fantastically difficult task of winning all three, writer Charlie Hatton coined the term Triple Crown . What is arguably the most formidable challenge in sports had been born. The two horses that had won all three in earlier years, Sir Barton and Gallant Fox, were retroactively named Triple Crown winners. In 1937 War Admiral became the fourth. No longer an event that would have to stand alone, the Derby now marked the start of a nationally celebrated, weeks-long rite

of spring. Winn’s race, hamstrung for so long by political and financial problems, would from now on be defined solely by its spectacular competitors.

In 1941 came Whirlaway. The chestnut horse with the exceptionally long tail was the most eccentric personality to make his mark on the Derby. He was, said his trainer Ben Jones, as “nervous as a cat in a room full of rocking chairs.” He was known to make sudden ninety-degree turns toward the crowd in mid-race, zigzag drunkenly, and run whole races along the outside rail, losing massive amounts of ground as he blew past the grandstand inches from amazed fans. (He often won anyway.) Even his jockey, Eddie Arcaro, admitted that he was terrified of the colt. Yet even as he invariably took the scenic route around the track, Whirlaway could unleash a closing rally that was absolutely scorching. Arcaro described him as a “blinding tornado. . . . What a horse! What a horse!”

But Jones knew that Whirlaway would lose the Derby if he kept careening all over the course. He tried everything to reform him; during one workout, Jones ordered an intimidated Arcaro to charge Whirlaway through a razor-thin gap between a standing pony and the rail. Before the Derby, Jones walked Whirlaway along the inside rail, then took him to the outer rail in hopes of satisfying his insatiable curiosity about spectators. Then, minutes before the race, Jones cut away the left eye cup on the colt’s blinkers, hoping that opening the horse’s vision to the inside would help him resist the urge to buzz the crowd.

Leaving the gate, Whirlaway and Arcaro dropped behind the field. On the far turn a hole leading into the pack opened before them. Arcaro had a weighty decision to make: dive into the hole and risk being blocked while moving at terrific speed, or lose ground circling the pack and face the possibility that Whirlaway would pay the crowd a visit. Arcaro chose the former and charged Whirlaway into the gap. In a moment of supreme drama, Whirlaway darted into the back of the pack and disappeared from view. A second later he came roaring out the other side, pouncing forward with such force that Arcaro nearly tumbled backward out of the saddle. ”... I felt as if I were flying through the air,” the jockey told Peter Chew, author of the splendid The Kentucky Derby: The First 100 Years. Whirlaway hit the lead and kept rolling, arrow straight, to an eight-length victory. His record time of 2:012/5 would stand for twenty-one years. Whirlaway went on to win the Triple Crown.

In his 80s, but vigorous as ever, Matt Winn guided the Derby through the 1940s. From an infield tower, he watched

a remarkable procession of gifted horses, including eventual Triple Crown winners Count Fleet and Assault, sail to Derby victories. In 1948, with the emphatic victory of soon-to-be Triple Crown champ Citation, he hosted his greatest runner yet. Winn’s job was done. In 1949, the man who compared his seventy-five Derbies with rosary beads, “always before me, always vivid, with every detail silhouetted in the light of the vanished years,” died.

With Winn’s death the Derby reached an odd turning point. Year after year great horses had paraded through Louisville and, after clean racing trips, emerged as champions. A single generation had seen eight horses sweep the Triple Crown; one arrived every few years with clockwork regularity. But in the 1950s the unexpected became the rule. It began in 1953, when the wildly popular, wonderfully telegenic Native Dancer, the Derby’s first television star, was bumped, checked, and blocked into a heartbreaking head loss, the only race in which he was ever beaten. The unthinkable recurred in 1955, when the seemingly unbeatable Nashua was hoodwinked by Swaps, a California speedball whose owner slept in a stall to be near him. Two years later the unexpected gave way to the truly bizarre. A few days before the Derby, the owner of the great Gallant Man dreamed that he saw his colt leading the Derby down the stretch. The dream then became a nightmare. Just before the wire Gallant Man’s jockey inexplicably pulled up, slowing the horse and costing him the race. Sure enough, on Derby Day, Gallant Man rocketed down the Derby stretch and seized the lead, looking like a winner until the jockey, Bill Shoemaker, misjudged the 16th pole as the finish, pulled up and stopped urging his mount momentarily, and lost by a nose. The Derby’s era of the peculiar was far from over.

In April 1971, a colt named Canonero II stepped aboard a cargo plane in Caracas, en route to the Derby. The race he was set to contest was in turmoil. In 1968 the Derby winner Dancer’s Image had been disqualified after traces of Butazolidin, a therapeutic, non-performance-affecting antiinflammatory drug similar to aspirin, were found in his system. Many suspected that outsiders seeking to discredit the horse’s owner, Peter Fuller, had tampered with his horse; Fuller had been buried in racist hate mail after donating the colt’s earnings in the Governor’s Gold Cup to Coretta King. But no one ever determined who gave the colt the drug, which, most frustratingly, was later legalized. As Canonero II embarked for Miami on the first leg of his journey, the Derby remained mired in a wrenching court battle as a devastated Fuller fought in vain for vindication for his horse, who was characterized as “doped” by the press. A pall hung over the Derby; the race needed redemption.

Canonero IPs

only escorts were the teenage son of the owner Pedro Baptista and several crates of ducks and chickens. No one in the United States had ever heard of him; when a representative called to nominate him to the Triple Crown, the official Chick Lang thought he was kidding. He had good reason. Thanks to an ugly, backward-bending foreleg, the colt had been given away, then sold to a Venezuelan for a pittance, then given away again, a questionable wedding gift to the Venezuelan’s son-in-law. He had been shipped all over the Western Hemisphere to run in cheap races, logging enough air time, wrote Joseph Challmes in The Preakness: A History , “to qualify as a pilot.” But the colt, named for Latin American street musicians, had a taste for distance running, and the Derby’s mile and a quarter looked about right.

Canonero IFs first flight turned back when the plane’s engine caught fire. The second returned with mechanical problems. When he finally got to Miami, he was at wit’s end from the incessant clucking of his fellow passengers. Someone had forgotten the customs papers, so he spent four days locked in quarantine. After clearing customs, he was loaded into a van, which broke down. By the time he finally made it to the track, Canonero II had lost seventy to eighty pounds. His trainer, Juan Arias, feared he would have to be scratched. He .sent the colt out to exercise with a rope around his neck and a boy riding him bareback, to the ridicule of onlookers. Canonero II clocked preposterously slow times. But, as Derby Day approached, the colt began coming around. Arias decided to run him.

Leaving the starting gate, Canonero II dropped back to 16th and was at 18th by the half-mile pole. Everybody expected him to stay there. But what hadn’t occurred to anyone was that in Venezuela the colt had been racing in thin air three thousand feet above sea level; in the oxygen-rich Kentucky air, he had virtually infinite stamina. As the front-runners faded, Canonero II was just getting going. “There was no such animal at the head of the stretch,” Lang told Challmes. “You couldn’t find him. He was back there sucking up all the grit. ... It looked like 20 Mule Team Borax coming down the stretch. And then— pffsst ,out like a grapefruit seed—here he came.” Closing in, the Venezuelan disgrace caught the field, then buried it behind him. The crowd was dead silent. In the press box a reporter muttered, “Canonero II? Who the hell was Canonero the first?” As the horse loped back to the grandstand, his jockey, Gustavo Avila, began waving his arms wildly, and the crowd finally raised a cheer. Down in Venezuela his owner received a call from someone telling him he had won. “That’s a sick joke!” Baptista shouted, hanging up. When more calls came in, he realized what his colt had done. In Caracas, they danced and

sang for Canonero II all night long.

The “Caracas Cannonball” won the Preakness and drew a cult following, but like every Derby winner in the long, strange years since Citation, he failed to win the Triple Crown. Pressure was building for a superstar to emerge. Racine, and the Derby, needed a Triple Crown winner, but after twenty-five years of mishaps, scandal, outrageous fortune, and nearmisses, many racegoers believed they would never see another one.

Then, on May 5, 1973, a sleek black colt named Sham leaned out of the final turn in the lead in the ninety-ninth Kentucky Derby. The front-runners were finished, and though he had blood spraying from his chin after ripping two teeth loose in the starting gate, Sham was staging an epic performance. When he hit the wire seconds later, he would register a time fast enough to win every Derby in history with ease.

But Sham lost.

As he shot to the lead, an enormous red colt hurtled up behind him, running with fearsome, predatory lunges. He may have been the most awesome racing engine ever crafted. In his massive chest, which measured well over six feet around, beat a heart weighing some twenty-two pounds; at nearly three times normal size, it was the largest heart known to equine medicine. He pushed his 1,160pound body over the earth with a twenty-four-foot threeinch stride that, when analyzed by Professor George W. Pratt at MIT, proved to be the most efficient ever studied. According to Pratt, the colt’s race times were so fast that at the breed’s rate of improvement, elite horses wouldn’t catch up to him until 2064, ninety-one years later. He ran with a geometry of straight lines, precise turns, relentless, unflagging rhythm; the race caller Chick Anderson would call him “a tremendous machine.” His name was Secretariat.

He closed on Sham with a terrible inevitability, seeming to feed off of each grueling furlong; he was running each quarter-mile faster than the one before, an unprecedented feat. Sham fought like a tiger; Secretariat overwhelmed him. He hit the wire traveling at more than fifty-seven feet per second, halting the clock at l:59 2/5, a Derby time that has never been approached, before or since.

The spell that had hung over the Derby had been shattered. Secretariat, with Sham pushing him all the way, won the Triple Crown, a feat repeated by Seattle Slew in 1977 and Affirmed in 1978.

After more than a century, it seemed that the Derby had displayed to the fullest every virtue of the communion between horses and men and that runnings _ to follow would not find a fresh answer to the glories of the past. But the genius of the Derby is that it reaches for the hard, hidden places in its competitors and invariably finds there something singular, something to surprise and dazzle and astonish. Thus it was in 1987.

In the starting gate,

the jockey Chris McCarron crouched low over the neck of an exuberant colt named Alysheba, bracing himself for a race that had become his life’s obsession. He had no idea that the contest about to unfold would be one of the roughest major races in history. Shocked spectators would call the race chilling. One jockey would liken it to a rodeo, while another would be too shaken to talk about it. For McCarron and Alysheba, it would be a two-minute horror show.

It began the instant the gate doors crashed open. From stall three, McCarron gunned Alysheba forward with three other colts, trying to gain forward position. In a chaotic headlong charge the horses to their outside angled inward, compressing them into a high-speed bottleneck. Alysheba was slammed into the horse to his left, which shouldered another horse into the rail. Ahead of them horses crushed inward, their legs nearly tangling with the horses behind. For a dozen strides Alysheba and three rivals were pinned together between seven tons of horseflesh and an unforgiving strip of metal. There was nowhere to go but back. McCarron snatched up the reins. Alysheba threw his head up in protest, knocking McCarron backward. Regaining his balance, the jockey hauled his colt out of the vise and dropped back to fourteenth. Though he had narrowly escaped falling, McCarron now found himself straggling ten lengths behind the leaders. His game plan, and possibly his chance of winning, was dashed just seconds into the race.

Hugging the rail into the first turn, McCarron watched the pack of horses ahead surge inward again. The horses to the outside cut in much too fast, causing another chainreaction collision. A few feet in front of him, McCarron remembers, “there were about three horses where there was room for one.” One of them, a colt named War, was rammed into the rail. Desperate to escape, he lunged up and hung halfway over the barrier for an awful moment, skidding and thrashing, a millimeter from flipping into the infield.

Thinking a pileup was coming, McCarron sacrificed his ground-saving rail position and yanked AIysheba out from behind War, bouncing hard off another horse but staying on his feet. Safely outside as the horses to his inside recovered, McCarron waited until the far turn. There he turned Alysheba loose. The response was electrifying; while nearly every other horse that had been buffeted in the traffic jams was spitting out his bit and retreating, Alysheba was crying out to run. He swooped around the field, and turning into the stretch, McCarron recalls, “I had one horse ahead of me and I thought I had a dynamite chance to win.”

That horse was Bet Twice, and he was laboring, his stride deteriorating into lazy, irregular footfalls. Alysheba drove at him from the grandstand side,

his nose lapping Bet Twice’s tail. Suddenly Bet Twice ducked sharply outward. McCarron saw the enormous churning hindquarters veering into him and knew what was coming. Alysheba reached out just as Bet Twice’s hind legs pushed out behind him. Jockeys say there is a bright, crisp ring as metal-shod hooves connect, or “clip,” an incongruously cheery portent of the wreck that is likely to follow. McCarron can’t remember if he heard it. But as Bet Twice lurched over, he kicked Alysheba’s forelegs out from under him. Alysheba’s front end dropped like a hammer. McCarron saw his colt’s head and neck fall away as the ground heaved up. His hands, clutching the reins, were jerked forward; with fifteen horses behind him, Alysheba was dragging McCarron into a forty-mile-per-hour somersault. “I thought,” the jockey told Sports Illustrated , “I was gone.”

With a speed of thought and action he credits to the importance of the race, McCarron threw himself backward and gripped the reins in a hammerlock, taking weight off Alysheba’s sinking front end. Alysheba, his knees nearly on the ground, whirled his legs forward in one lithe motion; the colt landed violently on one foreleg, catching himself just in time.

McCarron expected his mount, like virtually everv other horse in his experience, to be intimidated by a mishap that easily could have resulted in horse and rider being trampled to death.

He was wrong. Alysheba pinned his ears and took off after Bet Twice, spoiling for a fight.

Alysheba and McCarron charged down the stretch in oursuit of Bet Twice. Again Bet Twice zigged outward. McCarron swerved his colt out sharply just in time to miss a second collision, then had to dodge right again as Bet Twice veered out a third time. With McCarron shouting him home, Alysheba stretched for the finish. The Kentucky ground shivered with the roar of 140,000 voices as man and animal took the lead and hurled themselves under the wire.

The victor is led over the infield bluegrass, walking down a gantlet of men to the winner’s circle. He treads a path ennobled by Secretariat, Citation, Arcaro, Tones, Regret, and Aristides. His hooves rest on earth cultivated by Winn, shaped by the visions of Clark, touched by Boone. They wreathe his shoulders in a rush of roses and the weight of tradition, his name forever amended with the grand words Derby winner .

“This is the moment, the peak, the pinnacle,” wrote Faulkner. “After this, all is ebb.”