Inspiring the Chase, Part III

(This blog post is the third in a series of four, profiling the first horse to traverse what we now know as the Triple Crown trail. In 1918, War Cloud started in the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes for the first time, inspiring Sir Barton’s run in all three the following year. You can read part one here and part two here.)

In 1917, the Woodlawn Vase, prized trophy with antebellum origins, came into the possession of Colonel E.R. Bradley after his colt Kalitan won the Preakness Stakes. Previous owners had passed the Vase to the next one via whatever race they chose. Thomas Clyde decided to give the Vase to the Maryland Jockey Club, who, in turn, designated the trophy for the Preakness. It was the birth of yet another tradition for Maryland’s most prestigious stakes race. In 1918, the Woodlawn Vase was supposed to go to the winner of the Preakness Stakes, but unique circumstances would see it stay in Maryland rather than traveling home with a winning owner.

Continue reading “Inspiring the Chase, Part III”


Inspiring the Chase, Part II

(This blog post is the second in a series of four, profiling the first horse to traverse what we now know as the Triple Crown trail. In 1918, one horse started in the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes for the first time, inspiring Sir Barton’s run in all three the following year. You can read part one here.)

In 1916, A.K. Macomber sent his imported colt, Star Hawk, to the Kentucky Derby as one of the historic race’s favorites. Not quite a year into his reentry in American racing, Macomber was poised to win his first Kentucky Derby, tantalizingly close to one of those dream moments all horse owners seek. Instead, jockey Johnny Loftus on a colt named George Smith held off the driving Star Hawk in the stretch to win the Derby for owner John Sanford. Coming that close to winning the Kentucky Derby prompted Macomber to search his growing stable for another chance at the roses. He tapped War Cloud to carry the red and white Macomber stripes in the 1918 Kentucky Derby.

Continue reading “Inspiring the Chase, Part II”

Inspiring the Chase, Part I

(This blog post is the first in a series of four, profiling the first horse to traverse what we now know as the Triple Crown trail. In 1918, one horse started in the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes for the first time, inspiring Sir Barton’s run in all three the following year.)

After dominating victories in the Kentucky Derby and Preakness Stakes, Sir Barton won the Belmont Stakes on June 11, 1919, sealing America’s first Triple Crown. Sir Barton was the first to win all three, but he was not the first to run in all three classics. That distinction belongs to War Cloud, a British-bred colt owned by adventurer and financier turned breeder and owner Abraham Kingsley (A. K.) Macomber. In 1918, War Cloud’s trip through what we now know as the Triple Crown trail was a pursuit fueled by money and prestige, a chase that caught the eye of the racing industry, including Commander Ross and H.G. Bedwell.

A Little History

Prior to War Cloud, only three horses – Vagabond (1876), Hindus (1900), and Norse King (1915) – had started in the Kentucky Derby and then shipped to Baltimore (or New York, in Hindus’ case) to run in the Preakness Stakes. The Preakness and Belmont Stakes count 27 horses that were starters in both prior to 1918, aided in part by the Preakness was run in the New York area between 1890 and 1908, once at Morris Park and then at Gravesend. Apart from the races’ inconsistent scheduling, the distances between each city made owners and trainers reluctant to ship their horses – until 1918.

Instead, the Triple Crown, this now-essential test of horses, came about because of two important elements: money and prestige. A.K. Macomber, already wealthy in his own right, may not have chased the money, but he did desire the prestige that came with running his horses in the sport’s most prestigious races. And, like Sir Barton’s owner Commander Ross, he was not afraid to use his considerable fortune to make his mark on the sport forever.


Continue reading “Inspiring the Chase, Part I”

A Writer’s Ode

I first stepped onto a racetrack at age 12, thanks to my aunt Betty indulging my burgeoning interest in the sport with a trip to the Birmingham Race Course. I don’t remember much about that trip — outside of the grizzled old gamblers who thought I was some sort of betting prodigy — but I do remember the Daily Racing Forms scattered throughout the track, as ubiquitous as the discarded losing tickets. Every visit to the racetrack means a trip to the newsstand to grab the Form and consult its pages before I hand over my money for any bet, whether it’s the Preakness or the third race on a weekday at Keeneland. So, today, on the 123rd birthday of the Form, I wanted to explore the impact of this historic publication and the institution that has endeavored to preserve it.

Four years ago, the Sir Barton Project started as an idea that led to a search that then turned into the hubris necessary to think that one is the right person to take that idea to fruition. From high school to college to graduate school, I learned how to research topics of all kinds, from high literary questions to the mundane inquiries about daily tasks. When I undertook the challenging task of bringing Sir Barton’s complete story to print, I knew that the place I needed to go to find his story and to bring its scattered pieces together lay in one place: Kentucky. More specifically, the Keeneland Library and the Daily Racing Form archive.

I have spent many hours in the stacks at Keeneland, wanting to break into song at the richness of their collections. How many times have I heard “Have you been to the Keeneland Library?” as I inquire with other places about resources I’m trying to find? The Library is the first place and the best place to go whenever I need an article, a photograph, or a hard-to-find book.

In addition, the Library gave writers and researchers the most thorough collection of the essential publication for racing across history, the Daily Racing Form archive. My time on the DRF archive, searching through form charts, workout reports, and articles for horses from Sir Barton to Man o’ War to War Cloud, would probably total in years at this point. This book about Sir Barton came to be because I was able to trace the milestones of his career from the first mentions of him as a yearling up to his death in 1937 and beyond. The efforts of Becky Ryder and every person who worked on this archive have been essential to projects like mine. I cannot thank them for this resource enough.

Happy Birthday to you, Daily Racing Form, first published on this day in 1894! Thank you for bringing racing to your readers day after day for 123 years. You hold the history of racing within your pages each day, preserving it for generations of racing fans. Many thanks to the Keeneland Library as well for making the DRF‘s past available to the present and future of thoroughbred racing.

The Big Three Face Off — Again

2017_TraversThis Saturday, Kentucky Derby winner Always Dreaming, Preakness Stakes winner Cloud Computing, and Belmont Stakes winner Tapwrit will square off in the mile-and-a-quarter Travers Stakes at Saratoga. Thirty-five years earlier, in 1982, the three classic winners — Gato Del Sol, Aloma’s Ruler, and Conquistador Cielo — all met in the Travers as well, but Runaway Groom, winner of the Prince of Wales Stakes in Canada, surprised them all in the stretch to win. In 1918, the Kentucky Derby, the Preakness, and the Belmont winners all faced off in the Travers Stakes at Saratoga, also with a surprising result.

Sun Briar on the rail, with Exterminator on the outside.

Early on in 1918, Sun Briar had been one of the leading two-year-olds from the previous year looking to dominate again in his three-year-old season. Along with War Cloud, he was one of the early favorites for the Kentucky Derby, but an injury that spring meant that trainer Henry McDaniel would not have the colt ready for the Run for the Roses. Owner Willis Sharpe Kilmer was in danger of going without a Derby horse until he picked up the gangly gelding Exterminator in the weeks leading up to the race. Exterminator surprised everyone by winning the Kentucky Derby. Now Kilmer had two great horses in his barn: Exterminator and Sun Briar, but the owner still preferred his bay champion over the chestnut newcomer.

Continue reading “The Big Three Face Off — Again”

His Name Was Johnny

He was born John Patrick Loftus in Chicago, Illinois, the son of parents who had immigrated to the United States from Ireland. His father was an engineer; his mother birthed five sons: John, Martin, David, Frank, and Robert. Nothing in his background made horses a clear choice for young Johnny, but, nevertheless, he gravitated toward the racing life and made it his own.


When Johnny came of age, he was attracted to horses just as the racetracks around him closed, felled by the movement against gambling in the United States. Unscrupulous gamblers and the resultant scandals led to a wave of anti-gambling legislation in the United States. By the time young Johnny Loftus rode in his first race in 1909, the racing world within the vast expanse of American soil was shrinking down to just Kentucky and Maryland, with limited racing in far-flung corners like Jacksonville, Florida, where young Mr. Loftus rode his first race. He finished last.

Not an auspicious start to his career, but the young Loftus was determined to make a go of it. He loved horses, inhaled them even, content to sleep in their stalls and learn everything he could about them. Horses responded to him; he learned to become a master of pace, knowing how fast the horses around him were going and judging when to move his own mount in response. The skills he acquired in his years of traveling from place to place in search of mounts netted him wins in prestigious races like the Kentucky Derby, the Preakness Stakes, the Travers Stakes, and more. He rode the big name horses of the day: Exterminator, Regret, War Cloud, and more.

His biggest problem wasn’t getting the mounts, though; it was his physique. Loftus teetered on the brink of unemployment with every pound. His powerful legs might have helped him balance on the brief width of leather beneath him, but those muscles were also weight that he couldn’t shed. Johnny tried to ride at 110 pounds or less; often, he couldn’t manage to get below 112. A brief stint in Europe and the heavier weights horses carried there gave him some respite from the struggle, but, when he returned to the United States, the fight was on again. He could never escape the ravages of weight, but it wouldn’t stop his ascendency either. Johnny Loftus was one of the elite riders of his day, and, as a master of pace; his services would be needed for one Commander JKL Ross to win the 1919 Kentucky Derby and his bet with Arnold Rothstein.


The 1919 Kentucky Derby showed just how tough a fight it was for Loftus to maintain his weight. Sir Barton was assigned 110 pounds, the beneficiary of a twelve-pound break in weight because of his maiden status. His jockey Johnny had a body that rebelled against such light imposts; Sir Barton carried 112.5 pounds because Loftus’s physique, already haggard and sunken from the battles with weight, refused to shed the difference. The extra weight meant little to Commander Ross; Loftus was still one of the best jockeys in the country. He piloted Sir Barton exactly as planned, sending the speedy colt to the front with unexpected results: rather than burning off the speed horses and giving way to his stablemate Billy Kelly, Sir Barton won a wire-to-wire Kentucky Derby in the slop. The Derby winner’s circle photo shows Loftus looking lean and hungry, unable to crack a smile despite the fact that he had just won his second Kentucky Derby. That struggle with weight might mean that Loftus would ride a pound or so overweight, but his skills and record were such that it never seemed to matter to his employers. Johnny had more than his fair share of winners, with 580 winners from 2,449 mounts in his ten-year career.

In his career, Loftus won most of the major American stakes races, including the classics and, of course, the first Triple Crown. He rode Man O’War, Sir Barton, War Cloud, Regret, and many more top horses of that era. The first part of the twentieth century was a time when jockeys had no union and operated with contracts that could be bought and sold like the horses they rode, but Loftus was among the elite, riding for the top owners of the day, including A.K. Macomber, Commander JKL Ross, H.P. Whitney, and Samuel Riddle. For all of the laurels he collected, though, he has the misfortune of one black mark on his record: the 1919 Sanford Memorial Stakes.


One of the first skills that jockeys in this era had to learn was how to balance the plethora of sensory inputs that were the starting barrier for any race. Long before the starting gate became a reality, horses stood in front of a stretched white fabric webbing before them which marked the starting line. On a stand on the other side of the rail was the starter, a man whose goal was to get all of the horses standing still and facing forward in line at the same time and then releasing them. Assistant starters, usually strapping men with horse whips, stood behind them, helping to get anyone unruly into line. Jockeys needed to have their own mounts in position while also watching for the starter to pull the lever and spring the barrier to start the race and do all of this with any number of other horses and jockeys trying to do the same thing. Kicks and shouts and false starts were all trials to be borne for the chance at the perfect start. Loftus mastered this skill as did many of the era’s greatest jockeys, all angling for the flying start that would catch their mounts already in stride as the barrier gave way to the action.

August 13, 1919 saw Saratoga without their usual starter, Mars Cassidy. Loftus was well aware of Cassidy’s tells, but was not at all familiar with his replacement Charles Pettingill. Pettingill, who had once been a starter before becoming a judge, was known for the seeming inability to do his job; a number of the races on the Saratoga card that day had terrible starts, with Pettingill unable to keep things tidy and orderly. Then came the Sanford Memorial Stakes.

Laden with 130 pounds, Man O’War was one of the high weights in the race, Golden Broom the other, also with 130 pounds. Loftus’s instructions were to let Golden Broom set the pace and then to move when he tired, rather than running on the front. The race was only six furlongs with every other horse massive underdogs next to the strapping Big Red. All Johnny had to do was avoid trouble and surely this start would end as all of the others would, with Red coming home first. Pettingill’s inability to get the horses at the start under control meant that Loftus, trying to get Man O’War back into position for a fresh start, wasn’t ready for the lever’s fall. The field got a jump on him and the greatest horse of the 20th century was nearly left at the post.

Doing his best to follow instructions, Johnny kept his mount behind the front runners, but soon realized that he was boxed in. Upset kept Golden Broom close to the rail, preventing him from squeezing through when the latter might bear out on the turn. Next to him was Donnaconna, just back on his flank. If he took Man O’War to the outside, going around all of this horseflesh, he would expend quite a bit of energy, that 130 pounds telling on any mortal body. If they stayed where they were, they would have to wait for an opportunity or create it. Loftus tried to create it, shouting for room to come through. Neither Golden Broom nor Upset gave way. The box was closing quickly as the ground between them and the finish line grew smaller and smaller.

Finally, Golden Broom gave way, the 130-pound impost too much. He fell back, leaving only one horse in front, and finally Loftus was able to swing Big Red to the outside. With only a furlong left, Loftus unleashed Man O’War, urging him to make up ground. Willie Knapp, Upset’s jockey, did the same on his mount and, though the gap between the two was starting to close, the bare furlong turned in mere yards and then only feet for Man O’War to close the gap and then eclipse Upset. But Upset carried only 115 pounds to Man O’War’s 130 pounds, enough to make a difference. The crazy start plus the rough trip meant that despite every inch of the twenty-eight-foot stride that Man O’War possessed was not enough to catch the elusive Upset. They crossed the finish line, with the aptly named Upset a bare half-length in front. In the next couple of strides, Man O’War had caught the upstart, but it was too little too late.

It would be Man O’War’s only loss. It would contribute to Loftus’s undoing.


Despite going on to win three more starts on Man O’War that year, Johnny’s legacy became forever tied to the misfortunes that resulted in Big Red’s only loss. He mysteriously lost his jockey’s license the following year and was never able to regain it; he applied for a trainer’s license, though, and was granted that immediately. He stayed in the game as long as he could, training stakes winners for prominent owners, but, when he had a streak of bad luck, he gave up the racing game for something far calmer and less risky: carpentry. He died in 1976, far away from the bugle’s call and the tiny square of leather that had been his office for so long.

In the end, John Patrick Loftus was remembered less for the classics he won and the Triple Crown he helped to pioneer and more for the bad start and even worse racing luck that plagued Man O’War on that fateful day, the one black mark on Big Red’s career that haunted the jockey, not the horse, for years to come.

His name was Johnny, an Irish boy who rode horses and became one of the era’s best and brightest jockeys. He was one of the First, the right pilot for the right horse at the moment when history was made.

Many great & glorious thanks to Dorothy Ours & her book on Man O’War for giving me inspiration as well as serving as a wonderful source on Johnny Loftus & many other topics.

Coming Back After a Triple Crown

The term ‘Triple Crown’ was coined in the decade after Sir Barton’s springtime domination of the classics, which, at the time, had yet to solidify their reputation as such. Though War Cloud completed the triple first, showing that making the trip from Louisville to Baltimore to New York was worth the trouble, the money that Sir Barton amassed in purses in his pursuit of the first Triple Crown is really what set the stage for the classics and the Triple Crown to become the gold standard for thoroughbreds. The chestnut son of Star Shoot* completed the triple in only 32 days — throwing in the Withers in between — a schedule that no trainer today would dream of following. By the time he got to the one-mile Dwyer in early July, Sir Barton was sore and tired and his performance in that race showed it. He earned a much-deserved long layoff, until September 11th, 1919, when he ran in the Hip Hip Hooray Purse.


When American Pharoah came back from his Triple Crown triumph in 2015, his owners chose the Haskell Invitational, another mile-and-a-quarter race, for his return after eight weeks off. In all honesty, American Pharoah could have retired the moment he crossed the finish line at Belmont and no one would have batted an eye, such is the rarity of the accomplishment. AP had two more starts after the Haskell in 2015, the Travers Stakes and then Breeders Cup Classic, where he completed the first-ever Grand Slam. After he walked out of the winner’s circle at Keeneland, American Pharoah took his place at Coolmore Ashford Stud and hasn’t been under saddle since. For Sir Barton, though, it was a different time, where the Triple Crown wasn’t a thing yet and horses ran well into their fourth and fifth years and even beyond. He would run eight more times after the Dwyer in 1919, the first of those being the Hip Hip Hooray purse.

His performance showed that he needed a race to round him back into shape. Sir Barton took the lead at the race’s start, but faded by the end of the six-furlong dash, holding on to finish second behind his stablemate Billy Kelly. Both of them gave weight to their competition, 15 to 18 pounds, and both outlasted the others, but the eight-week layoff showed in Sir Barton’s performance. Two days later, though, he would be back on the track for the Potomac Handicap, also at Havre de Grace.

Without This, The Triple Crown Isn’t

It’s not hard to think of the run for the classics as this statement about the noble pursuit of one’s best potential, a celebration of the right horse with the right jockey and trainer and owner and breeder. The intrinsic value of the attempt and the catharsis of losing or the exuberance of winning seem to be the very thing that brings us back to the Triple Crown races year after year. As the lovers of the thoroughbred, we seek the high regardless of the lows.

The Triple Crown as we know had its origins not necessarily in the noble, but in something far more practical and cynical: money. That’s right: War Cloud opened the door and Sir Barton kicked it open not for the mere doing of the thing, but because of the paychecks that came with it.

From the first Triple Crown winner Sir Barton in 1919 to the second Triple Crown winner Gallant Fox in 1930, the number of horses going for the triple increased as did the purses that they came with:

1918 Kentucky Derby – $18775
1919 Kentucky Derby – $24600
1920 Kentucky Derby – $36650
1921 Kentucky Derby – $55450
1922 Kentucky Derby – $63775
1923 Kentucky Derby – $63600 + $5000 Gold Cup
1924 Kentucky Derby – $62775 + gold cup
1925 Kentucky Derby – $62950 + gold cup
1926 Kentucky Derby – $60075 + gold cup
1927 Kentucky Derby – $61000 + gold cup
1928 Kentucky Derby – $65375 + gold cup
1929 Kentucky Derby – $63950 + gold cup
1930 Kentucky Derby – $60725 + gold cup
1918 Preakness – $17250* ($16250)
1919 Preakness – $30500
1920 Preakness – $29000
1921 Preakness – $53000
1922 Preakness – $61000
1923 Preakness – $62000
1924 Preakness – $64000
1925 Preakness – $62700
1926 Preakness – $63625
1927 Preakness – $63100
1928 Preakness – $70000
1929 Preakness – $62325
1930 Preakness – $61925
1918 Belmont – $10200
1919 Belmont – $14200
1920 Belmont – $9200
1921 Belmont – $10650
1922 Belmont – $46700
1923 Belmont – $46000
1924 Belmont – $50880
1925 Belmont – $46500
1926 Belmont – $56550
1927 Belmont – $72410
1928 Belmont – $74930
1929 Belmont – $71150
1930 Belmont – $77540

By the time Gallant Fox won the Triple Crown in 1930, each race’s purse was the equivalent of $1 million in 2016 dollars, tripling and even quadrupling the purses War Cloud (1918) ran for in some cases. So, while I do enjoy the romantic notion of the pursuit of the Triple Crown as this thing that is the ultimate accomplishment in the Sport of Kings, I know that at the heart of the whole thing, at least to start, was, quite simply, money.

(By the way, the 2016 Kentucky Derby purse will be a minimum of $2 million, the Preakness a minimum of $1.5 million, and the Belmont a minimum of $1.5 million.)

*The Preakness Stakes was run in two divisions in 1918; War Cloud won one division and Jack Hare, Jr. the other.

The Path to Immortality Started Here

Now, if you’re here, you can guess from the title of the site and the upcoming book that the first Triple Crown winner was Sir Barton. For the longest time, I never thought about it any more than that. For us, in this modern era of racing, it’s not unheard of for horses to run in all three classics, even when they don’t win the races; just the chance to run and win some money or play spoiler might be enough.

However, in the first part of the 20th century, before the Triple Crown existed as we know it, the Kentucky Derby, the Preakness Stakes, and the Belmont Stakes were just three stakes races in the spring. Sometimes the Preakness might precede the Derby and, on a couple of occasions, they were run on the same day. In fact, between 1875 and 1917, only three horses ever made the trip from Louisville to Baltimore to compete in the Derby and the Preakness.

The Maryland Jockey Club in 1918 changed that and set us on the path that we’re on today.

That year, the MJC offered a $15,000 purse for the Preakness, an extraordinary sum, but it was wartime and the powers that be wanted to keep racing going and knew that big purses were going to attract the good horses and thus bump attendance and betting. Thirty-four horses were entered and the MJC decided to split the Preakness into two divisions and then offered a $15,000 purse for each division. Only one horse made the trip from Louisville to Baltimore that year. His name was War Cloud (pictured below). He didn’t finish in the money in the Derby, but did win one of the Preakness’s divisions and then was shipped to New York.

In New York, at Belmont Park, War Cloud first started in the Withers Stakes, finishing seventh, and then in the Belmont Stakes on June 15th. For his efforts, War Cloud collected only about $16,000 in purse money, but he also drew attention to the profitability of the trek from Kentucky to Maryland to New York in such a short span of time, despite the logistical difficulties of such travel in the first part of the 20th century.

War Cloud proved that these three races could be a worthwhile endeavor; Sir Barton would seal the deal the follow year, as another increase in purse money for all three races would make what we now know as the Triple Crown an attractive path for years to come.