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How the First Triple Crown Winner Wound Up in the Army

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At Saturday's Belmont Stakes, California Chrome will attempt to become the first Triple Crown winner since Affirmed in 1978. At some point in the coverage, an announcer will likely rattle off the names of all 11 horses who have completed the Triple Crown, including familiar names like Secretariat, Citation, and Seattle Slew. Today let’s look at a champion who doesn’t get quite as much mention: Sir Barton, who in 1919 became the first horse ever to win the Derby, the Preakness, and the Belmont.

To call Sir Barton an unlikely champion is a bit of an understatement even though he had good bloodlines. The chestnut colt was sired by well-known stud Star Shoot, and his grandsire was legendary British racehorse Isinglass, who had won the English Triple Crown in 1893. Despite his speedy breeding, Sir Barton took his sweet time getting started on the track. He had tender feet – a trait he inherited from Star Shoot – that gave him a particularly nasty disposition.

It’s one thing for a horse to be disagreeable, but Sir Barton had an even bigger problem for a thoroughbred: he wasn’t very fast. Owner and breeder John E. Madden raced Sir Barton four times as a two-year-old in 1918, and he finished out of the money each time. Sir Barton had a tendency to start quickly before fading badly down the stretch, and his soft feet sometimes led to his shoes flying off mid-race.

After Sir Barton flopped in his fourth race as a two-year-old, Madden decided to get rid of what he thought was a dog of a horse. Canadian businessman and former naval commander J.K.L. Ross agreed to pay around $10,000 to take Sir Barton off of Madden’s hands. Ross turned Sir Barton over to Hall of Fame trainer H. Guy Bedwell. Bedwell cleverly addressed the soft-feet issue by inserting a strip of piano felt between Sir Barton’s hoof and shoes, and the horse started to show signs that he might eventually be a competent racer.

Sir Barton hardly enjoyed an instant turnaround, though. Ross and Bedwell entered the colt in two more races as a two-year-old. He again finished out of the money at the Hopeful Stakes at Saratoga, but in his final race of the season, the Belmont Futurity Stakes, he finally showed some stretch speed in roaring back to finish second.

Even after this promising finish to his two-year-old season, Ross and Bedwell didn’t have particularly high expectations for Sir Barton. They already had a budding superstar who was the same age, a horse named Billy Kelly. The trainer and owner decided to start Sir Barton’s three-year-old season with a run at the Kentucky Derby, but they didn’t think he would win. Instead, he was part of their strategy for helping Billy Kelly win the race. Sir Barton would act as a “rabbit”—a horse that sets a quick pace early in the race to wear out the rest of the field, particularly the favored Eternal. Once Sir Barton wore down the competition, Billy Kelly would storm past the fatigued horses to an easy victory.

Rabbit, Run

At least that was the plan. A funny thing happened at that Derby, though: Sir Barton didn’t fade down the stretch. If anything, he got stronger, and he ended up winning his first race by five lengths on a muddy track. Just four days later he proved he was no fluke by winning the Preakness Stakes by four lengths over Eternal. Ten days later he won another stakes race when he came from behind to knock off Eternal in the Withers at Belmont.

By this point, Sir Barton had won three big-name stakes races in the span of two weeks. When the Belmont Stakes rolled a few weeks later, breeders and trainers only bothered entering two other horses into the race. Probably a good call. Sir Barton again dominated while setting a new American record at the distance.

And so Sir Barton had won the first Triple Crown. There wasn’t a lot of hoopla, though. At the time, there was no such thing as the Triple Crown. The first recorded use of the term to refer to the Kentucky Derby, the Preakness, and the Belmont didn’t come until 1923. Sir Barton was just another terrific horse. He even got the nod as the 1919 Horse of the Year.

May the Best Man (o' War) Win

Sir Barton’s wins as a three-year-old were impressive, but he wasn’t the undisputed best horse in the world. Now-legendary horse Man o’ War won nine of 10 starts in 1919 as a two-year-old and would go on to win the Preakness and the Belmont in 1920. (He didn’t run in the Kentucky Derby.) On October 12, 1920, Sir Barton faced off against Man o’ War in a highly anticipated match race at Canada’s Kenilworth Park. Sir Barton’s soft feet again plagued him, and he was no match for Man o’ War, who won by seven lengths after Sir Barton lost all four of his shoes.

In retrospect, there’s no shame in losing a match race to arguably the greatest thoroughbred of all time. After this defeat, though, Sir Barton’s racing career was effectively over. He ran in three more races without a victory in 1920 before retiring to stud. He stood stud for 11 years in Virginia but never enjoyed much success as a sire. (One exception was the filly Easter Stockings, who won the 1928 Kentucky Oaks.)

Reporting for Duty

At this point, Sir Barton’s story takes another odd turn. When interest in his stud services dwindled, his owners handed him over to the U.S. Remount Service, the Army’s division in charge of breeding and supplying military horses. As part of the Remount Service’s program, the former Triple Crown winner’s stud fee dropped from hundreds or thousands of dollars to a paltry $5 or $10.

Sir Barton didn’t last long in this job, either. By the end of 1933, the Army sold Sir Barton to Dr. J.R. Hylton, who moved the 1919 Horse of the Year to his Wyoming ranch. Sir Barton died of colic on October 30, 1937, after what was surely one of the strangest lives a Triple Crown winner has ever had. Today he’s buried beneath a statue in Washington Park in Douglas, Wyoming.

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11 Classic Facts About Converse Chucks
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Converse’s Chuck Taylor sneakers have been around since the early 20th century, but they haven’t changed much—until recently. In 2015, The Chuck II—a new line of Converse that looks much the same as the original shoe but with a little more padding and arch support—hit stores. In honor of the kicks' staying power, here are 11 facts about Converse Chuck Taylor All-Stars.  

1. They were originally athletic shoes. 

The Converse All-Star debuted in 1917 as an athletic sneaker. It quickly became the number one shoe for basketball, then a relatively new sport (basketball was invented by James Naismith in 1891, but the NBA wasn't founded until 1946). By the late 1940s, most of the NBA sported Chucks. They remain the best-selling basketball shoes of all time, even though very few people wear them for basketball anymore. (Many teams switched to leather Adidas in the late ‘60s.)

2. Converse previously made rain boots.

The company started in 1908 as a rubber shoe company that produced galoshes.  

3. The All-Star design hasn’t really changed since 1917.

The updated Chuck II is Converse’s first real attempt to update its flagship product since the early 20th century. The company is understandably reticent to shake things up: All-Stars make up the majority of the company’s revenue, and like any classic design, its fans can be die-hards. In the 1990s, when the company tried to introduce All-Stars that were more comfortable and had slightly fewer design inconsistencies, hardcore aficionados rebelled. “They missed the imperfections in the rubber tape that lines the base of the shoe,” according to the Washington Post. The company went back to making a slightly imperfect shoe.

4. Chuck Taylor was a basketball player and trainer ...

Chuck Taylor in 1921. Image Credit: North Carolina State University via Wikimedia Commons // Public Domain

Taylor was a Converse salesman and former professional basketball player who traveled around the country teaching basketball clinics (and selling shoes) starting in the 1920s. His name was added onto an ankle patch on the sneaker in 1932

5. ... And though he sold a lot of Chucks, he wasn't always a great coach.

Taylor is in large part responsible for the shoe’s popularity with athletes (the company rewarded him with an unlimited expense account), but his training advice wasn’t always the best. As former University of North Carolina player Larry Brown told Spin in an oral history of the shoe:

My greatest memory of Chuck Taylor—probably ’61 or ’62—is that he told Coach [Dean] Smith that he’d make us special weighted shoes in Carolina blue. The idea was that we’d wear the weighted shoes in practice, and then during the games, we’d run faster and jump higher. Well, we tried them for one practice and everyone pulled a hamstring.

6. Converse didn’t intend for their shoes to be punk.

“We always thought of ourselves as an athletic shoe company,” John O’Neil, who oversaw Converse’s marketing from 1983 to 1997, told Spin. “We wanted to sell a wholesome shoe.” The company was still touting its shoes as basketball sneakers as late as 2012, and some of its non-Chucks sneakers still have pro endorsers.

7. The company owns a recording studio.

Finally embracing its role in the music scene, the company launched Rubber Tracks, a Brooklyn-based recording studio where bands can record for free, in 2011.

8. Not all the Ramones were fans. 

Chuck Taylors are associated with punk rockers, especially the Ramones, but not everyone in the band wore them. “Dee Dee and I switched over to the Chuck Taylors because they stopped making [the style of] U.S. Keds and Pro-Keds [that we liked],” Marky Ramone told Spin. “Joey never wore them. He needed a lot of arch support and Chuck Taylors are bad for that.”

9. Chucks were initially only high tops. 

In 1962, Converse rolled out its first oxford Chuck Taylor All-Stars. Previously, it had just been a high-top shoe. Four years later, the company would introduce the first colors other than black and white.

10. Rocky ran in them.

In 1976, All-Stars were still considered a viable athletic shoe. If you look closely at the training montage from Rocky, you’ll see the boxer is wearing Chucks. 

11. Wiz Khalifa loves them. 

The rapper named his record label Taylor Ganag Records, in part due to his appreciation for Chuck Taylors. In 2013, he launched a shoe collection with Converse featuring 12 styles. 

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