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Triple Crown Winners
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Triple Crown Dirty Dozen

Many say horse racing’s Triple Crown is the toughest feat in all of sports. When you think about it, winning three races at three different tracks at three different distances in five weeks seems to be truly impossible.

First stop, Kentucky. Save a few instances where a horse ships in from overseas, no three-year-old has carried 126 pounds or raced past 1 1/8 miles. Now they have to carry that impost and navigate the classic distance of 1 ¼ miles. Throw in the University of Louisville Marching Band playing “My Old Kentucky Home” with easily over 120,000 screaming, mostly drunk, fans singing along, and you have yourself the Kentucky Derby. Physical and mental toughness are an absolute must.

If you manage to win the Roses, it’s off to Baltimore where you get to cut back in distance to 1 3/16 miles and go from a Churchill Downs course that plays fairly even to a sometimes speed-biased Pimlico course that can be tricky at times, to say the least. There certainly isn’t as much fanfare, there are still plenty of drunks though, but with just two weeks and a 500-mile trip in between starts, there is still plenty to deal with.

Should you grab the first two jewels, the “Test of the Champion” awaits. You get three weeks between starts this time and less of a van ride but all 1 ½ miles of Big Sandy awaits. Hall of Fame trainer Allen Jerkens once made me walk around the track at Belmont, stopped me at the quarter pole and said” imagine having done all of that (everything I’ve already mentioned) and still having to do this.” To me, it seemed like the wire was a world away.

It’s astonishing that 12 have already done it, in some shape or form.

Here’s a look at the members of the most exclusive club in the Sport of Kings.

Preps? Who needs preps? A maiden going into the Run for the Roses, Sir Barton was making his first start of the year in the Kentucky Derby, a race he was entered in as a rabbit for his more championed stablemate Billy Kelly. The problem was someone forgot to tell Sir Barton and his rider Johnny Loftus that he was supposed to stop instead of draw off to a five-length win in the Derby. Another front running score followed in the Preakness before Sir Barton rated off the pace to win the Withers in between the Preakness and Belmont. Loftus employed the same rating tactics in the Belmont in route to an easy score making Sir Barton the first horse to win the three races that now make up the Triple Crown.

Trainer “Sunny” Jim Fitzsimmons became a bit of a training pioneer when he used a seven race two-year-old campaign to build a foundation for the three-year-old classics. It paid off as Earl Sande piloted Gallant Fox to a ¾ length win in the Preakness, run before the Derby that year, a two length Derby victory and a wire to wire score in the Belmont by three lengths.

OMAHA - 1935
When your sire, Gallant Fox, is Triple Crown champ expectations are high. And while he won just once in his juvenile season, Omaha came around in his sophomore year. After drawing away to win both the Derby and Preakness, Omaha fell 1 ½ lengths short in the Withers before returning to his winning ways with a gutsy Belmont Stakes victory making him and Gallant Fox the only father-son combination to win the Triple Crown and Fitzsimmons the only person to train a pair.

War Admiral led every step of the way in all three jewels of the Triple Crown in the spring of ’37 under jockey Charlie Kurtsinger and in fact won all eight starts that season. In all, he 21 of 26 career starts but he’ll best remembered for losing the most famous match race in history to the legendary Seabiscuit at Pimlico.

One of the most dangerous horses of all time, both literally and figuratively, Whirlaway had a penchant for bearing out terribly in the stretch before lugging back in just as dramatically, often giving his rider fits. For the Derby, the great Ben Jones changed the blinkers and reached out for Eddie Accaro and was rewarded for his decision with an eight-length romp in the Derby. A 5 ½ length Preakness score followed by an allowance romp set him up perfectly for the Belmont, which he won by 2 1/2 lengths.

Nearly sold as a two-year-old due to his clumsiness, jockey Johnny Longden convinced the owners to keep the colt and his advice paid off handsomely. Count Fleet won the Derby by 9 lengths, the Preakness by 8 lengths and the Belmont by an eye-popping 25 lengths in what would be the final start of his career under Longden, who rode the colt in every one of his 21 career starts.

ASSAULT – 1946
Nicknamed “The Clubfooted Comet: due to a malformed right front hoof, Assault overcame all sorts of problems both on and off the racetrack on his way to a sweep. After winning the Derby by 8 lengths, jockey Warren Mehrtens decided to make a premature move in the Preakness after getting bothered at the start before holding on for a neck victory. More trouble waited at Belmont as he stumbled at the start and was last in the early going before exploding past the field to win by 3 lengths.

Racing’s first millionaire had little trouble sweeping the Triple Crown with Accaro aboard. At one point in his career, Citation rattled off 16 straight scores, a feat duplicated at the top level of the sport most famously in 1995 and 1996 by the great Cigar.

Horse of the Year at two, Secretariat turned the Triple Crown events in to one of the most brilliant showcases in all of sports. He broke the track record, going every quarter of a mile faster, in the Derby with a 2 ½ length score before a timer malfunction deprived him of the course record at Pimlico in the Preakness which he won by the same 2 ½ lengths. Then, in the most historic race the Sport of Kings has ever seen, Secretariat turned in arguably the most impressive performance in the history of sports with a world record setting Belmont score that saw him cross the wire 31 lengths ahead of his closest rival, turning the “Test of the Champion” into a one-horse show under Ron Turcotte.

The only horse to remain undefeated through the Triple Crown, Seattle Slew was purchased for the bargain basement price of $17,500 as a two-year-old before winning all three events in impressive, wire-to-wire fashion under Jean Cruget. He was the last living Triple Crown winner until his death on May 7th, 2002 which was the 25th anniversary of his Derby triumph.

Affirmed was part of the sports’ greatest rivalry, having defeated the equally impressive Alydar in all three events. Under Steve “The Kid” Cauthen, the youngest rider to win the Triple Crown at the age of 17, Affirmed won the Derby by 1 ½ lengths and the Preakness by a neck before coming to Belmont with a chance to complete the sweep. In one of the most memorable Belmont Stakes moments, Affirmed and Alydar were never more than a length apart for the entire 1 ½ miles with Affirmed battling back along the inside to get his head back in front of a stubborn Alydar to complete the sweep.
“The 37-year wait is over! American Pharoah is finally the one!!!!” That was the call of Larry Collmus for Belmont Stakes 147 when over 90,000 fans watched history being made on a sun-splashed day at Belmont. He was named Two-Year-Old Champion despite missing the Breeders’ Cup Juvenile due to a foot injury, one that forced him to wear a slightly-altered shoe that had a small aluminum pad attached through his historic run for Hall of Famers Bob Baffert and Victor Espinoza.

Anthony “the Big A” Stabile can be heard regularly on the Horse Racing Radio Network from 3-6:00 p.m. ET on Wednesday and 3-7:00 p.m. ET on Thursday and Friday. Tune in on Sirius 219, XM 201 or streaming live at He also is a contributor on NYRA-TV as a guest on Talking Horses. Follow him on Twitter at @TheBigAStabile

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Mike Dempsey Mike covers the New York racing circuit (Aqueduct, Belmont Park, and Saratoga) year-round as well as covering the biggest events including the Kentucky Derby, Preakness Stakes, Belmont Stakes and the Breeders’ Cup.
A professional handicapper and horseplayers for more than three decades, no handicapper in the industry works harder and been more successful in bringing horseplayers analysis that produces profits at the track!

Mike has owned racehorses and knows the racetrack from the backstretch to the finish line.

Mike is in his second decade of producing great results for the readers of Vegas Insider. Among his scores in the Kentucky Derby include winning with his top pick Animal Kingdom who paid $43.80 in 2011 and Super Saver at $18.00 in 2010.

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Jerry Sessa Jerry "Shots" Sessa has been involved in horse racing for over 30 years. He now brings his meticulous handicapping style to When Jerry posts picks you are getting his best bets...when you win, he wins.
Jerry opened the 2016 Triple Crown season by hitting his Derby Day best bet, Nyquist. He also nailed the Derby exacta for a $30.60 payout. On 4/16/16 at Keeneland, Jerry hit an $819 exacta that led to a $38k Trifecta & a $300k Super.

In the 2015 Belmont Stakes Jerry dominated races 8-11 by hitting a $4,400 Pick 4, 3 Daily Doubles, 2 Pick 3's and calling American Pharoah as the first Triple Crown winner in 36 years.

Jerry is always looking to repeat his 2012 Triple Crown success, when he selected the winning horses for The Preakness and The Belmont Stakes.

Jerry looks forward to working with everyone and making money for anyone who invests in his picks on a daily basis.

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