TRIPLE CROWN HEARTBREAK- The 20 Horses To Come Closest Since The Last Triple Crown Winner

As much as I wanted to believe that Orb would be the horse to finally break the Triple Crown drought, which extends longer than the duration of my life, his 4th place finish in the Preakness just once again demonstrated what an incredibly difficult feat that is to accomplish. Orb was by far the most talented runner in the field, but variables like an inside post, a bad trip, and slow early fractions on the lead made it difficult for him to run his race and make up any ground on the leader, another horse that I really like in Oxbow. It got me thinking, in what is now 35 years since Affirmed won all three races, which horses were closest to doing the impossible and winning the Triple Crown?

I’ve broken down these horses into four basic groups: those that won the Derby and Preakness and then lost the Belmont, horses that won the Preakness and Belmont after not winning the Derby, horses that won the Derby, then lost the Preakness but came back to win the Belmont, and finally, horses that won one of the three races and finished second in the other two. Of course the first group is the one that are the most memorable and climactic, but there are many other horses that could argue that they were just as close, and in many cases, closer.

In light of the probable event that Orb and Oxbow meet again in the Belmont with a chance to add one of their names to this list, it seems a worthy exercise. In what may seem a bit contradictory to the spirit of the win, I’ve decided to post video of each horse’s most heartbreaking LOSING effort in the Triple Crown series, as that is what this list is supposed to address…who was the closest to breaking the drought, and how did they fall short of racing immortality? I’ve tried to make the breakdown as logical as possible, with quantity as well as quality of defeat(s) being taken into account.

#20: VICTORY GALLOP, 1998 (2nd Derby, 2nd Preakness, 1st Belmont)

As soon as I saw his hard closing 2nd place finish coming all the way from last in the Kentucky Derby (below), I knew I had my Belmont pick. A change of tactics in the Preakness found him more forwardly placed, where he was no match for the Derby winner, but it sure set up a great one three weeks later.

#19: EASY GOER, 1989 (2nd Derby, 2nd Preakness, 1st Belmont)

He deserves to be much higher on this list, but since he only was able to capture one of the Triple Crown jewels, I am forced to place him here by default. However, you could argue his loss in the Preakness to Sunday Silence, one of the very greatest horse races ever run (below), was as close to a win as you can get. He turned the tables big time three weeks later and got his revenge, winning the Belmont going away.

#18: HANSEL, 1991 (10th Derby, 1st Preakness, 1st Belmont)

Who knows what happened to him in the Derby (below). He ran close to the pace but it wasn’t a terribly torrid one, he simply tired after the mile mark. Perhaps he simply needed another conditioning race, as he came back to dominate the Preakness by seven lengths, and held off the Derby winner by a length in the Belmont.

#17: WAR EMBLEM, 2002 (1st Derby, 1st Preakness, 8th Belmont)

Overlooked with a field high 120 Beyer, which sounds crazy by today’s standards, he took advantage of a lack of speed in the Derby and took his competitors wire to wire, the last horse to win that race in that fashion. In the Belmont, the long campaign caught up with him, as he broke poorly and was forced too fast run early, fading to 8th in the stretch as 70-1 shot Sarava ruined his Triple Crown attempt in the biggest upset in Belmont history (below).

#16: SWALE, 1984 (1st Derby, 7th Preakness, 1st Belmont)

After winning the Kentucky Derby, Swale shipped to Pimlico and posted a blowout work the Monday before the Preakness. He chased a torrid opening half mile in :45.1 and that work may have taken its toll, as he faded to 7th (below). Swale would come back in top form to win the Belmont, but tragically collapsed and died eight days later.

#15: TABASCO CAT, 1994 (6th Derby, 1st Preakness, 1st Belmont)

This was the first Derby I ever watched live, and the controlled, wire to wire victory by Go For Gin over the sloppy track didn’t bode well for Tabasco Cat’s closing style (below). He would take the final two races of the Triple Crown, an impressive feat indeed considering the overall strength of that class.

#14: ALYSHEBA, 1987 (1st Derby, 1st Preakness, 4th Belmont)

After winning the Derby in a gutsy performance following a stumble and near disaster on the heels of rival Bet Twice, that one turned the tables big time in New York and crushed Alysheba’s Triple Crown bid, winning by 14 lengths (below).

#13: THUNDER GULCH, 1995 (1st Derby, 3rd Preakness, 1st Belmont)

This was the first Triple Crown season that I was fully involved in, and also my first Derby winning pick at a healthy 25-1. He didn’t miss by much in the Preakness, as he was beaten by the winner Timber Country by about a half a length in a thrilling stretch duel (below), and then came back to win the Belmont in equally exciting fashion. I’ll always remember the blinkers.

#12: BIG BROWN, 2008 (1st Derby, 1st Preakness, DNF Belmont)

I’m breaking the rules a bit to have him ranked this highly considering he was eased in the Belmont and didn’t finish the race, but words can’t really express how shocking that race was. The fear to race Big Brown was so extreme that he faced virtually no rivals in the Preakness or Belmont, and the Triple Crown victory was all but assured. But that’s why they run the races; his connections certainly were’t the most popular, so maybe the racing gods had a say. I still can’t explain what happened here or how the hell Da’Tara was able to win this race (below). This was the race that made me realize that I may never see a Triple Crown winner as long as I live.

#11: PLEASANT COLONY, 1981 (1st Derby, 1st Preakness, 3rd Belmont)

After narrow victories in the Derby and Preakness, Pleasant Colony just didn’t have quite enough in the Belmont (below). He was a factor throughout but his closing move was too little to late, and the second of many more failed Belmont attempts since Affirmed.

#10: FUNNY CIDE, 2003 (1st Derby, 1st Preakness, 3rd Belmont)

Over the years I’ve been picking Derby winners, if you’d asked me my single most confident pick, I would undoubtedly reply “Empire Maker in 2003.” Funny Cide, the gutsy gelding, proved me wrong that day, but after skipping the Preakness to freshen up, my Derby pick turned the tables in the Belmont and ended another Triple Crown dream (below).

#9: CHARISMATIC, 1999 (1st Derby, 1st Preakness, 3rd Belmont)

After being completely overlooked in the Derby at 31-1, he went on to defeat the second place finisher there again in the Preakness. He battled gamely in the Belmont and actually had the lead at the top of the stretch, but the long spring campaign took its toll–Charismatic had broken his leg in two places during the effort (below). Jockey Chris Antley memorably jumped off the horse, who still managed to finish third, held up his broken leg, and ultimately saved his life. Had he not sustained that injury, who knows?

#8: RISEN STAR, 1988 (3rd Derby, 1st Preakness, 1st Belmont)

Wire to wire Derby wins are a rare thing to behold, but in 1988 Winning Colors took the field from start to finish as jockeys gambled she would fade late, and lost. But Risen Star was closing hardest of all, never getting the pace to run into that he would have ideally benefited from, and losing a lot of ground by running wide around the final turn (below). He would come back to win the Preakness, and then crush his competition by nearly 15 lengths in the Belmont. With a less speed favoring Derby scenario, he may have been the one to end the drought, but alas…

#7: POINT GIVEN, 2001 (5th Derby, 1st Preakness, 1st Belmont)

I’m breaking the rules again here, and even though he lost the Derby to perhaps my favorite horse of all time in Monarchos, I’d be doing a disservice to the sport to not put the wicked pace set by Songandaprayer into perspective, as the frontrunner set the single fastest splits for the 1/2 and 3/4 in Derby history (:44.86, 1:09.2). Point Given was a bit too close to that hot pace, and even though I still believe that no one was beating Monarchos that day, he certainly still should have been second rather than fifth under normal racing conditions (below). He would go on to win the Preakness and Belmont with ease, and added the Travers for good measure in route to Horse of the Year honors in 2001. (Also one of Tom Durkin’s top 3 race calls ever).

#6: SPECTACULAR BID, 1979 (1st Derby, 1st Derby, 3rd Belmont)

In perhaps the greatest upset over all of these 35 years, as well as one of the very worst rides in the history of the sport, Spectacular Bid chased hot opening fractions and moved way too soon to take control of the race before the halfway point. Some believe that he was trying to duplicate Secretariat’s Belmont, but he didn’t have enough left in the tank after making such an early move. He faded to third after leading the field turning for home, and the Triple Crown drought began (below).

#5: SUNDAY SILENCE, 1989 (1st Derby, 1st Derby, 2nd Belmont)

The legend of his rivalry with Easy Goer often leads many to bring him up as the primary horse over this time period that should have won a Triple Crown. The argument goes that in most other years, without a horse of the caliber of Easy Goer to contend with he would have easily captured all three races. It is true that 1989 is one of only two years where I have included two horses on this list, but the fact remains that he was pretty easily beaten by his arch rival in the Belmont (below), whereas the horses I have ranked ahead of them lost much more narrowly. Additionally, again, with credit to Easy Goer, he didn’t dominate the Preakness as well as some of these did as well.

#4: AFLEET ALEX, 2005 (3rd Derby, 1st Preakness, 1st Belmont)

If I am willing to forgive Point Given for being too close to a hot pace in 2001, I’d have to do the same for Afleet Alex, who did the same with a rough trip as well as a lung infection and still managed to hit the board in one of the most bizarre Kentucky Derbies ever. I was in attendance as the rabbit Spanish Chestnut took the field through the second quickest opening 3/4 in history, and I’ll never forget the utter silence of the crowd as 50-1 shot Giacomo crossed the wire first by less than a length over the next two finishers (below). The remarkably athletic Afleet Alex would come back to win the Preakness after nearly falling during a collision coming around the final turn in one of my favorite races ever, and then decimated his opponents in the Belmont. If there is one horse that probably “should” have won the Triple Crown, it would have to be him.

#3: SILVER CHARM, 1997 (1st Derby, 1st Preakness, 2nd Belmont)

After winning the 1997 Kentucky Derby by a narrow head, Silver Charm came back to win the Preakness in a three horse photo finish in one of the most exciting finishes in that race’s history. He took the lead in the top of the stretch in the Belmont, and it looked to be setting up as another rematch with rival Free House, who had finished 3rd and 2nd in the prior two races. Alas, the added distance of the Belmont proved just a bit too much as it often does, especially after a wide early trip, and Touch Gold (who happened to be my pick to win the race) got up just in time to win by three parts of a length, and ruin the first Triple Crown attempt in eight years (bel0w).

#2: SMARTY JONES, 2004 (1st Derby, 1st Preakness, 2nd Belmont)

Smarty Jones was the last undefeated horse since Seattle Slew to win the Kentucky Derby when he did so in 2004, and after winning the Preakness decisively by nearly a dozen lengths, he was understandably a heavy favorite to finally break the Triple Crown drought in the Belmont, going off at odds of 1-5. After opening up on the field coming for home, he appeared poised to do just that. I still watch this race (below) imploring Smarty to hold on, yet the wicked Birdstone always gets there to pull off the upset by a length in arguably the most shocking and disappointing Belmont of all.

#1: REAL QUIET, 1998 (1st Derby, 1st Preakness, 2nd Belmont)

Real Quiet was my Derby pick in 1998, but as mentioned above, as soon as I saw the way Victory Gallop closed into him when second in that race, I knew who I was picking to win the Belmont. In a famously debated act of riding, Kent Desormeaux probably moved too soon with the late closing colt, opening the door for an even later closing rival. Still, it is amazing to re-watch this race (below) and wonder how on earth Victory Gallop was able to make up so many lengths in deep stretch. The resulting photo finish was literally too close to call initially, and by definition Real Quiet was therefore horse that came the closest to actually winning the Triple Crown based on margin of defeat. I went ahead and posted both the ABC telecast with Dave Johnson on the call as well as the track call from Tom Durkin- arguably his greatest ever.

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