As the oldest of the three Triple Crown races, the Belmont Stakes Presented by NYRA Bets has seen its fair share of upsets, and the majority of those have come in roughly the last third of the race’s 154-year history. During the post-World War II era, 20 horses have come into the Belmont Stakes with wins in the Kentucky Derby and Preakness Stakes, only to have their bids for immortality denied (this includes I’ll Have Another in 2012, who was scratched the day before the Belmont with an injury). Also, the eight highest-priced Belmont Stakes winners have all come since 1961. Five times, those two statistical nuggets occurred in the same race.

In advance of Belmont Stakes 155 on June 10, which is shaping up to be a wide-open affair capable of producing its own unpredictable result, let’s take a look back at 10 of the race’s most memorable upsets.

1958: Cavan defeats an injured Tim Tam

Click image to purchase shirt.

Tim Tam entered the 1958 Belmont on a six-race winning streak and was expected to carry the devil’s red and blue silks of storied Calumet Farm to a third Triple Crown, joining Whirlaway (1941) and Citation (1948). A homebred son of the legendary Tom Fool, Tim Tam had made valiant charges from off the pace to take two of Florida’s big prep races, the Fountain of Youth and the Florida Derby, plus an allowance at Keeneland prior to winning the Derby Trial at Churchill Downs and – four days later – taking the Kentucky Derby by a half-length. He then won the Preakness by a length and a half, and was sent off as a prohibitive 0.15-1 favorite in the 90^th Belmont.

Irish-bred Cavan, coming off of win in the Peter Pan Stakes, made a move for the lead heading into the far turn at Belmont and was joined by Tim Tam, but the 4.90-1 shot kept his advantage entering the homestretch and then drew away to win by six lengths. Tim Tam, who finished a clear and hard-trying second, was found after the race to have fractured a sesamoid bone in his ankle, which made his performance even more admirable. Fortunately, while his racing career was finished, Tim Tam went on to become a successful sire at Calumet for many years, dying in 1982 at 27. He was inducted into the Racing Hall of Fame in 1985 and remains the lowest-priced odds-on favorite to lose the Belmont Stakes.

1961: Sherluck shocks Carry Back

The next Belmont upset on our list tells a similar story. Carry Back was a working-class hero of a horse, rising from modest beginnings to race an incredible 21 times as a 2-year-old and then winning four of seven starts in 1961 prior to the Kentucky Derby for co-owner, breeder, and trainer Jack Price (see Keeler Johnson’s ABR feature on Carry Back for more on his backstory). He gave fans a thrill in most of his victories, coming from off the pace and weaving through traffic to get up in time, and that form held true in his first two Triple Crown races as he closed from 18 lengths back to win the Kentucky Derby by three-quarters of a length, and then charged from 15 lengths behind to win the Preakness by the same margin. The Florida-bred son of obscure sire Saggy was the 0.45-1 favorite for the Belmont, facing eight opponents, including 65.05-1 longshot Sherluck, the Blue Grass Stakes winner who had finished fifth in both the Derby and Preakness.

With former President Dwight Eisenhower and former First Lady Mamie Eisenhiower in attendance at Belmont Park, Carry Back lived up to his name and running style by settling well off of the pace set by Globemaster, with Sherluck pressing in second. The Derby and Preakness winner never made his patented rally, and Sherluck and Braulio Baeza forged ahead of Globemaster in late stretch to win by 2 ¾ lengths and become (at that time) the highest-priced Belmont Stakes winner in history.

Carry Back came out of the Belmont with an ankle injury and was given a much-needed break by Price. He returned in August 1961 with a win and continued to race until fall 1963, winning important races such as the Met Mile and Whitney Handicap. A truly durable champion, he retired with 21 wins, 11 seconds and 11 thirds in 61 starts and lived until age 25, passing away in 1983. Carry Back was inducted into the Racing Hall of Fame in 1975.

1971: Pass Catcher ends Canonero II’s fabulous run

Canonero trains at Churchill Downs. (BloodHorse photo)

Canonero II was the story in horse racing in spring 1971. Bred in Kentucky but based in Venezuela, he had started twice in the U.S. as a 2-year-old without success and was brought back to the states for the Kentucky Derby after winning seven of 10 starts south of the border. Regarded as an afterthought in the Derby, and included in the six-horse mutual field wager at 8.70-1 odds, Canonero II shocked observers by romping by 3 ¾ lengths. He backed that up with a 1 ½-length, track-record score in the Preakness two weeks later, and by then the horse’s Venezuelan connections had charmed the press and public with their confidence and joie de vivre. The excitement only intensified during the three weeks leading up to the Belmont, even as reports surfaced that Canonero II’s training had been paused due to a skin rash and a minor foot issue.

Before a then-record Belmont Stakes crowd of 82,694, Canonero II took the early lead and held it through the backstretch but began to receive pressure entering the far turn, and Pass Catcher rallied from third to move past him and spurt clear at the top of the stretch. That colt, a 34.50-1 outsider, had finished a close second in a stakes race at Garden State Park in New Jersey only five days prior and was wheeled right back in the Belmont by trainer Ed Yowell. With Walter Blum up, Pass Catcher held off a late challenge from deep closer Jim French to win by three-quarters of a length at odds of 34.50-1, while 7-10 favorite Canonero II faded to fourth.

The cover page of Sports Illustrated read “Canonero Should Not Have Run,” and the race recap quoted a veterinarian who said following the Belmont that the colt’s interruption in training indeed took its toll on his ability to conquer the “Test of the Champion.” Canonero II was bought by Robert Kleberg’s King Ranch for $1.5 million after the Belmont and kept in the U.S., but he never regained his Derby and Preakness form, winning only once – a five-length victory over 1972 Derby and Belmont winner Riva Ridge – in eight more starts. Read more about him in Bob Ehalt’s ABR feature.

1979: Coastal wins as “the Bid” is denied

Click image to purchase shirt.

The 1979 Belmont qualifies as an upset despite winner Coastal carrying respectable 4.40-1 odds. Why? Because of the quality of the third-place finisher: one of the sport’s all-time best. Spectacular Bid had already been voted champion 2-year-old male of 1978 and won his first five starts at 3 by open lengths leading up to the Kentucky Derby. On the first Saturday in May, he dominated the field at Churchill under 19-year-old rider Ron Franklin, winning by 2 ¾ lengths. He followed that with a 5 ½-length romp in the Preakness, and by that point seasoned reporters and railbirds were at the very least willing to concede that trainer Bud Delp’s touting of Spectacular Bid as “the greatest horse to ever look through a bridle” wasn’t completely far-fetched. 

Sent off as a 3-10 favorite in the 111^th Belmont, Spectacular Bid sat in second through the first turn, and midway through the backstretch Franklin urged him to the lead. The pace was already swift, and Franklin did not give Spectacular Bid a breather once the horse was in front, a decision that was criticized by Delp’s son – a fellow teenager – and some horse racing scribes afterward. Despite that, the colt appeared to be in command of the race and on his way to giving the public a third consecutive Triple Crown until he passed the quarter pole, when he began to shorten stride.

Coastal, a lightly raced but well-regarded colt who had won the Peter Pan Stakes and was nominated to the Belmont, had been stalking well back in fourth, but at the top of the stretch he rallied on the rail and then moved past Spectacular Bid nearing the sixteenth pole. Spectacular Bid, spent but still trying hard, was nipped by neck for second at the finish by Preakness runner-up Golden Act, as Coastal finished with a 3 ¼-length victory. The day after the race, Delp told the press that Spectacular Bid had stepped on a safety pin the morning of the Belmont but that the mishap did not appear to have hurt him at all. Whether that or Franklin’s ride had anything do to with his Belmont effort are topics still debated today by those who bet on the Bid to make history.

Ridden by Bill Shoemaker thereafter, Spectacular Bid won three of his final four starts in 1979 (losing to 1978 Triple Crown winner Affirmed by three-quarters of a length in the Jockey Club Gold Cup). He then went undefeated in nine starts in 1980, finishing up one of the most accomplished seasons in horse racing history with a walkover in the Woodward Stakes. Spectacular Bid retired as the all-time leading money winner in North America with purse earnings of nearly $2.8 million and with a record of 30 starts, 26 wins, 2 seconds, and 1 very momentous third. Read more about the 1982 Hall of Fame inductee in Bob Ehalt’s ABR profile.

1980: Temperence Hill upstages Genuine Risk

Buildup to the 112^th Belmont Stakes focused on Genuine Risk’s bid to become the first filly to win the race since 1905. The Leroy Jolley trainee had already scored an upset victory in the Kentucky Derby and then finished second to Codex – trained by a young upstart named D. Wayne Lukas – in the Preakness. Temperence Hill, meanwhile, shipped in under the radar, having missed the Kentucky Derby and Preakness. The colt, owned by John Ed Anthony’s Loblolly Stable and trained by Joseph Cantey, had won the Arkansas Derby (then a modest achievement) but was 0-for-6 away from Oaklawn Park and was not nominated to the Kentucky Derby.

Despite three straight losses in New York and Pennsylvania, Anthony paid a late fee to nominate his colt to the Belmont, and Temperence Hill was ignored by the betting public at 53.40-1 odds. Racing on a muddy track, Temperence Hill rated in sixth through the backstretch and methodically made his way up into contention as the field hit the far turn. Genuine Risk was right there as well, and that pair engaged leader Rockhill Native in early stretch for a battle of wills that saw Temperence Hill edge away late by two lengths over a game Genuine Risk (Codex finished seventh).

Temperence Hill proved to be no one-race wonder, winning the Travers Stakes, the Jockey Club Gold Cup, and the Super Derby later in 1980 to earn the Eclipse Award as champion 3-year-old male. Genuine Risk returned to racing against her own sex and closed out her career with three more wins in five starts en route to a spot in the Hall of Fame in 1986. Read more about the champion filly in Keeler Johnson's ABR profile.

1999: Lemon Drop Kid upsets, Charismatic hurt

A Triple Crown was on the line for the third consecutive year in the 131^st Belmont Stakes, following near-misses by Silver Charm in 1997 and Real Quiet in 1998. Charismatic, owned by Robert and Beverly Lewis and trained by D. Wayne Lukas, had risen out of the claiming ranks in early 1999 to score a 31.30-1 upset in the Kentucky Derby and then win the Preakness as well. By the time the Belmont rolled around, he was no longer overlooked and went off as the 8-5 favorite, with Derby and Preakness runner-up Menifee the 2.60-1 second choice and future Hall of Fame filly Silverbulletday also well-backed at 5.10-1.

Lemon Drop Kid, on the other hand, was a 29.75-1 longshot based on his mediocre 3-year-old campaign. He had won the Grade 1 Futurity Stakes at Belmont Park as a 2-year-old for owner Jeanne Vance and trainer Scotty Schulhofer but was only 1-for-4 in 1999 going into the Belmont, that victory coming in an allowance race at Keeneland. However, he did finish a sneaky-good third in his final Belmont prep, the Peter Pan Stakes, when he was in tight quarters late and racing on a muddy track. Schulhofer kept him at Belmont Park and wheeled him right back in the 1 ½-mile classic two weeks later.

Jockey Chris Antley sent Charismatic to sit just off of Silverbulletday’s pace through the backstretch, and Charismatic moved up to engage her on the far turn as Lemon Drop Kid rallied from midpack under Jose Santos. Lemon Drop Kid’s momentum carried him to the lead in midstretch and Vision and Verse, a 54.75-1 shot, also moved past Charismatic along the inside as the dual classic winner began to struggle. Lemon Drop Kid and Vision and Verse battled to the finish line, with Lemon Drop Kid winning by a head and triggering a $1,537 exacta.

As it turned out, Charismatic suffered a condlyar fracture in midstretch, and was pulled up at the finish by Antley in a move that was credited with saving his life. As with Tim Tam 41 years earlier, an unfortunate injury in the Belmont led to a happy ending, as Charismatic was retired and lived for 18 more years, passing away in 2017 at Old Friends retirement farm in Georgetown, Ky. (read more about him in Bob Ehalt’s ABR profile). Meanwhile, Lemon Drop Kid went on to win the Travers later that summer and have an even better year in 2000, when he won the Whitney Handicap, Woodward Stakes, Brooklyn Handicap, and Suburban Handicap. He was voted champion older male that year and later became a successful sire.

2002: Sarava lights up the tote board, War Emblem stumbles

Click image to purchase shirt.

The 134^th Belmont Stakes ended with a 70.25-1 winner and yet another Triple Crown bid dashed, this time due to a very untimely stumble out of the starting gate. War Emblem had romped in the Kentucky Derby and won by three-quarters of a length in the Preakness by flashing elite speed from the outset and showing enough stamina to hang on late. He was 2-for-2 for trainer Bob Baffert after Prince Ahmed bin Salman of the Thoroughbred Corporation transferred the colt to Baffert’s barn, and there was little suspense to Baffert’s and jockey Victor Espinoza’s strategy for the Belmont: “Get in the gate, break, and go,” the trainer told Sports Illustrated.

The opposite happened. War Emblem nearly went to his knees immediately after the gate opened, and Espinoza had to rush the 1.25-1 favorite up into contention while being bottled up on the inside as the field made its way through the backstretch. War Emblem engaged pacesetter Medaglia d’Oro in a bid for the lead entering the far turn but could not take over, and by the five-sixteenths pole he was finished.

For most of the spring, Sarava had been third fiddle in trainer Ken McPeek’s barn behind Florida Derby and Blue Grass Stakes winner (and Kentucky Derby post-time favorite) Harlan’s Holiday and the injured Louisiana Derby winner Repent. McPeek decided to enter Sarava after he won the Sir Barton Stakes at Pimlico on the Preakness undercard, and under Edgar Prado, the longshot moved up between horses entering the stretch and then dueled with Medaglia d’Oro to the finish, prevailing by a half-length. His $142.50 return for a $2 bet set a Belmont Stakes record that still stands. Sarava would never win again, while War Emblem tallied one more victory in his three remaining starts – a wire-to-wire score in the Haskell Invitational. Sarava now resides at Old Friends, and War Emblem died there in 2020.

2004: Birdstone silences a record crowd

Birdstone breaks hearts in the Belmont. (Adam Coglianese/NYRA)

The 2004 Belmont Stakes may have not set the parimutuel record for “biggest upset” – see the previous entry – but it holds top status among modern-day horse racing fans as the most heart-wrenching finish, without question. That June, anticipation for the Belmont Stakes was at a level not seen since the sport’s heyday of the 1970s – not even the Triple Crown bids of fan favorites Silver Charm and Real Quiet in the 1990s or the rivalry between Sunday Silence and Easy Goer in 1989 could compete. And it was all because of Smarty Jones. The Pennsylvania-bred had captured the attention of a nationwide sports audience after going undefeated through eight starts, the most recent wins coming by 2 ¾ lengths in the Kentucky Derby and an amazing 11 ½ lengths in the Preakness. He was the proverbial “little guy’s” horse with Keystone state connections, owned by elderly Roy and Pat Chapman, trained by John Servis, and ridden by journeyman Stewart Elliott. But his talent was regal, and he towered above a Belmont field that included Birdstone, a well-bred colt owned by Saratoga icon Marylou Whitney and trained by Nick Zito who had nevertheless disappointed on the track, coming into the Belmont off of an eighth-place Derby finish, 15 ¼ lengths behind Smarty Jones.

As such, Smarty Jones was sent off as the 0.35-1 favorite in the nine-horse Belmont field, while Birdstone was 36-1. Before a still-record crowd of 120,139 eager to witness history, Smarty Jones broke well from the outside post but was kept just off the early lead by Elliott until the field hit the backstretch. Much as with Ron Franklin’s ride 25 years earlier on Spectacular Bid, horseplayers and fans still debate about whether Elliott moved too soon on Smarty Jones. He took over after the half-mile marker and continued on well through the long backstretch despite being pressured, and midway through the far turn Elliott let his colt run freely and Smarty opened up on the field.

As Smarty Jones entered the homestretch, only one horse had a chance to catch him – Birdstone, who had grinded his way into second under Edgar Prado. For a few fleeting moments, it appeared that Smarty Jones, although tiring, just might have enough left to hold off his challenger and become the first Triple Crown winner since 1978. But in the final strides, Smarty gave up the lead and a multitude of desperate cheers suddenly stopped. Birdstone prevailed by a length, and such was the disappointment that Zito, Prado, and Whitney tempered their post-race remarks with offers of consolation for the legion of Smarty fans. He never raced again, but 19 years later, Smarty Jones remains arguably the most popular North American racehorse of the 21^st century, and the pivotal player in a Belmont Stakes that no one who watched it will ever forget. Read about him in Tom Pedulla’s ABR profile.

2008: Da’ Tara wires ’em, Big Brown fizzles

Big Brown before the Belmont no-show. (Adam Coglianese/NYRA)

Although not reaching the level of Smarty Jones, 2008 Triple Crown hopeful Big Brown had generated some positive fan support entering the Belmont with his unbeaten 5-0 record and open-length wins in the Kentucky Derby and Preakness Stakes. Owned by a group headed by Mike Iavarone’s IEAH Stables and trained by the loquacious and controversial Rick Dutrow, Big Brown had clearly established himself as the best of his age group and was a heavy 3-10 favorite in the Belmont – the lowest odds for a post-time favorite since Spectacular Bid in 1979. Some concerns lingered, however. For one, his pedigree was very suspect for the taxing 1 ½-mile “Test of the Champion.” Second, Big Brown had developed a quarter-crack after the Preakness that had interrupted his training. And lastly, Dutrow told reporters that in mid-May, the colt did not receive a monthly injection of what was at that time a legal steroid, raising questions about whether his accomplishments earlier in the spring were enhanced by the drug.

Whatever the cause, Big Brown was a near-total non-factor in the Belmont, breaking erratically from the rail post and fighting jockey Kent Desormeaux’s attempts to control him through the first turn and into the backstretch. Meanwhile, unheralded Da’ Tara, the longest shot in the nine-horse Belmont field at 38.70-1, went right to the lead under Alan Garcia and was never challenged. By the time Da’ Tara rolled into the stretch en route to a 5 ¼-length win over Denis of Cork, Desormeaux had pulled Big Brown up and directed him off of the track.

Da’ Tara gave Nick Zito his second Belmont win four years after Birdstone’s upset over Smarty Jones. The emotional tenor in the Belmont grandstand was decidedly different this time, however, with annoyance and even schadenfreude replacing sadness. Big Brown did gain a measure of redemption by winning the final two starts of his career, including the Haskell Invitational, but trainer Dutrow was suspended in 2013 by the New York State Gaming Commission for 10 years due to numerous medication violations (he has returned to training this spring). 

2014: Tonalist proves best, ‘Chromies’ deflated

Tonalist wins a thriller. (Eclipse Sportswire)

Ten years after Birdstone spoiled Smarty Jones’ bid for Triple Crown glory, another spunky colt from modest origins came along to captivate fans nationwide. California Chrome was a California-bred by the obscure sire Lucky Pulpit, and his owners Perry Martin and Steve Coburn bought the his dam Love the Chase for only $8,000. His trainer, septuagenarian Art Sherman, was highly respected on the Golden State racing circuit but hardly a household name. California Chrome first rose to prominence with wins in Santa Anita Park’s Derby preps with jockey Victor Espinoza aboard, and during May, when he scored authoritative wins in the Kentucky Derby and Preakness, a social-media fueled fanbase known as “Chromies” emerged to boost his popularity.

Racing followers rode a whirlwind of excitement into the 146^th Belmont, where California Chrome was sent off as the 0.85-1 favorite against a quality field. Among the challengers was 9.20-1 Tonalist, a colt owned by Robert Evans and trained by Christophe Clement who was improving at just the right time and had won the Peter Pan Stakes on Belmont’s main track four weeks earlier. In the Belmont Stakes, California Chrome stumbled out of the gate but recovered quickly to stalk the pace in fourth, one spot behind Tonalist. Both colts had good trips chasing 28-1 longshot pacesetter Commissioner through Belmont’s long backstretch, and they remained in contention through the far turn, setting up a thrilling finale.

The cheers for California Chrome from 102,199 fans in attendance (third-largest in history) were deafening, but he did not accelerate in the stretch the way he had in his six consecutive wins entering the Belmont, finishing a close fourth. Tonalist, on the other hand, had just enough stamina to overtake a game Commissioner and win by a head under Joel Rosario. Tonalist's victory was somewhat overshadowed by Steve Coburn’s post-race sour grapes gripe to NBC’s Kenny Rice about the taxing nature of the Triple Crown’s five week schedule, but as it turned out, California Chrome had simply failed to maintain his classic-winning form for a third straight race – joining a talented and accomplished club in that regard. He certainly bounced back, going on to win races such as the Dubai World Cup and Pacific Classic over the next 2 ½ years to burnish credentials that made him a 2023 inductee into the Racing Hall of Fame (read about him in Tom Pedulla’s ABR profile). Tonalist as well racked up more big wins, taking the prestigious Jockey Club Gold Cup in both 2014 and 2015.