The Six Greatest Kentucky Derby Performances of All Time

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TwinSpires Staff

April 14th, 2015


Having studied virtually all of the three-year-old crops since 1896, I've been asked before to name which horse or horses I think ran the best performance ever in the Kentucky Derby.

I thought it would make an interesting topic to do a top 10 list on the subject, however, that idea proved to be a frustrating challenge because I felt that six performances had to make the list, but trying to fill out the final four spots from the remaining 100-odd races was an impossible task. Essentially, I was trying to split hairs to determine those final four spots.

So, instead of a top ten list that was sure to feature some controversy and second-guessing, here are the six performances that I believe stood out as absolute must inclusions on my aborted Top 10 list. What's more, I felt so uneasy trying to rate these six performances that I simply will present them in order of oldest to most recent.

1914 Old Rosebud

Coming into the 1914 Kentucky Derby the morning headlines shouted 'Slow Track for the Derby.'

The 4-to-5 favorite Old Rosebud brought dazzling form into the race having won 10 consecutive starts, each in dominating fashion.

Old Rosebud continued his brilliant ways and made an absolute mockery of his Kentucky Derby opposition. He won by eight lengths and did it while “under hard restraint” according to the result chart. In the history of the race, no horse has ever won the Kentucky Derby by a wider margin. 

Indeed, Old Rosebud beat some quality horses in the Derby. Runner-up Hodge would win the Clark Handicap over the same track in each of the next two years. Third-place Bronzewing had won both the Ashland and the Blue Grass Stakes in her two starts before the Kentucky Derby. She returned to Churchill Downs two weeks later to win the Kentucky Oaks. Secretary Garret D. Wilson of the Kentucky Association would later tell Daily Racing Form: “Bronzewing is the best filly I have seen in twenty years.” Yet both she and Hodge were obliterated by Old Rosebud, and it was 13.5 lengths back to the fourth-place finisher and 20 lengths back to fifth. 

Most impressively, over a track widely predicted to be slow, Old Rosebud's final time of 2:03.4 shaved 1.4 seconds off of the track record, and his record stood for 17 years.

Old Rosebud actually won the 1914 Kentucky Derby in a faster time (2:03.40) than California Chrome did in the 2014 edition (2:03.66), which is pretty remarkable considering how much slower final times were a century ago. For instance, the two six-furlong races on the 1914 Kentucky Derby card went in 1:14 and 1:13.40. In 1914, the Churchill Downs track record for six furlongs was 1:11 flat. On the 2014 Kentucky Derby card, a Maiden Special Weight race won emphatically by future stakes winner Masochistic went in a sizzling 1:08.85. I suppose that performance could make a list for top “putover jobs” in Kentucky Derby undercard history.

Unfortunately, Old Rosebud broke down in his very next start. But, in one of the great romances in horse racing history, he returned to the races as a six-year-old, off of an almost three-year layoff.  He won 15 of his 21 starts that season and was considered the undisputed Horse of all Ages. Nicknamed both “The Courageous Cripple” and “Old Buddy,” this horse is more famous for his sensational comeback at age 6 than anything else, but his Kentucky Derby win was truly an unbelievably great performance.

1931 Twenty Grand

In 1931, the Preakness was run a week before the Kentucky Derby. It was widely expected to be a showdown between Twenty Grand and Equipoise. However, as you can see from the official chart, these two horses endured troubled trips and were defeated.

The handicapper's post-race write up stressed the severity of trouble both horses faced, and clearly indicated that runner-up Twenty Grand actually endured even more trouble than fourth-place finisher Equipoise.

Equipoise was sidelined after the Preakness and would eventually win his next seven starts after that defeat, including a Met Mile victory. He is credited for being the Horse of the Year at both ages four and five.

In Twenty Grand's next start, he came from off the pace to win the Kentucky Derby by four lengths, winning under wraps, in the dazzling time of 2:01.80. Twenty Grand shaved 1.40 seconds off the previous track record. Yes, the track was playing quite fast that day: one race earlier, the good four-year-old Gallant Knight (who was 2nd to Gallant Fox in the previous Kentucky Derby) ran 6 ½ furlongs in 1:16.20. But, everything about Twenty Grand's Derby win was impressive. Even though he only won the race by four lengths, he left the field scattered behind, with daylight margins between each runner.

In what was hyped as a major showdown, Twenty Grand faced off against two-year-old Champion Jamestown in the Belmont Stakes:

The match-up simply didn't live up to the hype, as Twenty Grand won the Belmont Stakes by 10 lengths “in a canter” according to the chart.

He added the Travers Stakes later in the year, crushed that season’s champion older horse Sun Beau by 10 lengths in the Saratoga Cup and won the Jockey Club Gold Cup at odds of 1-to-50 ($2.04) to complete one of the greatest three-year-old seasons ever.

Twenty Grand broke down in his second-start as a four-year-old after a winning return, retired to stud, and proved to be sterile. Like Old Rosebud before him, he was asked to make an almost three-year layoff when he returned to the races at age seven. His dramatic comeback was a failure. However, if you trust the written post-race accounts of the 1931 Preakness, Twenty Grand could easily have been a Triple Crown winner. One thing is for sure, he crushed his opposition in a great effort in the 1931 Kentucky Derby.

1941 Whirlaway

In a performance that many observers felt was unbelievable, Whirlaway won the KY Derby by 8 lengths in track record time of 2:01.40.

Second-place finisher Staretor returned to Southern California after the Kentucky Derby and finished first in his next 3 starts, including a Hollywood Derby win at ten furlongs before an injury sidelined him.

Third-place finisher Market Wise (beaten 8.25 lengths) came into the Derby 4-for-4 lifetime in routes and was a last-out Wood Memorial winner. He was later a co-champion older male.

Fourth-place finisher Porter's Cap (beaten 10.5 lengths) won the Santa Anita Derby by 4 lengths and was an easy winner of the Chesapeake Stakes in his Eastern prep for the Derby.

Fifth place finisher (beaten 11.5 lengths) Little Beans came into the race with seven wins from 11 starts and three other placings with his only off-the-board finish the result of a DQ in a race where he finished first.

The Flamingo winner Dispose finished sixth. A last-out six-length Blue Grass winner Our Boots finished eighth. Simply put, Whirlaway scattered a very good field in record time, and he did it with an explosive stretch burst. The final quarter-mile of the 1941 Kentucky Derby was run in 24 seconds flat, and Whirlaway was more than two lengths behind with a quarter mile to go, he surely ran his final quarter in under 24 seconds, while drawing off under wraps.

Whirlaway, of course, went on to win the Triple Crown.

1955 Swaps

In 1955, Swaps scattered an outstanding Derby field in the excellent final time of 2:01.80 over a track that wasn't yielding particularly fast times on the card.

The great Nashua was well placed and had every chance to reel in the California bred star, but he could only manage to finish a valiant second, beaten a length and a half. It was eight lengths back to a very good three-year-old Summer Tan, who finished third with no excuse. Meanwhile, Racing Fool, who brought a four race win streak into the Derby, including the Blue Grass, was fourth beaten 12 lengths with no excuse.

Simply put, this was a devastating front-end victory by Swaps. Instead of continuing on with the Triple Crown series, he returned home to California and won four straight Stakes races before being defeated by Nashua in a match-race. Nashua captured the Preakness and Belmont as well as a slew of other important races en route to being recognized as Horse of the Year in 1955. Swaps would earn that honor as a 4-year-old in 1956.

1973 Secretariat

In an absolutely incredible performance, “Big Red” blitzed his final quarter mile of the Derby in 23.20 seconds and left an excellent field scattered behind him. Sham was beaten 2 ½ lengths. Our Native was third beaten 10 ½ lengths. Forego was fourth beaten 12 lengths. The final time for the race was an unbelievably fast 1:59.40—a track record that stands to this day.

Secretariat's Derby performance is so widely regarded as one of the best in the history of the race, that few words are even needed to justify its place on this list.

1979 Spectacular Bid

The opening quarter mile in the 1979 Kentucky Derby was run in 24.20 seconds and the speedy Spectacular Bid was positioned all the way back in seventh. Going into the race, a few rival trainers felt Spectacular Bid might not be able to see out the ten furlong distance. His dam was a sprinter on the fair circuits in California, and here he was positioned ten lengths off the early lead at the first call.

How slow was that opening quarter by Kentucky Derby standards? You have to go all the way back to 1912 to finder a slower opening quarter in the Derby, when a horse named Worth got away with a 24.60-second opening quarter on a track labeled as “muddy”. Worth held on to win gate-to-wire in the comically slow final time of 2:09.40 over an obviously deep surface.

It was a high-quality horse in General Assembly who set the slow opening quarter in Bid’s Derby, but it didn’t matter. Spectacular Bid easily erased the ten-length deficit and powered away to a clear victory as the 3-to-5 favorite. General Assembly, benefiting from the soft opening quarter, finished second. He was a good horse, and he later went on to capture the Travers Stakes by 15 lengths in the still standing Saratoga track record time of two minutes flat, but General Assembly was trounced every time he faced Bid.

Students of speed figures know that horses rarely run very fast numbers by closing into soft early paces. However, the Ragozin figure for Spectacular Bid’s Kentucky Derby win came back a stunning 1.75. At the time, it was the second-fastest Ragozin ever run in the Derby, only trailing Secretariat’s 0.75.

The Southern California superstar Flying Paster, thought to be Spectacular Bid's most dangerous rival, tried to go with The Bid on the far turn and was thoroughly outclassed. Here are the PPs for Flying Paster going into the 1979 Derby, where he finished fifth beaten ten lengths.

Doug Salvatore is a professional horseplayer who writes on handicapping topics for and tweets @DougieSal