Kentucky Oaks and Kentucky Derby Preview

Table of content:

I.Official Post Times Read More
II.Kentucky Oaks Preview Read More
III.Kentucky Derby Read More
1.Odd facts on track Read More
2.Past WinnersRead More
3.Top 5 JockeysRead More
4.Top 3 TrainersRead More
5.Kentucky Derby Preview Read More

I. Official Post Times

Post times have been released for the Kentucky Oaks and Kentucky Derby and they are as follows:      

  • Kentucky Oaks will be at 5:45 pm track local.
  • Kentucky Derby will be at 7:01 pm track local.

II. Kentucky Oaks Preview

The first Kentucky Oaks took place on May 19, 1875, and was modeled after the British Epsom Oaks. At that time Churchill Downs was known as the Louisville Jockey Club. The Oaks and Derby are the oldest continuously contested sporting events in American history.  Surprisingly enough the Kentucky Oaks is one of the most heavily attended sporting events in all of America, and surpasses the attendance of the Belmont Stakes and Breeders’ Cup almost every year. Normally it is the kick-off leg of the Filly Triple Crown which is then followed up by the Black Eyed Susan at Pimlico and the Acorn Stakes at Belmont Park.

In 2009 Rachel Alexandra absolutely destroyed the record of largest winning margin when she rolled to a 20 length victory. Rachel Alexandra would then skip the Black Eyed Susan and race in the Preakness Stakes and win, beating the Kentucky Derby Winner Mine That Bird.

Rosie Napravnik, in 2012, became the first female jockey to win the Kentucky Oaks when she was able to the victory aboard the aptly named Believe You Can at a nice price of 13-1. She would then win the Oaks again in 2014 aboard Untapable who ran the fastest time since 2003.

This is an odd year obviously for the Kentucky Oaks since it will be run in September. There is also a chance that some of the top jockeys are unable to ship to Churchill Downs in order to ride their mounts for the Oaks or Derby. There are many factors to keep in mind when handicapping that race, but with that being said…

Direct to Kentucky Oaks

Here is a look at the prospective field for the 146th running of the Kentucky Oaks:

Swiss Skydiver
Swiss Skydiver

1.       Swiss Skydiver – Trained by Kenny McPeek and ridden by Tyler Gaffalione. Swiss Skydiver will very likely go off as the favorite in this race. She has 5 wins in 9 career starts, and has really improved as a 3 year old filly. She won the Grade 2 Fasig-Tipton at Gulfstream Park, and then followed that up with a Grade 3 win in the Fantasy Stakes. Once Santa Anita returned to racing action she won the Santa Anita Oaks by 4 very easy lengths over Speech. Most Recently she had a monster performance in the Grade 1 Alabama Stakes which was the perfect prep race for the Kentucky Oaks where she has beaten most of her competition already.

2.       Gamine – Trained by Bob Baffert and ridden by John Velasquez. Gamine will surely be the main competition to Swiss Skydiver, and this race has the potential to be an epic match race between the 2 fillies. Gamine has lost only once, and even in that race she crossed the line first, but then was disqualified. On Belmont Stakes day Gamine ran in the Grade 1 Acorn Stakes, and proceeded to win that race by only 18 lengths. It is the best performance of any 3 year old filly to date, but the field that day was a weak field. Then Gamine backed up that performance by dispatching of Venetian Harbor by 7 lengths in the Grade 1 Test Stakes.


3.       Speech – Trained by Michael McCarthy and ridden by Javier Castellano. Speech has won 3 of 7 career starts, and hasn’t finished worse than 3rd yet. Most recently she was victorious in the Central Bank Ashland Stakes at Keeneland. She beat Venetian Harbor and Bonny South that day. However, she wasn’t able to keep up with Swiss Skydiver in the Santa Anita Oaks so she will need to take a big step forward on Oaks Day if she wants to contend against the likes of Swiss Skydiver and Gamine.

4.       Venetian Harbor – Trained by Richard Baltas and ridden by Joel Rosario. Venetian Harbor really enjoys coming in 2nd place. In 6 career starts thus far she has 4 second place finishes, and two wins. That is normally a great track record to have, however in this case she has been beaten by Swiss Skydiver, Gamine, and Speech. When she was victorious in the Las Virgenes it looked as though she would be one of the favorites in the Kentucky Oaks, but none of the horses in that field materialized and Venetian Harbor hasn’t been able to stick with the top horses in the division as of yet.

Venetian Harbor with jockey Flavien Prat
Venetian Harbor with jockey Flavien Prat

5.       Shedaresthedevil – Trained by Brad Cox and ridden by Florent Geroux. Shedaresthedevil is a very consistent Filly who does have 4 wins on the resume. The issue is those wins are light on competition. This is a large step up in class for this filly after her win in the Indiana Oaks. It was a nice win on looks, but the speed figures came back soft and once again the field was light. She will need to improve greatly in order to win.

6.       Bonny South – Trained by Brad Cox and ridden by Irad Ortiz. Bonny South won 3 in a row and was improving with each start before finishing 4th in the Ashland Stakes. Her best race to date was the victory in the Grade 2 Fair Grounds Oaks where she was able to pull off a 6-1 upset. She then went to the Alabama Stakes to face Swiss Skydiver and ran a very solid 2nd place in that race, but was no match Swiss Skydiver in that one. She should get a nice trip and fast pace to run into, but again is another one who’ll have to improve.

7.       Tonalist’s Shape – Trained by Saffie Joseph and ridden by Irad Ortiz. Tonalist’s Shape has 6 wins in 8 starts so far in her career and two of those were graded stakes victories. Her most impressive victory was in the Grade 2 Davona Dale Stakes at Gulfstream Park where she beat Spice is Nice by just over a length. That race also provided her highest speed figure to date. There are two races of concern though, as she finished in 7th as the favorite in the Grade 2 Fasig-Tipton. She didn’t have any excuses in that race, and again in the American Oaks at Saratoga where she finished in 4th in just a 5 horse field.

Direct to Kentucky Oaks

III. Kentucky Derby

The 2020 Kentucky Derby will take place on the First Saturday in…September. Unfortunately, due to the global pandemic this years Kentucky Derby was postponed from its normal spot in May and rescheduled for September 5th. This is the first time since 1946 the race will not be held on the “first Saturday in May”. Also, for the first time ever there will be no spectators at the Kentucky Derby which was just announced last week.

The Kentucky Derby has a long and storied tradition dating back to 1875. It is without a doubt the most prestigious American horse race. In a normal year the Kentucky Derby would attract 150,000 spectators, and wagering would set records. In 2015 $194.3 million in total wagers were made with $23 million coming from on-track wagering. More than 1,200 international simulcast wagering outlets co-mingled money into the Churchill Downs betting pools.

Direct to Ante-post Market – Kentucky Derby

1. Odd facts on track


• 127,000 Mint Juleps sold (made with Kentucky bourbon, simple syrup,

crushed ice, powered sugar and mint)

• 40,000 Oaks Lilies sold (vodka, cranberry juice, triple sec and sweet and sour)

• 5,000 liters of bourbon drank

• 13,000 glasses of G.H. Mumm champagne drank

• 475,000 pounds of shaved ice for Mint Juleps & Oaks Lilies consumed

• 2,250 pounds of mint (all locally grown)

• 300 crates of mint

• 522,000 cans of beer


• 163,000 hot dogs

• 22,000 barbecue sandwiches

• 14,000 pounds of chicken

• 11,000 pounds of New York Strip loin

• 11,000 pounds of turkey

• 43,600 jumbo shrimp

• 12,000 pounds of potatoes

• 1,100 gallons of salad dressing

• 2,350 pounds or 9,400 sticks of butter

• 2,600 gallons of dairy cream

• 2,200 gallons of assorted oils

• 49,000 Derby Pies

• 395,000 fresh berries

• Kentucky Proud – 14 different farmers, growers and producers supply

over 5 ½ tons of local products

• 1,000+ back of house cooks and support staff


• The Kentucky Derby is the oldest continuously held major sporting event

in the United States. It has been staged every year at Churchill Downs

without interruption since the inaugural running on May 17, 1875.

• The Kentucky Derby is run at 1 ¼ miles which is equivalent to 2,011.68

meters, 2,200 yards, 6,600 feet or 79,200 inches.

• This year’s Kentucky Derby will mark the 125th consecutive year that the

race has been carded at 1 ¼ miles. It was contested over 1 ½ miles from


• 1,234.5 feet is the length of the stretch from the head of the lane to the

finish line

• Has been run on the first Saturday in May every year since 1946.

• Record 170,513 in attendance at 2015 Kentucky Derby

• Record 123,763 in attendance at 2015 Kentucky Oaks

• Record 294,276 in combined attendance at 2015 Kentucky Oaks &

Kentucky Derby

• Since 2000, combined Oaks and Derby attendance has grown 13.5% from

259,360 to 294,276

• 11,500 working at Churchill Downs on Derby Day.

Direct to Ante-post Market – Kentucky Derby

2. Past Winners

Secretariat, Photo: TT

Let’s take a look at some of the past winners and memorable Kentucky Derby races in history.

  • 1875 the very first Kentucky Derby winner was Aristides ridden by Oliver Lewis and trained by Ansel Williamson. Not surprisingly I do not have any video of this race.
  • 1882 Apollo wins the Kentucky Derby, and in doing so became the first Derby winner to pull the feat off without racing a 2 year old. This is significant because until Justify won the Kentucky Derby in 2018 that feat had never been repeated.
  • 1915 the first filly to ever win the Kentucky Derby occurred when Regret was able to get the job done. They did not enter the filly in the Preakness Stakes, but she did rack up 6 career stakes wins before being retired.
  • 1919 Sir Barton becomes the first horse to complete the Triple Crown. Sir Barton beat a field of 12 going wire-to-wire and winning by 5 lengths. He then won the Preakness Stakes, and in odd fashion ran in the Withers Stakes between the Preakness and Belmont. He was able to win both of those with the last race completing the Triple Crown.
  • 1930 Gallant Fox becomes the 2nd Triple Crown winner under Earl Sande and trainer Jim Fitzsimmons.
  • 1937 War Admiral wins the Triple Crown, but is more known for being the rival of Seabiscuit during the Great Depression. War Admiral and Seabiscuit had a match race in 1938, and a movie made about Seabiscuit and that race.
  • 1948 Citation wins the Triple Crown and also in doing so wins 16 consecutive major stakes races and becomes the first horse to win $1 million in earning.
  • 1973 Secretariat the most famous triple crown winner of all wins under jockey Ron Turcotte and trainer Lucien Laurin. More impressive than the Derby win was the Belmont Stakes victory. Secretariat set the speed record that day and it still stands. He won the Belmont by a 1/16 of a mile. Of course there was also a movie made about Secretariat.
  • 1978 saw probably the best rivalry that horse racing can provide. Affirmed vs Alydar. Alydar was the 6-5 favorite in the Kentucky Derby and Affirmed was the 9-5 second choice. Affirmed was able to win the Derby by a length. The two then met up in the Preakness with Affirmed beating Alydar by just a neck. Finally, they met in the Belmont Stakes and they were neck-and-neck the entire stretch with Affirmed getting his nose down at the wire to win the Triple Crown.
  • 2004 Smarty Jones wins the Kentucky Derby, and looks poised to break the 26 year drought of no Triple Crown winners. He was able to win the Preakness, but in the Belmont Stakes he was ran down in the final stretch by Birdstone for a heartbreaking defeat. The Triple Crown drought would continue.
  • 2015 American Pharoah finally breaks the drought with dominating victories in all 3 phases of the Triple Crown. In the Kentucky Derby Victor Espinoza defeated Firing Lane late in the stretch to win by a length. In the Preakness Stakes he very easily dispatched the field over a sloppy track. He was able to win by 6 lengths over longshot Tale of Verve. Lastly, in the Belmont Stakes American Pharoah broke the 37 year drought beating Frosted rather easily.
  • 2018 saw Justify become the first horse since Apollo in 1882 to win the Kentucky Derby without having raced as a 2 year old. He did one better than that though as he went on to win Triple Crown giving us two Triple Crowns in 4 years.
  • 2019 was probably the most controversial Kentucky Derby we have ever had. Maximum Security the favorite and a Triple Crown hopeful was able to win the race, however immediately after the race finished the riders of Country House and Long Range Toddy lodged objections against Maximum Security. After a 20 minute inquiry into the race it was eventually determined that Maximum Security would be disqualified and Country House who ran 2nd at odds of 65-1 would be placed first.

Direct to Ante-post Market – Kentucky Derby

3. Top 5 Jockeys

Tyler Gaffalione
Tyler Gaffalione, Photo: TT

1.       Jockey Tyler Gaffalione – Tyler usually rides at Gulfstream Park, and has more than $8 million earnings so far in 2020, and placed in the top three 47% of the races he has ridden in. He has 859 mounts so that is an impressive statistic. He also has 154 wins this year. He will be riding longshot #8 South Bend.

2.       Jockey Ricardo Santana Jr – Ricardo Santana who generally rides at Oaklawn Park and Churchill Downs has had a very good year. In 662 mounts he has 115 wins, and has finished in the top three 43% of the time. He has $8 million in earnings in 2020 as well. He will be riding #2 Max Player.

3.       Jockey Manny Franco – Manny exclusively rides in the NYRA circuit which consists of Aqueduct, Belmont, and Saratoga. Manny has 100 wins 650 starts, and has $7.5 million this year in earnings. He also gets to ride the heavy favorite Tiz The Law here in the Derby.

4.       Jockey John Velazquez – John Velazquez will be riding Authentic in the Derby. He has only 77 wins in 457 starts, but still has $5 million in earnings. John Velazquez also has $420 million in career earnings as well has 6,228 wins.

5.       Javier Castellano – Javier Castellano will be on longshot Money Moves for trainer Todd Pletcher. Castellano has the highest percentage of finishing in the top 3 than any other jockey in this field. He hits the board in over 50% of his rides, which has been 460 this year. He has over $6 million earnings and 74 wins.

4. Top 3 Trainers

Trainer Steve Asmussen
Trainer Steve Asmussen, Photo: TT

1.       Trainer Steve Asmussen – By far the best trainer earnings wise in this Kentucky Derby field. He has $13 million in earnings so far this year, and the next closest trainer has $8 million. He has 272 wins, and his horses hit the board 47% of the time. He is the trainer #2 Max Player.

2.       Trainer Bob Baffert – One of the best trainers in the games for decades, and he brings in 2 horses to the Kentucky Derby. He is training #18 Authentic and #10 Thousand Words. His horses finish in the top three an incredible 63% of the time including a field best 30% winning percentage.

3.       Trainer Barclay Tagg – Only has had 48 starters this year, however he has over $2 million in earnings. His horses have finished in the top 2 almost 50% of the time, and he trains the best horse in the field Tiz The Law.  

5. Kentucky Derby Preview

Now that we’ve gotten all of the fun information out of the way. Here is the preview for the top horses in the field for the 2020 Kentucky Derby. We will likely still have 20 horses going to post, and in this section we will highlight a few of the main contenders.

Tiz the Law
Tiz the Law

1.       Tiz The Law – Trained by Barclay Tagg and ridden by Manny Franco. Tiz The Law is very easily the most dominant horse in racing right now. He will go off as the favorite in the Kentucky Derby, and will be very difficult to beat. He has won 6 of 7 starts so far, and entering his 3 year old here he has been nothing short of incredible. His 3 year old campaign started off at Gulfstream Park in the Grade 3 Holy Bull Stakes. In the Holy Bull he was able to easily dispatch of Ete Indien and Toledo when cruising to a 3 length victory. He then stayed at Gulfstream to race in the Grade 1 Florida Derby where he cruised to yet another victory. Those 2 races had questionable fields, and it seemed like Tiz The Law still had something to prove. He then went to New York to race in the Belmont Stakes, and looked superb winning by 4 lengths over Dr Post and Max Player. Finally, his last prep race for the Kentucky Derby was the Travers Stakes at Saratoga. Once again it was another special performance by Tiz The Law winning by 5 lengths without really every trying. There will be a few other contenders, but no other is going to sport this kind of resume or look as good as he has thus far on the race track.

Art Collector
Art Collector, ridden by jockey Brian Hernandez Jr.

2.       Art Collector – Trained by Thomas Drury and ridden by Brian Hernandez Jr. Art Collcetor is a perfect 4 for 4 in 2020. We aren’t entirely sure what this horse has yet, but the last 3 races have looked really good. Two starts back he was victorious in the Grade 2 Toyota Bluegrass at Keeneland, and then followed that up with a victory in the Ellis Park Derby. The victory in the Bluegrass was notable as he defeated Swiss Skydiver who as stated in the Oaks Preview is a very promising 3 year old filly and likely favorite in the Kentucky Oaks. Many thought Swiss Skydiver could easily hold her own in the Kentucky Derby had they chosen that spot. The Ellis Park Derby was light on competition but was the perfect prep race for Art Collector who heads towards the Derby as one of the few choices to contend with Tiz The law.


3.       Authentic – Trained by Bob Baffert and ridden by Mike Smith. Authentic hasn’t done much wrong yet in his brief career. His only loss was a 2nd place finish to Honor A.P, a fantastic horse in his own right, and has 4 wins to accompany that 2nd place finish. The latest win was in the Grade 1 Haskell Stakes at Monmouth Park. That field also included Derby hopefuls Dr. Post and NY Traffic. It’s tough what to make of that race though, as Authentic looked as though he should’ve easily won that race but really struggled to get by NY Traffic down the stretch eventually winning by just a nose. For me that performance raised more questions than answers and it will be interesting to see how the horse is bet on Derby Day. It will also be interesting to see who Jockey Mike Smith chooses to ride.

Honor AP
Honor AP and jockey Mike Smith

4.       Honor A.P. – Trained by John Shirreffs and ridden by Mike Smith. It is unknown which horse Mike Smith will ride in the Kentucky Derby, but he has 2 great options between Authentic and Honor A.P. Given that Honor A.P. beat Authentic in the Santa Anita Derby that could play a factor into the decision, but we will see. Honor A.P. looked great when winning the Santa Anita Derby, and then came back less than 2 months later and ran poorly when finishing 2nd to Thousand Words in the Shared Belief Stakes. That loss certainly made people take a step back and re-evaluate this horse. He has been working out very well at Del Mar prior to shipping to Churchill Downs and Mike Smith was the jockey who has been working him out as well.

5.       King Guillermo – Trained by Juan Carlos Avile and ridden by Samy Camacho. Just 2 wins in the career so far, but did win the Tampa Bay Derby. He also had a very respectable showing in the Arkansas Derby when finishing 2nd to Nadal, who would’ve been a factor in the Derby if it wasn’t for an injury. The Tampa Bay Derby caught everyone by surprise as he was sent out of the gate at 50-1. He was able to stalk just off the pace, and ended up winning by 4 lengths over Sole Volante. The Arkansas Derby race proves that was not a fluke run, and depending on how he is drawn in the field he will likely sit close and get another nice trip. He will have to run better than he has recently in order to make up the ground on Tiz The Law, and some others.

King Guillermo, and Jockey Samy Camacho
King Guillermo, and Jockey Samy Camacho

6.       Dr Post – Trained by Todd Pletcher and ridden by Joe Bravo. Dr Post only had one race as a 2 year old and it was a 4th place finish. His first race as a 3 year old was a maiden breaking score at Gulfstream Park. He then ran a big race in the Unbridled Stakes at Gulfstream Park which propelled him to the Belmont Stakes. In the Belmont he tried to chase down Tiz The Law, but was ultimately no match in that one. He tried to do the same to Authentic in the Haskell and was once again just not good enough to get it done. Hard to believe something drastic changes and he’s able to reverse the form against those 2.

7.       Thousand Words – Trained by Bob Baffert and ridden by Abel Cedillo. Started the career off 3-3 before losing to Authentic and Honor A.P. in the San Felipe. He was bet heavily as the 2nd favorite in that race, but just got never close enough to the front to be a factor. Fast Forward to August 1st, and he races against Honor A.P. again, but this time goes right to the lead and never looks back scoring a 9-1 upset over Honor A.P. It is hard to tell which tactics will be employed for the Derby especially without knowing which post they will be starting in. However, there is a lot of speed in this race and Thousand Words isn’t likely to be on the front end which is how he was able to win the Shared Belief.  

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