Your Comprehensive Guide to Betting on the 2019 Kentucky Derby

The first Saturday of May is something American horse racing fan looks forward to every year. It is the traditional day of the Kentucky Derby, the first of the three Classics and marketed as the Greatest Two Minutes in Sports.

This legendary race takes place at the famed Churchill Downs track in Louisville and is a rapid 1m 2f race on a left-handed track on a dirt surface. It is also referred to as the Run for the Roses owing to the blanket of roses placed over the victor at the end of the race.


Best Kentucky Derby Betting Sites


The winner of the 2019 Kentucky Derby will receive a staggering purse of $1.86 million, and the 10 furlongs are covered at a breath-taking pace, with the winner usually covering the ground in a time of between 2:01 and 2:05. Geldings and colts carry 9-0 (126 pounds) while fillies carry 8-9 (121 pounds). The race is open to all 3-year old qualifiers, but only a select few have a hope of winning.

In this guide, I will briefly look at the history of the race, before checking out some trends to see if we can unmask the likely winner.

A Brief History of the Kentucky Derby

Not many people know the Kentucky Derby is the longest running sporting event in America. The first Derby was run in 1875 and has taken place annually every year since. Unlike the other Triple Crown races (the Belmont Stakes and the Preakness Stakes), the Kentucky Derby has never once been cancelled.

However, all three are incredibly endearing sporting events. All three horse racing Classics continued undisturbed during World War II – a testament to their popularity.

The story of the Kentucky Derby actually begins in 1872 when Meriwether Lewis Clark, grandson of famed explorer William Clark, paid a visit to Europe. When in England, he attended the Epsom Derby and became acquainted with the French Jockey Club while in France.

Inspired by his travels and his experiences of famous horse racing events, Clark decided to create a showpiece race in the United States. Henry Churchill gifted Clark the land to create a racetrack, and Clark formed the Louisville Jockey Club.

On May 17, 1875, Churchill Downs opened its gates for the first time and played host to the inaugural Kentucky Derby. Initially, the race was 1m 4f long and was only changed to its current 10-furlong distance in 1896.

While the first meeting was a big success, the track soon hit financial problems and was bailed out when a man named Matt Winn formed a syndicate and acquired the ground. Soon enough, Churchill Downs flourished again, and the Kentucky Derby became the great spectacle that Clark had hoped.

The term “Triple Crown” was only given to the winner of all three Classics in 1930 after Gallant Fox became the second horse after Sir Barton in 1919 to win all three in the same year. The existing order of the Classics, which has the Kentucky Derby first, the Preakness Stakes second, and the Belmont Stakes last, has been in place since 1931.

The race was first broadcast live on radio in 1925 and the first TV coverage occurred in 1949. The race was nationally aired for the first time in 1952. There was a scandal in 1968 when Dancer’s Image was stripped of the title after testing positive for an anti-inflammatory drug, the first and only winner to be disqualified.

While it is known as the fastest two minutes in sports, only two horses have ever run the race in 1:59:99 or less; Monarchos in 2001, and the all-time great Secretariat in 1973. The 1:59:40 time of Secretariat remains a record, almost half a century later!

The great Secretariat is also one of just 13 to win the Triple Crown. Last year’s Kentucky Derby winner Justify became the thirteenth horse to achieve this incredible feat. American Pharaoh was the twelfth in 2015, but there is a gap of 37 years dating back to Affirmed who was the eleventh horse to win the Triple Crown in 1978. Incidentally, Justify was the first horse since 1882 (Apollo) to win the Derby without ever having raced as a 2-year old.

As for records, Assault in 1946 was one of four horses to win by eight lengths which remains the largest margin of victory. Calumet Farm won eight Derbies from 1941 to 1968, while Ben Jones is the most successful trainer with 6 victories. Bill Hartack and Eddie Arcaro are the most successful jockeys with 5 wins apiece. As for the biggest outsider to win, that honor goes to Donerail who won the 1913 Kentucky Derby at odds of 91/1.

Useful Kentucky Derby Trends

The Derby has a larger field than most American races with a total of 20 horses. To qualify for the race, horses must compete in a series of 35 races around the world. The top 4 horses in each qualifying race receive points and the 20 top-scoring horses earn a spot at Churchill Downs.

Whether you are one of the 155,000 spectators in Louisville or are watching from somewhere else in the world, it will greatly help your selection process to have a few useful trends. Unlike many UK races where the field is not finalized until 48 hours before the race, we already know the Kentucky Derby field.

At the time of writing, Omaha Beach is the 4-1 favorite followed by Game Winner at 5-1 and Roaster at 6-1. Master Fencer and Gray Magician are the outsiders at 50-1 apiece.

Update: Omaha Beach and Haikal have both withdrawn from the 2019 Kentucky Derby. Omaha Beach had to withdraw due to a breathing problem discovered after developing a cough. Meanwhile, Haikal had to withdraw Friday morning with an abscess on front left hoof.

This makes Game Winner the new morning line favorite at 9-2. All horses will still wear the same program numbers, but post positions will shift a spot while Bodexpress draws in from the also-eligible list. The Kentucky Derby odds and positions chart below has been updated to reflect these changes.

Points Make Prizes

The existing points system is relatively new and was only introduced in 2013. All six winners since had earned at least 100 points. It is clear that trainers are now capable of focusing their horse with the specific goal of doing well in the Classics, and the Kentucky Derby in particular.

As it happens, only seven of the 20 horses have the necessary 100 points. Maximum Security, By My Standards, and Roadster all have exactly 100. Plus Que Parfait has 104, Vekoma has 110, Omaha Beach has 137.5, and Tacitus has 150. While the 2013 and 2014 winners were #1 in the rankings, none of the subsequent four winners were ranked first. Future Triple Crown winners American Pharaoh and Justify were ranked fourth and ninth respectively, but both had 100+ points.

Winner Last Time Out

The last eight winners of the Derby also won their previous race; three of them won the Santa Anita Derby that year while another two won the Florida Derby. All seven 100+ point horses won their previous race. For the record, Roadster won the Santa Anita Derby while Maximum Security took the honors in the Florida Derby.

100% Win Rate as a 3-Year Old

You have to go back to 2011 to find a Derby winner that wasn’t undefeated as a 3-year old. Plus Que Parfait was way off the pace in thirteenth in a race this season, while By My Standards and Vekoma were third in a race in 2019. Omaha Beach was beaten into second in this first race of 2019.

Therefore, the trends say we are down to three contenders: Maximum Security, Tacitus, and Roadster.

2-3 Season Runs

You have to go back to Smarty Jones in 2004 to find a Derby winner that didn’t race 2 or 3 times as a 3-year old before the race. All three remaining contenders fit the bill once again. Incidentally, Omaha Beach has raced four times in 2019 which is a second trend that the pre-race favorite doesn’t meet.

Final Race Winning Time

24 of the last 26 winners completed their final race in a time of below 1:51:00 over 10 furlongs, the same distance as the Derby. Maximum Security is the only horse to meet that trend but Roadster’s 1:51:23 in the Santa Anita Derby was impressive because of safety concerns which ensured the track was slow on the day.

Luck of the Draw?

In such a short race, the stall a horse is drawn in could prove crucial to its chances of victory. For example, no horse has ever won the Derby from stall 17 in 40 attempts, and that is where Roadster will run from!

In theory, horses drawn in the stalls close to the rails should have a great chance of victory. After all, it means less distance to cover. However, there hasn’t been a single winner from stalls 1-3 this century. For the record, War of Will is in stall #1, Tax is in stall #2, and By My Standards is in stall #3.

Horses in the middle of the field tend to perform well, but American Pharaoh won from stall 15 while Nyquist won from stall 13 in 2016. In practice, if a horse gets off to a good start and is travelling well near the front, the draw isn’t nearly as important as some people might think. While it is true that no horse has won from stall 17, has any previous runner with this draw possessed Roadster’s quality?

Latest Kentucky Derby Odds and Post Positions

With the race just days away, on-track oddsmakers have published the odds for every entrant. These are just estimates from the oddsmakers and each horse’s actual odds will ultimately be determined by the betting action on the day of the race.

Additionally, horse racing bookmakers outside the US offer their own fixed-odds prices for anyone wanting to put money down today.

Odds Post Position
Omaha Beach Scratched (was 4-1) 12
Game Winner 9-2 16
Roadster 5-1 17
Improbable 5-1 5
Maximum Security 8-1 7
Tacitus 8-1 8
Code of Honor 12-1 13
Win Win Win 12-1 14
Tax 20-1 2
By My Standards 15-1 3
War of Will 15-1 1
Vekoma 15-1 6
Spinoff 30-1 19
Plus Que Parfait 30-1 9
Bodeexpress 30-1 21
Cutting Humor 30-1 10
Long Range Toddy 30-1 18
Country House 30-1 20
Haikal Scratched (was 30-1) 11
Gray Magician 50-1 4
Master Fencer 50-1 15

Who Will Win the 2019 Kentucky Derby?

The trends mainly point towards Maximum Security. However, since the introduction of points, the favorite has won each race. Yet Omaha Beach doesn’t meet at least two winning trends and his trainer, Richard Mandella, is 0-6 in the Derby. Roadster is an interesting choice; not only is he an excellent horse, his trainer, Bob Baffert, has also won the race five times, including in 2015 and 2018.

Since the trends don’t fully align and point towards one winner; will there be an outlier? The points era suggests that a horse needs 100+ to be a contender but is a 6-year sample really enough to make a decision?

Vekoma is #3 in the points table, but the 20/1 shot has an unusual running style that many experts believe is unsuitable for winning the Derby. However, this is a horse with wins at Belmont and Aqueduct, so perhaps his odd style is part of his talent.

It is a wide-open field, but Improbable is a possible winner at 6-1. He was pipped by Omaha Beach last time out and has already enjoyed a 7.75 length victory at Churchill Downs over a mile.

However, many experts believe he is better off focusing on the Preakness. Win Win Win at 15-1 is an interesting outsider and is a danger if there is a hot pace. Tax is another interesting leftfield pick at 20-1 with Brisnet Speed Figures of 100+ in his last three races, the only horse in the field to do so.

Alas, it is likely that the Derby will be run at a less than lightning pace which will hurt the chances of Tax and Win Win Win. The smart money seems to be going with Maximum Security at 10-1, a horse that is a “potential freak” according to one oddsmaker, and of course, he meets most of the trends. Just how good he is will become clear on Saturday.

With two scratches as of Friday morning, the horses we’re watching have only become even more tempting – especially with former favorite Omaha Beach now out of the running.

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