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The Kentucky Derby is the longest-running, continuously held sporting event in the United States, spanning over 150 years. Along the way, the race offers a snapshot of American history and culture. From the beginning, the race has a wide variety of owners, trainers, jockeys, and associated people that run the gamut of character, wealth, and morality. There are around 15,000 foals born every year, and all breeders would love to run in the Derby. Approximately 150,000 people are expected to watch the race, which is worth $5 million. Only 20 horses enter the gate, and only one group connected to the winner gets to celebrate. In the end, around two minutes after the 6:57 PM post time this Saturday, the fastest horse will win, just as it has been since 1875.
This year’s winner must have racing luck, and the best horses (breeding and confirmation) are SOVEREINTY and JOURNALISM. My friends in the know say they are training exceptionally well, and their connections feel strongly about a victory. One of the better horses, TAPPEN STREET, had a dream deferred with an injury over the weekend. The 21st horse drew into the race, and BAEZA continued to train and get ready at Churchill in case another top 20 horse pulled out. BAEZA is one of the country's best 3YO’s, and his dam produced two winners of the Triple Crown. He doesn’t have enough points and may have to wait for The Preakness.
From the Jockey’s Perspective - How Will The Race Go?
From the backstretch to the owner’s box, it is said “the pace makes the race” and “time only matters in jail.” They are conflicting statements, yet both are true. These are things to keep in mind when attempting to handicap the top finishers of the Derby. Studying the form and picking the top few horses from 20 of the best 3YO’s in the country is not an easy task. As with most things in life, if you enjoy the process and don’t try to focus on the outcome (Let Go and Let God), the handicapping of the Derby is a fun life pursuit.
When I review a race, I try to focus on the macro view and then delve into the particulars of how things unfold. The post positions are drawn randomly with dice, and each horse may have an ideal post position. Generally, you don’t want to be on the way outside or trapped on the inside rail. If I had tactical speed, I would like post 5-10. The most successful post is #5, with ten wins, and #17 is the worst, with NO wins in history. Arthur Hancock makes a great point about the actual handicap of an outside post (not much), but the snake-bitten, black cat post of #17 is death if you ask me.
This year’s Derby should feature 5-speed horses that ensure a fast pace, which will likely set up for closers. The speed will tire around the far turn and cause traffic problems for late closers. Tired horses tend to drift to the rail, causing bottlenecks. Mid-pack horses and jockeys wait on the outside and try to go slower around the turn to jam up the pack behind the tiring speed horses. A wide trip may be the better path, and getting through on the rail, like MYSTIC DAN (below), is a risk many would forgo in favor of a clean trip. Godolphin Stables has the talented EAST AVENUE that should be in the Pat Day mile on the undercard, but they want a fast pace for their favorite SOVEREIGNTY. EAST AVENUE is called the “rabbit” for his stablemate SOVEREIGNTY and must ensure there is a fast pace. His jock will follow orders if he wants to ride for Godolphin again. There is speed on the inside and outside posts (CIT BULL, NEOEQUOS, RODRIQUEZ, ADMIRE DAYTONA and OWEN ALMIGHTY). BAEZA is on the waitlist to get into the race and could draw in on Saturday morning by 9 AM if there is a scratch. He should be in the Derby, but the new point system is flawed and will likely be corrected next year. There is too much speed in the race not to believe they will cook themselves and set it up for a closer.
The first turn in the Derby is unlike any other race in the world. It reminds me of the Palio in Siena. There is tons of traffic, and it could ruin a horse’s chances if he gets shuffled back in the first 2 furlongs of the race. A thrifty, athletic horse like COAL BATTLE is well suited to adjust and weave in and out of traffic. The class of the field, JOURNALISM, will break from the 8-hole and will try to get to the outside when he crosses under the wire the first time to avoid traffic. His inexperience and the small fields in California are negatives he must overcome to win. If he is as good as people say, it will be fine. Another thing I find refreshing about the Derby is when horses with no breeding run well. A horse doesn’t know what he was sold for, and if they have the grit and determination, they can outrun their breeding. In my opinion, people are the same. CHUNK OF GOLD sold for $2,500 eighteen months ago and has won $350,000 and could win the race. I think of the money I’ve spent over the years for the Derby Superfecta, and I could have bought a lot of horseflesh with better success. CHUNK’s trainer, Ethan West, is 32 and got in the game because of his grandfather. West learned the business “brick by brick,” and it would be a remarkable Cinderella story of CHUNK wins. SANDMAN should benefit from the fast pace and has an ownership group that wins races; however, he is in the “black cat” #17 post.
The 2nd and 3rd quarters of a mile are critical for the race. BAEZA’s half-brother MAGE won the Derby because Mike Smith allowed future Belmont winner PALICE MALICE to go 45.3 and 1:09.8 for the 3/4 miles. Too fast. If they run under 1:10 on Saturday, the closers will come from far back, very late in the race. BURNHAM SQUARE should benefit, and Hernandez is an excellent rider for Churchill. TIZTASTIC and PUBLISHER will be right there and Asmussen should have a chance at his Derby, if the Rory mojo continues in American sport. of the two Japanese horses in the race, I like LUXOR CAFE and the race may set up well for him coming from the 7 post. It is the 10 anniversary of FUSACHI PEGASUS winning the Derby. GRANDE should run well and improve, and owner Repole (Featured on Netflix show) has been trying to win this race for years. He spent ~$15M by himself or in partnership in 2023 for the most part, to win the Derby in 2025. Let’s see if he can buy himself a Derby…but I am betting against it.
I think they will run the 3/4 mile in 1:10 or faster, and this will set up well for mid-range closers who can get to the outside at the start of the backstretch. Those jockeys should sit on the outside and have everyone jam up the inside behind tired horses at the 3/8th pole, around the final turn. It is an unwritten rule for jockeys on tired horses to shut down the rail and not let others through. A jockey should ride “only one horse” but Rispoli, Hernandez, Johnny V, Ortiz and Rosario on JOURNALISM, BURNHAM, GRANDE, SANDMAN and SOVEREIGNTY will be riding shotgun on the competition, hoping to negatively impact their trip. They will be watching to see who is moving first and if they can keep someone pinned in behind tiring horses. The jockey and horse that can be in the best position at the top of the stretch will win. If you are held back, it is really difficult to make up ground unless you are significantly better than others. The top 4-6 horses should be around the same and if so, the trip will make the difference. Given the outside post of SANDMAN and SOVEREIGNTY, they should have a good trip even if they go wide.
Predicting the winner on a Grade 1 horse race is different than the Derby. In a typical race, the best horse usually wins. Because the Derby has 20 horses and 150,000 people, it is a race like no other and the horses know it. So much luck is involved. On paper, the top horses should have no problems. The reason why I like the Derby, is the “Derby Factor” puts a huge unknown on the outcome and ANYTHING can happen. Good luck!
2025 Kentucky Derby - Order Of finish:
SOVEREIGNTY - beautiful horse, Mott is a great trainer and says this is his Derby horse ever. Needs the fast pace to crumble the field.
JOURNALISM - Well bred and won big time races, should
SANDMAN- Tapit colt will come running late
BURNHAM SQUARE - He is tactical and should be athletic and get a good trip.
The Jockey and Best Trip wins
I am often asked how much difference the rider makes in a race. For the most part, the top jockeys are all so good there is very little noticeable difference. Then, every now and then, there is a ride that helps so much that the jockey is 100% responsible for the win. For a long time, I thought P Val’s winning ride in the Preakness when SUNDAY SILENCE beat EASY GOER was one of the best rides ever. In last year’s Derby, Brian Hernandez rode the most impactful race I’ve ever ever seen. A fearless display that rewarded him with a nose victory. Below is a picture showing him putting his horse in a very tight spot. If MYSTIC DAN had clipped heels or tripped, he somersaults and falls, taking out many other horses and jockeys. It can happen and is part of the sport.
It will be interesting if another jockey can position himself to take advantage and win the race with a horse that isn’t the fastest.
The Wager
I suggest teaming up with friends to form a syndicate and bet the exotic Derby bets including the Win, Place, Show, Exacta, Trifecta, Superfecta (impossible) and the Oaks / Derby Double. You can get complicated or bet a few horses to win at different amounts, say, more money on a lower-price horse and less for a longer-odds horse.
The PPs are listed below; print them out and review them.
I am too old to change my course. I am betting on the Superfecta with a fun group. The pool has been $2.5-$3 million over the past five years. All tickets with winning combinations will split the pot. In 2024, there were approximately 350 winners, who received around $9,000 each. My group is trying to hit the “one-off” and would prefer that my group wins the ONLY winning bet. We don’t want to share the pot. It's not an easy task, and there are 116,280 potential winning numbers. The GIACAMO Superfecta paid $864,000 for a $1 bet. Only one person (or group) hit it. That’s what my group is shooting for. If we win, that will be the feature in my obituary, along with multiple Rim-to-Rim-to-Rim hikes in the Grand Canyon and, God willing, my sobriety since 12/18/04.
NEWS, VIDEOS, STORIES, ETC
Past Performances for the Kentucky Oaks and Kentucky Derby.
You can open an online betting account and do the daily double with the Oaks / Derby and also play any number of Derby bets. The Exacta and Trifecta are easier than the Superfecta.
Determined Stud Farm - Co-Owner of RODRIGUEZ and CITIZEN BULL
Matt Dorman, CEO of Credible Behavioral Health, a health IT company in the behavioral health industry, is making a real difference. Dorman started his breeding business in Maryland but moved the operation to Kentucky. He still owns the company in Rockville and has a property near Easton. Breeding two horses in the race is impressive.
Determined Stud - with small-time Maryland Roots - Unreal story
Maryland Hunt Cup - 2025 - ROAD TO OZ Wins
(13th Fence below) The race has remained unchanged for over 100 years. No sponsors and a $100,000 purse are all funded by parking revenue, which has a waiting list of over five years. Small-time Owner Dan Baker (Tate Engineering) and trainer Mark Beecher won the race. It's a great story about a horse that ran for the lowest claiming price in America ($5,000) and has now won two stakes races, including the American Grand National and The Maryland Hunt Cup. He may not be well-bred, and he couldn’t win a cheap claiming race, but boy, is he a talented horse running 4 miles and jumping ~5’ fences going 25 miles an hour. It is almost impossible to understand how to find a Hunt Cup horse, but when you do, they are worth their weight in gold. My friend Shockey Gillet (Master of Green Spring) bought the horse for $1,000 in the Calcutta, and I took $500 off of him. Then, I syndicated to Chad Meyer and Peter "Rat” Ratcliff for one-third of my action. I then became nervous on Saturday and split my equity 50/50 by selling to my cousin, Stew Strawbridge. My equity was $83, and we ended up with 12:1 odds, netting me $913. Not bad, but Rat and Chad did even better. I think Shock took some chips off the table, too, but it's not my place to share those details.
Don Alberto Farm and the Chilean family who bought it. JOURNALISM’s Breeders
Breeding and Sale Prices
The list of the sales prices for the Derby horses is below. Those with N/A are homebreds and never went to the market. Their cost was the Stud Fee, and the costs below range from $40,000 - ~$300,000 stud fees.
Just Another Day at M&T Bank in Hunt Valley, MD
As many people know, I run a syndicate for the Superfecta, which is likely a fool's errand, but a devoted group of friends try to hit it with me every year. Logistically, it takes some time because I receive money from many people, and then I withdraw everything from the bank a few days beforehand to place the bets on Kentucky Oaks Day. It ends up being a withdrawal of approximately $10,000, and withdrawing cash from the bank is no longer as easy as it once was. I was in the bank on Monday and walked in alone. I filled out a withdrawal ticket for $10,000 and the lady looked at me strangely. I would hope that I look like a professional business person and dress well, but every year, I think the bank branch either thinks I’m selling drugs or doing something suspicious. This year, the lady was examining my signature and wasn’t sure if she could do the entire withdrawal in one day, and it was taking some time. Then, a landscape guy walked in to make a small deposit, and shortly thereafter, a long-time family friend and prominent horse owner and breeder in the community came in to get something notarized. He saw me, and the landscape guy said I was causing a delay because I needed $10,000. The horse owner, who shall remain nameless, is aware of my Superfecta quest, replied, “Miss, for what he’s using that money for, you might as well light it on fire behind your counter!” She looked at me, then at him, and then grew very concerned, prompting me to sign a few more papers. The landscaper was also confused and I was laughing. When I got the money, I told her I would be back to tip her if we won a $300,000 Super. The friend/breeder will be one of the first calls I make if we hit! The list of calls to make if we hit the big bet has grown over the years but my Uncle Ned will be another call. Every year, he states, “You know Charlie, “A fool and his money are soon parted.” (Proverb 21)”
The Superfecta and If We Hit - I will be like the great Fred Sanford having “The Big One”
Pimlico Mornings - Watching the Derby winner train (May 15 and 16) - 6AM - 9AM
One of my favorite things to do is to bring families and young children to watch the Kentucky Derby winner train at Pimlico during Preakness week. I encourage you to do this and bring friends. It’s typically an early day, but we get to watch horses train and go to the jockey‘s room and see the Stakes Barn. Assuming all goes as planned, the grandstand will be demolished, and the entire facility will be rebuilt after this year‘s race. Come to Old Hilltop to witness the sunrise; it’s a truly unique experience. I’ve been doing it for 25 years, and now I see kids who came with their parents bringing their own young children. It’s something people remember for a long time, even if they only do it once. I will provide more information closer to the day. Email me with questions, and your kids will love it. Little Ottenritter came with his granddad when he was ~3 months old last year! Contact me directly with questions about parking. Please bring $5 cash for each pair of goggles.
Charlie your writing is from the heart and I enjoy reading these every year. Let’s hit it together with the rest of your friends this year.
So would you say the track itself is what makes the Derby difficult to predict and hard to win? Or the field of horses that shows up? Just curious and trying to understand 😊 thanks for writing!