Changing Paths: How the Road to the Kentucky Derby Has Changed the Path to the Triple Crown

Article by Jennifer Kelly

The Triple Crown has evolved into more than three historic stakes races; indeed, it dominates the first half of the racing calendar, driving the complexion of the three-year-old division and influencing both owners’ and trainers’ goals for their horses. The first of the three, the Kentucky Derby, has become the stuff of dreams, inspiring many owners of a young Thoroughbred to pursue their own piece of history. Preparing a horse for the first Saturday in May has taken on a new dimension with the addition of the Road to the Kentucky Derby points system. 

How much has this new priority affected trainers’ plans for their Triple Crown hopefuls? While trainers remained focused on preparing their horses to peak in late spring, how they get there has changed in the decades between the first eleven Triple Crowns and the 21st century’s two winners, a change that is both a result of and an influence on the approach to the Derby prep season. 

Path to the Crown

Preparing for a Triple Crown campaign over the last century has been as individual a pursuit as the horses themselves with the approach falling into a pattern in the later decades. Sir Barton went into the 1919 Kentucky Derby a maiden with no starts before his trip to Churchill Downs, a strategic move on trainer H.G. Bedwell’s part: the Derby had maiden allowance conditions at the time, which meant that the son of Star Shoot went to the starting line carrying twelve pounds less than favorites Eternal and Billy Kelly. 

Gallant Fox had only the Wood Memorial ahead of the Preakness Stakes, which came first in 1930. Counting that classic, the Fox had two races prior to his turn at Churchill Downs. His son Omaha was similarly tested in 1935; he opened his season with a win in a one-mile, 70-yard allowance before finishing third in the Wood Memorial at the same distance. War Admiral started 1937 with wins in a six-furlong allowance and then the 1 1/16-mile Chesapeake Stakes before heading to Louisville. 

The four Triple Crown winners of the 1940s were war horses not just because of the international context of that decade, but also because of their preparations for the triad of races. Whirlaway raced seven times at distances from 5½-furlong sprints to 1⅛-mile tests between early February and the first Saturday in May and all were in-the-money finishes as Ben Jones struggled to find a solution for the colt’s tendency to bear out on the far turn. Count Fleet echoed Omaha with his two starts in an allowance and the Wood Memorial, winning both. Assault started his path to Derby with three starts, a six-furlong sprint, the 1 1/16-mile Wood Memorial, and then the one-mile Derby Trial two days before the big race. Citation raced eight times in early 1948, finishing second only once, before his Kentucky Derby, starting with a six-furlong sprint in early February and stretching out to 1 1/8 miles twice. 

Secretariat’s path to Louisville went through a trio of races in New York, progressively lengthening the distance from seven furlongs in the Bay Shore to 1⅛ miles in the Wood Memorial. Seattle Slew had a similar preparation in 1977, stretching out from a sprint to nine furlongs, while Affirmed started four times, starting with a win in a 6½-furlong allowance, in California before coming west for his 1978 Triple Crown run. 

Keeneland Library Morgan Collection - War Admiral with C. Kurtsinger after winning Preakness Stakes 05.15.1937

Most of the first eleven winners prepared with races increasing in length as the first Saturday in May grew closer. While the number of races to get there varied by horse, that philosophy remained mostly unchanged, though now the need for points puts a heavier influence on the choice of prep races for potential Triple Crown horses. 

A New Approach 

Prior to 2013, the conditions for entry into the Kentucky Derby evolved from paying the entry fees to using criteria like graded stakes earnings to rank potential starters ahead of the first Saturday in May. The oversized 23-horse field in 1974 made it clear that the field size for the first Triple Crown classic needed to be capped. The following year, Churchill Downs limited the field to 20 horses with career earnings as the criteria for qualification. Contrast this with the Preakness and the Belmont Stakes, which both have 14-horse limits. 

As 20-horse fields became more common in the 1980s and onward, Churchill Downs had to change their metric from career earnings to stakes earnings to graded stakes earnings. The points system evolved as a fairer solution to the problem of qualifying for the Derby starting gate. In 2024, the Road to the Kentucky Derby series offered 37 races with points ranging from 1 point for fourth place in an early prep to 100 points for the top tier qualifiers like the Santa Anita Derby, the Wood Memorial, and the Bluegrass Stakes. In addition to the traditional American prep races, Churchill Downs has added both European and Japanese Roads to the Kentucky Derby in an effort to make the race more global. 

Since the introduction of the points system in 2013, the number of races for North American horses has remained relatively the same, with the inaugural season counting 36 races and the 2024 edition with 37. To make the Derby more appealing internationally, Churchill Downs added the Japanese series in 2017 and the European in 2018. The series starts with 13 two-year-old races, ranging from one mile to 1 1/8 miles, and then picks up steam in mid-January with the Lecomte at Fair Grounds and ends with the Lexington at Keeneland in mid-April. The same-year series starts with one-mile races and expands to multiple 1 1/8-mile tests, with the Louisiana Derby clocking in as the longest at 1 3/16 miles. 

With that in mind, how has this shift from graded stakes earnings to points changed how a trainer approaches conditioning their charges for the five-week Triple Crown season? 

Now and Then

Hall of Fame trainer Todd Pletcher is no stranger to the Triple Crown season. Since 2000, he has started 64 horses in the Kentucky Derby with two wins, Super Saver in 2010 and Always Dreaming in 2017, and four Belmont Stakes to his credit, including Rags to Riches, the last filly to win the historic stakes. 

Looking back at his first Derby winner, the path to Louisville with Super Saver “was sort of an interesting one because we really got behind schedule. After the Tampa Bay Derby, he got sick, which ended up pushing us back a week, and we ended up landing on the Arkansas Derby as his final prep, when generally we would have preferred to have four or five weeks from our final prep to the Derby itself. Seemed like the horse had the best month of his life during those three weeks leading up to the Derby.” Getting the WinStar colt enough graded stakes earnings to qualify for the first Triple Crown classic worked out with his placings in the Tampa Bay and Arkansas Derbies in addition to his win in the Grade 2 Kentucky Jockey Club Stakes the previous season. 

In 2017, though, the road to Louisville required collecting enough points to get into the gate. Always Dreaming started his three-year-old season with a win in a maiden special weight and then Pletcher and the colt’s partnership had to make a decision. “The real conversation that we had to have was whether or not we ran in the Fountain of Youth or if we ran in the allowance race the day of the Fountain of Youth. The horse was training exceptionally well, we were very confident that we were on the path to the Derby, and that we had a legitimate derby contender. But in order to make the decision to run in the allowance race, we had to have everyone on board to say that they were willing to roll the dice on one prep race.”

To earn his points, Always Dreaming then had to win the Florida Derby, his lone stakes before the Derby, where “if we didn't finish in the top two, or even if we finished second, it wasn't guaranteed that we would get in based on points,” Pletcher remembered. “Everyone was comfortable with that decision. Everyone wanted to bring him along that way. In this case, we decided to go with that plan and take a shot with one prep race.” The Bodemeister colt won his lone prep and earned 100 points, which guaranteed his place in the Derby starting gate. 

Nick Zito won his two Kentucky Derbies in the 1990s, when graded stakes earnings were the standard for qualification, which meant that juvenile stakes wins counted more than they do today. “Go for Gin won the Remsen as a two-year-old and then came back in the Fountain of Youth and in the Florida Derby, and then he was second in the Wood. So he had already qualified,” he remembered, “Basically, today, with the point system, they're just trying to get as many points as they can because they know there are a lot of horses that are trying to get to the Derby.”

Now, the Hall of Famer sees the Kentucky Derby as “more of an event. I remember Carl Nafzger’s ‘I love you, Mrs. Genter.’ […] And then, of course, Lukas and Baffert keeping this thing up. A lot of people just wanted to be in the Derby after that.” The increasing cachet of having a horse in the Derby has driven more owners to chase the points necessary to be in the Top 20 by the first week of May. 

If a trainer has a Triple Crown contender in the barn, then the point system changes how they map out the horse’s early starts in pursuit of points. “I think what they're doing is, at two they're trying to break the maiden. Then when they get to three, if they haven't broken their maiden at two, [they] go longer […] to try to break the maiden. And after they break the maiden, a lot of them go right into a stakes,” Zito observed. “My theory is they get the calendar out, they see the Jeff Ruby, or they see the Rebel, or they see this race, or that race, or this race, or Gotham, I better go there because I got to get some points.”

The Road to the Kentucky Derby may have influenced some changes to trainers’ strategies for their hopefuls, but it also has mirrored the trend toward racing less often in order to optimize a horse’s performance. The points distribution plays into that strategy, prioritizing the traditional preps in late spring.

Changing Strategies 

All of the races in the points system are a mile or longer, which favors horses stretching out earlier than they may have previously, making shorter races, even stakes, less of a target. “The point system has, I'm not going to say eliminated, but to a large part, greatly decreased trainers running horses in, let's say, the Swale,” Pletcher observed. “Traditionally, a lot of guys would do that and then go to the Fountain of Youth and Florida Derby and kind of take that gradual route of stretching out. And that's just not the way a lot of people are training. They're going to go straight to a long race, and long races have points.”

“Now most of them concentrate on the bigger races. If they don't have the points to begin with, they're going to have to run in a place where they could qualify,” Zito pointed out. “If you run first or second in one of those, chances are you might get in over horses that have accumulated points during the year. So, basically, it'll come down to those last three days, sometimes.”

This emphasis on points rather than earnings has eliminated the chance for early graded stakes winners and stakes-winning sprinters to get into the gate on the first Saturday in May. Even if those early winners did not train on at three, they still had earned a chance to try the Kentucky Derby; similarly, sprinters could set or stalk a fast pace early in the race, setting the stage for closers to make their run for glory in the stretch. The points system instead favors classic distance horses, especially those who can win at eight furlongs or longer early in their three-year-old seasons. With the higher point value preps in late spring, the system minimizes what a horse does in their juvenile season, which means that trainers face a new challenge: how to season a Triple Crown hopeful enough to handle the dynamics of a 20-horse field over ten furlongs while also having them in peak condition for that distance. 

Pletcher also pointed out “the other biggest impact is on fillies. A filly would have to step out and run against colts in a final prep in order to earn enough points,” as Secret Oath did in 2022, but only after she had accrued enough points toward a place in the Kentucky Oaks. Swiss Skydiver also stepped outside of her division to run second in the pandemic-delayed 2020 Bluegrass Stakes, which gave her enough points to qualify for the Derby starting gate. In the end, both fillies deferred that opportunity and ran in the Kentucky Oaks, leaving Devil May Care as the last filly to contest the Derby, finishing 10th in 2010, three years before the points system was instituted. 

Another trend over the five years has been the decreasing number of Derby starters contesting the Preakness. Other than Super Saver and Always Dreaming, Pletcher has “historically skipped the Preakness with a lot of our Derby contenders, and I think that's a good example of trainer management that's evolved over the years. And taking those horses and giving them five weeks in between the Kentucky Derby and the Belmont is part of the reason why we've had a lot of success” in that final Triple Crown classic. 

Zito followed a similar path with his most recent Belmont Stakes winners. “We ran Birdstone, one of the most memorable Belmonts ever, beating Smarty Jones. But he ran in the Derby; he didn't run in the Preakness,” the Hall of Famer observed. With Da’Tara, “he never ran in the Derby, and then he won the Belmont and stopped Big Brown.” His most recent Triple Crown starter, Frammento in 2015, earned his spot in the Kentucky Derby through in-the-money finishes in the Fountain of Youth and the Bluegrass Stakes. After finishing 11th behind American Pharoah, Zito opted to skip the Preakness and instead sent Frammento to the Belmont, where he finished 5th behind the Triple Crown winner. 

The Road to the Kentucky Derby is in its twelfth year, the number of horses going from Louisville to Baltimore remaining steady, with an average of four horses making the trip, until 2023, when only Kentucky Derby winner Mage tried the Preakness Stakes. So far, the decreasing number of horses returning for the Preakness may be attributed more to the trend of spacing races out rather than the effects of pursuing points, a phenomenon which has prompted discussion about expanding the gaps between the Triple Crown classics. As of 2024, any changes to the classic calendar remain an ongoing debate without an immediate resolution. 

The sport has seen two Triple Crown winners since Churchill Downs introduced the Road to the Kentucky Derby points system. Those two champions plus I’ll Have Another and California Chrome were the only horses to win two or more classics in the 2010s; in the century since Sir Barton, that number echoes most decades except the 1920s and the 1950s. So far, the 2020s have not seen any horse win more than one classic, but the question of what is behind trainers’ changing approaches to the Triple Crown season will require more time to answer.   

Graded Stakes Winning Owners - Master Piece & O'Connor - Michael & Jules Iavarone

Article by Bill Heller

Is success more enjoyable the second time around? Michael Iavarone is finding out, on the racetrack, where he has reunited with trainer Rick Dutrow, Jr., and off.

Dutrow is making his own return following a 10-year suspension for drug violations. 

Off the track, Iavarone has rebuilt his own business after being nearly wiped out. “It took me a couple of years,” he said. “I built a bigger business than what I had.”

Iavarone’s love of horseracing traces back to growing up in Bethpage, Long Island, when he and his father fell in love with racing at Roosevelt, then the best harness track in the country with weekend crowds in the 20,000’s. “I loved it so much,” Iavarone said. “I remember it vividly. We’d eat in the Cloud Casino.”

In 1985, Iavarone and his father attended the second Breeders’ Cup at Aqueduct Racetrack, where he saw flawless victories by two incredible turf starts, Pebbles in the Turf and Cozzene in the Mile. “I was 15, and that just hooked me. Pebbles and Cozzene. It was something that always resonated with me. It never left.”

While he built a career as an accomplished investment banker, he began to dabble with Thoroughbreds. On September 28th, 2002, at Belmont Park, Iavarone claimed the New York-bred gelding Toddler for $75,000. He finished fifth in that race.

Iavarone entered him in the $250,000 Empire Classic for New York-breds. Sent off at 49-1, he finished last in the field of 12, beaten 43 ½ lengths. “It was my first race ever,” Iavarone said. “He was dead last. Got beat nearly 50 lengths. I realized you really needed money to do it.”

So he formed International Equine Acquisitions Holding (IEAH) the following year. Based in Garden City, Long Island, the business operated as a hedge fund with horses as the major asset. Iavarone was the co-CEO with Richard Schiavo, who oversaw administration. Major funding was provided by James Tagliaferri, who ran an asset management company, TAG Virgin Islands. Iavarone was responsible for all equine affairs. Initially, IEAH used four trainers, Dutrow, Dominick Schettino, John Terranova and Donald Chatlos Jr.

Although IEAH would campaign several top runners including Benny the Bull, the 2008 Eclipse Award Champion Sprinter, and Grade 1 winners Kip Deville, I Want Revenge, Court Vision and Breeders’ Cup Juvenile Fillies winner Stardom Bound, it will always be linked to Big Brown, a phenomenal horse who won seven of eight starts, including four Grade 1’s in 2008, the Florida Derby, Kentucky Derby, Preakness Stakes and the Haskell Invitational. IEAH was part of a partnership ownership of the son of Boundary out of the Nureyev mare Mien.

Trained for his first start by Pat Reynolds, Big Brown won his maiden debut by 11 ¼ lengths at Saratoga on the grass at odds of 14-1 under Joe Bravo. He was switched to Dutrow’s barn to prepare for his three-year-old season. Hall of Fame jockey Kent Desormeaux would ride Big Brown in all of his seven subsequent starts.

Dutrow called Big Brown “nothing but fun.”

All of Big Brown’s connections had nothing but fun as he won the Florida Derby by 12 ¾ lengths, the Kentucky Derby by 4 ¾ lengths despite breaking from the extreme outside post in the field of 20 and the Preakness Stakes by 5 ¼.

He would go off at 3-10 in the field of nine in the Belmont Stakes and not even finish the final leg of the Triple Crown.

“Coming out of the Preakness, he was fine,” Iavarone said. “He always had problems with his feet. He had glue-on shoes. He developed a real sore spot at the edge of the corona. We decided not to work him. When you don’t do the work, everyone notices. It turned into an abscess. It took away three days from training. As probably the most famous horse, PETA was calling all day long to not race him in the Belmont.”

The morning of the Belmont Stakes turned very weird. “It’s nine o’clock, and I’m in the shower,” Iavarone said. “I got out and went to the door. There are two guys with badges saying they’re the FBI. They show me a letter that had been sent from an unidentified person saying Rick Dutrow and me would be shot in the head if anything goes wrong with Big Brown. I called Rick. He didn’t care. I had two young kids with me. We had two FBI agents with us all day long, everywhere.”

The afternoon was worse than the morning. When Desormeaux walked Big Brown out of the horse tunnel at Belmont Park and onto the track for the post parade, he looked unbelievably upset. Breaking from the rail, Desormeaux pulled him suddenly to the far outside, and, instead of rallying, he kept getting farther away from the leaders. Desormeaux pulled him up and they walked slowly back to be greeted by his connections, all of them wondering what had happened.

“When he pulled up, I went running,” Iavarone said. “The FBI was running behind me. We go back to the barn. He was fine. Sound as a button. We don’t know why Kent pulled him up. He said, `I knew he was going to finish last. Why push him?’”

And the FBI presence? “To this day, we still don’t know about the threat,” Iavarone said.

Dutrow helped Iavarone place the Triple Crown in perspective. “Rick said, `We still won the Kentucky Derby and Preakness,’” Iavarone said. “That day was more difficult for the horse than it was for us, because he didn’t get the recognition he deserved.”

Big Brown bounced back to win the Grade 1 Haskell Invitational by 1 ¾ lengths and the $500,000 Monmouth Turf Stakes by a neck.

Iavarone has much more pleasant memories at Belmont Park thanks to the Cornell Ruffian Equine Hospital right across the street. IEAH built the facility, the only full-service equine hospital on Long Island. “It started with me having a horse needing to ship to New Bolton (in Kennett Square, Pennsylvania) for colicking and we had trouble getting a van,” Iavarone said.

The hospital opened in 2009, closed in 2011 due to financial difficulties and was sold to Cornell University and renamed in 2014. “We built it and it became very complicated,” Iavarone said. “We couldn’t own the facility. We had to lease the facility. It became very hard. So when Cornell came to us about buying it, I saw a chance. I sold it to them. I’m very proud of it.”

IEAH had bigger problems.

Tagliaferri had been investing money on behalf of its clients and receiving kickbacks disguised as consulting fees. In 2014, Tagliaferri was found guilty of investment advisor fraud, securities fraud and wire fraud causing his clients to lose $50 million. Iavarone was never charged with a crime, but felt the effects as IEAH folded.

“It just turned into a disaster,” Iavarone said. “He wiped out about 90 percent of my personal wealth. We liquidated horses and sold the hospital. It sent me in the wrong direction. I was living a great life. I had to go back to my roots.”

When he rebuilt his business, he felt comfortable to return to racing. He became a partner on Next Shares, a Grade 1 stakes winner who bankrolled nearly $1.9 million, and now owns 18 horses including his recent graded stakes winners Master Piece and O’Connor.

And he’s reunited with Dutrow, who scored one of the most meaningful victories in his career when White Abarrio won the 2023 Breeders’ Cup Classic. “Rick and I have been friends forever,” Iavarone said. “Taking 10 years from a guy’s life? At the end of the day, I hope he learned a lesson. He’s a completely changed person now. The suspension humbled him.”

Dutrow said, “I had a ball training for Mike. He’s got a great personality. I will like anybody in the world who sends me horses like he does. He’s got to send me more horses.”

Opinion: Earle Mack - No More Dirt

Earle Mack

In the wake of the tragic deaths of 12 horses at Churchill Downs, the Horseracing Integrity and Safety Authority (HISA) has called for an emergency summit. This presents both a moment of leadership for HISA and an important test for the independent directors of the Churchill Downs Corporation to protect shareholder interests and ensure the survival of the entire horse racing industry. They must step up and meet the moment or step down. This can be achieved by ending dirt racing in America and transitioning to synthetic surfaces.

These heartbreaking events in recent weeks have forced the horse racing industry to confront a harsh reality. On average, two Thoroughbred horses lose their lives every day on U.S. tracks. If we fail to take decisive action, the Triple Crown and horse racing itself may soon be mourned as relics of the past.  Animal rights groups, emboldened by each equine death, are gaining traction in their campaign against horse racing. The calls to ban or severely restrict the sport grow louder with each life lost. We cannot afford to lose this race for the soul and survival of our sport.

Tradition holds great power in our sport, with our most prestigious races historically being run on dirt tracks. However, the stark and troubling statistics demand a shift in thinking. We must abandon old norms and embrace new practices that prioritize the safety and welfare of our noble equine athletes.  The benefits of synthetic tracks are not mere conjecture; they are a proven truth. Their superior safety record and fewer injuries make their adoption not just an option but an ethical imperative.

Skeptics may argue that altering the character of the Triple Crown races would alienate fans. However, declining attendance at Thoroughbred races tells a different story. Fans are turning their backs on a sport they once adored, disheartened by the undeniable fact that their entertainment comes at a deadly price. When other sports have bravely evolved to improve safety and gameplay, we must question why horse racing clings to traditions that increasingly prove deadly.

Certainly, progress has been made. Since 2009, fatal injuries during races have declined by 37.5%. But when we consider that synthetic tracks have been proven to be three times safer than dirt tracks, it becomes glaringly apparent that we have only scratched the surface of what we must achieve. We have solid evidence, compelling data, and a clear path forward. It is time we summon the courage and resolve to embark on this path. Ironically, despite their proven safety record, synthetic tracks are in decline. This is primarily because our marquee Triple Crown events remain steadfastly tied to dirt. The stubborn adherence to tradition in our industry's pinnacle races is a disparity we can no longer afford. Shifting the surface of the Triple Crown to synthetic would be a revolutionary step, igniting an industry-wide transformation and ensuring a safer, fairer field for our equine athletes.

This is where the independent directors of the Churchill Downs Corporation can make a historic difference. Independent directors have played a crucial role in preserving shareholder value and rebuilding consumer trust for some of the world's largest companies.

In 2015, Volkswagen faced a scandal involving emissions test cheating, leading to the resignation of the company's CEO and the appointment of a new board of directors, the majority of whom were independent. The new board took swift action to address the scandal, and Volkswagen is now working to rebuild its reputation.

In 2017, companies such as Uber and The Weinstein Company appointed independent directors to address workplace harassment following a series of scandals in that regard.

In 2018, companies like Equifax and Marriott appointed independent directors to improve their cybersecurity measures after experiencing a series of data breaches.

Today, the challenges facing both the Churchill Downs Corporation and our industry provide an opportunity for its independent directors to lead by proactively and boldly addressing the crisis of equine safety instead of reacting to a growing regulatory and societal movement to ban the sport.

That is why I am calling on the independent directors of the Churchill Downs Corporation, Daniel P. Harrington, MBA, CPA, Ulysses Lee Bridgeman Jr., and Robert L. Fealy, CPA, to get on board today and publicly support this change.

The responsibility lies with horse racing's governing bodies, influential race track directors, and all key stakeholders to rally behind a transition to synthetic tracks. Their public endorsement and commitment to safer racing conditions would signal the beginning of the transformative change our industry desperately needs. But Churchill Downs Corporation must lead the way.

Fortunately, we are not without hope. NYRA's Belmont Track, a vital component of the Triple Crown, is already leading by example, planning to install a synthetic track for its 2024 spring meet. This serves as the spark we need to ignite a safety revolution.

Next year marks the historic 150th anniversary of the Kentucky Derby. This milestone should be more than a nostalgic reflection on the past; it should be a fervent pledge for a safer future. A future where our sport remains a thrilling spectacle but also evolves into a beacon of safety, integrity, and respect for our equine athletes.

The prestigious Triple Crown races–the Kentucky Derby, the Preakness S., and the Belmont S.–now stand on the edge of a daunting, dark abyss. Each life lost serves as a deafening alarm, signaling that change is urgently needed and indeed horse racing as a whole hangs in the balance. We owe it to our equine athletes, our loyal fans, and future generations to ensure that our sport does not crumble into a mournful memory of bygone times.

We stand at the threshold of a monumental shift. Our response to this crisis must be immediate, bold, and unwavering. The clarion call for a race towards a safer future is sounding. Switching surfaces will mean fewer breakdowns and fewer drugs in the sports. Let us answer this call with the courage and determination our horses display every time they take to the track.

This is our defining moment. Let us ensure that the Triple Crown not only continues to sparkle with excitement and glory, but also radiates a renewed commitment to the safety and well-being of our equine companions. The reins of the future of horse racing are in our hands. We must grasp them firmly and steer our sport towards a safer, more responsible era. The heart of horse racing beats in the chest of every horse that runs for us; let us honor them by championing a sport that safeguards their lives.

Roadrunner Racing, Boat Racing and Bill Strauss, Jonathan and Leonard Green (D.J. Stable) and Mark, Stacy and Bob Krembil (Chiefswood Stables)

By Bill Heller

In this issue we profile the owners of three horses who have been major players in the key Triple Crown prep races.

Roadrunner Racing, Boat Racing and Bill Strauss – Hot Rod Charlie

Five football-playing fraternity brothers seeking a way to stay connected after graduating from Brown University in Providence, R.I., did just that by connecting with two veteran Thoroughbred owners in Southern California. Now all of them are having the ride of their lives with their Louisiana Derby winner Hot Rod Charlie.

“It’s astounding,” said Greg Helm, the managing partner of Roadrunner Racing, which owns 50% of Hot Rod Charlie after being convinced by bloodstock agent Dennis O’Neil to take a step away from claiming horses and take a shot with a yearling he liked. “Dennis has a good feel for the personnel groups that would fit together,” Greg said. “Thanks to him, we have a unique ownership.”

The world got a glimpse of this unique group immediately after Hot Rod Charlie won the Louisiana Derby. TVG’s Scott Hazelton was interviewing one of his owners, Bill Strauss, in the winner’s circle. Wildly enthusiastic and raspy after cheering his horse home, Bill fairly shouted, “This is what you get in the game for, to go to Kentucky on the first Saturday of May.” In the background, the brothers were jumping up and down on one another’s body as if they were, well, frat brothers playing boat racing—the beer chugging game they used to name their stable.

“We bring a youthful enthusiasm,” said Patrick O’Neil, the frat brother who is a nephew of Dennis and who bought Hot Rod Charlie as a yearling for $110,000, and his brother Doug, their trainer. 

What do the frat brothers get from their elder partners? “The best thing that happened from this is you get to meet a lot of great new people along the path,” Patrick said. “We are meeting so many amazing people in the world. We are attached to Greg and Bill, who have had very impressive careers. They became mentors to us.”

Working together? “We all have the same mindset about racing, about what’s important to us,” Greg said. “All the decisions that had to be made were unanimous and simple.”

Greg, a 73-year-old retired advertising agency owner, and his wife Glenna formed Roadrunner Racing with five other couples. At their golf club, they watched Hot Rod Charlie’s coming-out party in the 2020 Breeders’ Cup Juvenile, when he led late before finishing second by three-quarters to still unbeaten Essential Quality at 94-1. “They said they could hear the cheering miles away,” he said. “At 94-1, we were pretty pleased.”

His golf club, which had offered a special on its menu that afternoon—the Hot Rod Charlie (a spicy, crispy chicken sandwich)—made it a permanent lunch option. “They have a picture on the menu,” Greg said proudly.

He said of the partnership with Boat Racing, “We’re a pretty lively group ourselves. When you get around the Boat Racing people, it’s hard not to get further energized. We met all of them in New Orleans. That was fantastic. We all sat together, partied together and had lunch together.”

Now he has a horse that deserves a start in a Triple Crown race. “I can almost sleep,” he laughed. “It’s tough to get to sleep.”

Maybe a few beers would help. He could ask any of the brothers—all 28 and in successful careers in California, far removed from those New England winters in college. “I was born and raised in Hawaii,” Patrick said. “Providence was a huge cultural change. I had no boots or a jacket when I went to Brown.”

At Brown, all five brothers played football. Patrick was a cornerback; Eric Armagots a safety; Dan Giovaccini, a linebacker and a senior captain; Reilly Higgins a wide receiver and Alex Quoyeser a tight end. All five joined Theta Delta Chi, where they proved themselves as normal college students by playing boat racing. “Reilly was the best at it,” Patrick said. “Now, after a long and tiring day, there’s nothing wrong with enjoying the great relationship we have over a beer or two.”

Patrick, who admitted watching TVG while he was in class, was drawn into racing by his uncles, especially after Doug won the 2012 Kentucky Derby and Preakness with I’ll Have Another and the 2016 Derby with Nyquist. “We talk every day,” Patrick said. “My dad passed away when I was 22.”

When Patrick took his frat brothers to Santa Anita and Del Mar, they were hooked. “Doug won a couple of races, and he allowed us to go to the winner’s circle,” Patrick said. “They were like, `Wow!’”

Patrick said of their college football days, “We were very, very competitive. We missed it a lot. We got into this game as an excuse to get together. We missed the competition. Horse racing has given that to us.”

Bill, a 62-year-old native of the Bronx who was raised in New Jersey, attended Syracuse University, which allowed him to frequent Vernon Downs, a harness track a half-hour drive away. “I was a trotter guy long before I did Thoroughbreds,” he said. “I’ve always been attracted to the animals. And I love the action. It’s over in two minutes, not three hours. And you can get money back. I loved handicapping. I really loved the puzzle. Am I smart or not?”

He was smart enough to have a successful career, doing high-tech software in California. He did well enough that he helped his brother Jeffrey, now a master chef who has cooked for five Presidents, to pursue his dream. He now runs The Pamplemousse Grille. “It’s one of the highest-rated restaurants in San Diego,” Bill said. “I’m a silent partner. I write the checks. It was a pleasure writing a check so he could chase his dream.”

At the Pamplemousse Grille, Bill met a frequent diner, bloodstock agent Alex Solis II. “He was always there with friends and owners celebrating,” Bill said. “I became friends with him. I approached him about getting my first Thoroughbred, and I was with him for years.”

   Bill and his wife Margie won back-to-back Breeders’ Cup Turf Sprints with Mizdirection in 2012 and 2013 with trainer Mike Puype.

Now he’s chasing victory in a Triple Crown race, with a lot of partners. “It’s an amazing experience,” he said. “In the beginning, you’re alone and get excited. Then you’re with these guys all the way. We discuss what to do—the next race. Patrick recommended the Louisiana Derby. We were completely on board with that because we have so much respect for each other—mutual respect—and we care about each other. Who’d have thought at 62, you’d make lifetime friends?”

    Jonathan and Leonard Green (D.J. Stable) – Helium

Jonathan Green’s priorities crystalized for him at an early age. “I was probably eight or nine years old,” he said. “Our neighbor had a $5,000 claimer. He was racing at Monmouth Park, just minutes from our home. My dad took me. The horse won. I cashed a $5 ticket, ate a hot dog and got to go to the winner’s circle.”

Hooked for life.

Fast forward to college. “I went to Lehigh because Comcast showed Philadelphia Park,” he said. “I’d set up my classes to see the races. I took night classes.”

Now, at the age of 51, he is living his dream as the general manager of his and his father’s D.J. Stable—one of the largest racing and breeding operations in the entire country with more than 100 racing stock, foals and broodmares in five states. “As a family, we’ve really enjoyed it,” Jonathan said. “You have to treat it as a business, but it’s such a thrill to win a big race or sell a big yearling and enjoy it with your family. We’ve won more than 2,400 races and over 150 stakes.”

There is one race they covet winning. They’ve had one starter in the Kentucky Derby—a horse they owned in partnership with former Duke University basketball star Bobby Hurley, Songandaprayer, who set the fastest pace in the Derby’s long history: a half-mile in :44 86 and three-quarters in 1:09.25 before tiring to finish 13th in 2001. But the race they want to win most is the Haskell at Monmouth Park July 17th. “Our Kentucky Derby is the Haskell,” Jonathan said. “We’ve always wanted to run a good horse in the Haskell. We’ve never started a horse in it. The Haskell is a million-dollar race in our backyard…. We’ve done unorthodox things before.”

If Helium were to win a Triple Crown race, that would be tough to resist. That’s what’s classified as a good problem to have. And Lenny and Johnny are good at solving problems. They both succeeded in financing. “My father is 84, and he still works 70-hour weeks and loves every minute of it,” Jonathan said. “My grandfather, Abe, lived to be in his late 90s. He said, `Your mind is a muscle, and you must exercise it daily.’

Lenny is an accountant and CPA who explored the business side of horse racing before getting involved. “He wanted to explore the tax laws to see if there was a benefit for owning horses,” Jonathan said. “He remembered something about the tax codes. He studied it for eight, nine months. Doing that was about as exciting as it sounds.”

Lenny survived and dived in. “He found an industry that he enjoyed that he wanted to be a part of—one that had tax benefits,” Jonathan continued. “He was an athlete. He was a tennis player. He loved competition. In the late 70s, he was a minority owner of the New Jersey Nets.”

The Nets, in the American Basketball Association before it merged with the National Basketball Association, had an outstanding guard named Super John Williamson, who helped the Nets wins two ABA titles. “He was the first actual star I met,” Jonathan said. “He was very gracious. We named a horse Super John.”

Jonathan & Leonard Green with jockey Joel Rosario after Jaywalk wins the 2018 Breeders’ Cup Juvenile Filies

Super John was not a superstar, but an allowance winner who is still racing. The Greens have had many major stakes winners and one champion, Jaywalk, as partners with Cash is King Stable. Jaywalk won the 2018 Gr1 Frizette and Breeders’ Cup Juvenile Filly on the way to the Two-Year-Old Filly Championship. 

In 1989, Jonathan went to his first sale by himself to check out the New Sire Showcase section of the Fasig-Tipton July Sale in Lexington. “I couldn’t take my eyes off a beautiful, steel gray filly across the walking ring,” he said. “She walked with a certain confidence, an aura around her, and had a long stride and peaceful walk. I spent 15 minutes watching her walk, graze and stand in the summer sun. Needless to say, I was in love.”

He got the filly, hip No. 11, a daughter of freshman sire Pancho Villa, for $23,000. “I ran back to the phone bank, made a collect call to my parents and excitedly reported the stunning news of our purchase,” he said. “I was almost 19.”

That filly, Do It With Style, broke a track record at Philadelphia Park in her first start, ran second to Meadow Star in the Comely and won the Gr1 Ashland as a three-year-old.”

Thank goodness for night classes at Lehigh. Actually, Jonathan did benefit from his college education, becoming a certified financial planner. “I started my own company and sold it,” he said. “My primary occupation is managing D.J. Stable.”

He is deeply involved in racing, regularly co-hosting the weekly Thoroughbred Daily News Writers’ Room Podcast, and is on the New York Thoroughbred Horsemen’s Association Board of Directors. He has been the guest lecturer at the University of Louisville Equine Studies Program.

Now Helium, who has made just three career starts, has them thinking about the Triple Crown races and the Haskell. When pinhooker Bo Hunt touted Helium, he told Jonathan he travels so well that his feet don’t hit the ground, that he floats over it. “I looked at the periodic table,” Jonathan said. “I wanted a name of gas to convey that, and helium was the one I picked.”

Helium had won two sprint starts on synthetic at Woodbine in his lone starts at two for trainer Mark Casse, then showed up for the mile-and-an-eighth Gr2 Tampa Bay Derby on March 6th to make both his distance and dirt debut off a 4 ½ month layoff.

Helium won the Tampa Bay Derby impressively. “It was a sensation I’ve only had a couple times,” Jonathan said. “My father called me after the race and said, `The only times I was this excited was when I got married and when your two sisters were born.’” Of course, Lenny could have told him when his three children were born. Jonathan laughed. “My father and I have formed a tremendous friendship over the horses,” Jonathan said.

The team decided not to give Helium another start before the Triple Crown series of races. “We don’t want to wear him out,” Johnathan said. 

Yeah, there’s the Haskell coming up.

 Mark, Stacy and Bob Krembil (Chiefswood Stables) – Weyburn

Weyburn (inside) fends off Crowded Trade to win the 2021 Gotham Stakes at Aqueduct

Some people talk about doing the right thing. The Krembil family, who breeds and races as Chiefswood Stables, has been doing the right thing for humans and horses for decades from their base in Schomberg, Ontario. Along the way, they have emerged as one of Canada’s most powerful stables, winning multiple owner titles at Woodbine and receiving two consecutive Sovereign Awards as Canada’s Outstand Owner in 2018 and 2019. 

Now their colt, Weyburn—named for a small town in Saskatchewan—has emerged as the early favorite for this year’s Queen’s Plate, (Woodbine on Saturday, August 22) following his extremely game victory in the Gr3 Gotham Stakes at Aqueduct March 6th for trainer Jimmy Jerkens.

Before his intended start in Ontario, Weyburn will likely make his next starts in the Gr3 Peter Pan Stakes at Belmont Park on May 8th and then onto the Gr1 Belmont Stakes in early June.

Bob Krembil, the 78-year-old patriarch of the family, founded a mutual-fund company and sold it in 2000. In 2001, he launched the Krembil Foundation. “It focuses on neurosciences,” his 54-year-old son Mark said. “One of my interests is biology. We’re trying to make a difference helping people solve their problems. We’re hoping to help people with Alzheimer’s.” The Foundation also deals with the immune system and arthritis. 

Mark is in charge of the stable’s 125 horses with the help of general manager Rob Landy, a Hall of Fame jockey who rode the stable’s lone Queen’s Plate winner in 2004. “Rob makes the wheel go round,” Mark said. “He does the daily things. My dad really likes the breeding part of it, determining matches. I really enjoy the animal, and I’m competitive. There is nothing like winning a race. Stacy [Mark’s wife] works on after-care, and she follows up on them. My mom, Linda, keeps my dad going. She tolerates all of us, and she loves the animals. Everyone plays a role.” 

The family’s fascination with Thoroughbred racing stretches back to Mark’s grandfather, Jake. “He was an avid fan,” Mark said. “My grandfather would go every day if he could have. I’d go with him and my dad to the Queen’s Plate every year. Later in life, when my father was in a position to enter the business, we started in the mid-90s. Things changed for us when we sold the business, and we started escalating this hobby, and it grew. We have a broodmare farm, a yearling farm and a 7-8ths dirt track. Our goal has been to race at the top of this game.”

They have won at the top of the game, taking their cherished Queen’s Plate with Niigon, who was ridden by Landry in 2004. Niigon’s more than $1.1 million in earnings is Chiefswood Stables’ second-leading earner. Tiz a Slam, who captured the Gr2 Nijinsky Stakes, earned over $1.26 million. Chiefswood Stables now has 344 victories and more than $20.5 million in earnings.

In a February 25, 2020 story in the Canadian Thoroughbred, Bob talked about recreating a new brand for the sport he loves: “We need to build a brand that features honesty, integrity and fair competition so that we can grow the fan base. We need to create an atmosphere where people want to bring their families and groups can be part of the horse racing lifestyle. Part of building that brand is doing a better job showing our love for horses. In a good year, Chiefswood will breed 20 babies, and we will also transition 20 of our racehorses away from the track.”

Mark’s high school sweetheart, Stacy, administers the unique and highly effective Chiefswood Aftercare Program. “I started attending the Queen’s Plate when I was 16 with Mark,” she said. “That’s our Kentucky Derby.”

Asked why having a program transitioning racehorses after their career, she made it sound simple: “They race for our pleasure. We have to take care of them.”

On its website, Chiefswood Stables tells visitors, “Chiefswood Stables is a family owned and operated Thoroughbred racing farm. Our goal is to breed quality Thoroughbred horses to compete in the classic races. It is our belief that the responsibility of care for our horses extends beyond the finish line of their last career races. It is with this belief that we have developed the Chiefswood Aftercare Program (CAP). Our goal is to find lifelong adoptive homes for our horses. We do this by trying to match the right horse with the appropriate adapter.”

What sets the Chiefswood program apart is its follow-up. For the past 10 years, it has had eight to 12 horses adopted annually. “We only had six last year because of the pandemic,” Stacy said. “About five years ago, they finally built me a barn nearby. It works well because the horses can transition slowly. We list them on FaceBook. We follow the horses for a couple of years after their adoption. Then, people voluntarily keep in touch. We get lots of pictures.”

Mark is justifiably proud of his wife’s program. “For two years, the adopted horses can’t be sold,” he said. “They’re happy, and they have a home. Stacy is a fan just like I am.”

The entire Krembil family wants to see the sport they love prosper. “From an outsider’s perspective, the industry appears fragmented with many vested interests,” Bob told Canadian Thoroughbred. “The industry players need to be open minded and work together for the betterment of racing.”

Unraced since December 5th when he won a maiden race, Weyburn fought every step of the way to win the Gotham Stakes under Trevor McCarthy three months later. After the race, Landry said, “We’ve had high hopes for Weyburn all along. We thought he was the real deal, but until they meet those kind of horses you just never know. He ran a fantastic race. He looked like he really dug in hard in the stretch when it counted. He had every reason to give up.”

In return, whether he wins the Queen’s Plate or Belmont Stakes, or never wins another race, Chiefswood won’t give up on him, making sure he—as all of the Chiefswood horses—has a good home, long after his last race.

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The ultimate challenge - Entering the winner’s circle in a Triple Crown race

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This article appeared in North American Trainer - issue 40 (May to July 2016)