Following in his father’s stirrups: One jockey’s path to a history-making start at the Kentucky Derby

By Dana O’Neil, CNN

Louisville, Kentucky (CNN) — In 2004, an old fraternity brother gave Ken McPeek a call, looking for a favor.

Bruce Casella went to Eastern Kentucky, a few minutes’ ride from McPeek’s University of Kentucky but they both were Sigma Alpha Epsilon brothers with a shared affinity for horse racing.

McPeek came by his naturally. His dad, Ron, owned and raced several thoroughbreds from their Lexington home base. Casella, a Philly kid, found his during his four years of college. When they weren’t playing pickup or trying to dunk on each other’s heads on six-foot rims, they’d head to nearby Keeneland.

By 2004, McPeek had ditched his business administration degree and a shot to be a stockbroker to go all in as a trainer, his highlight coming in 2002 when his horse, 70-1 longshot Sarava, won the Belmont and ruined War Emblem’s shot at a Triple Crown. Casella, meantime, had parlayed his love for horses into a TV career, moving from a Kentucky affiliate to ESPN and finally back home to Philadelphia, where he created and produced “Let’s Go Racing” out of what’s now called Parx Racetrack.

As a mainstay at the Philly track, Casella had the inside scoop on a three-year-old horse that had blazed through Kentucky Derby prep races, winning the Southwest Stakes, Rebel Stakes and Arkansas Derby in the three months leading up to the first Saturday in May. Casella thought it would be helpful if the horse’s jockey got acquainted with Churchill Downs, so he called McPeek to ask for an assist.

McPeek let Stewart Elliott gallop and work a bunch of his horses, making sure the jockey got on the track every day to familiarize himself with its famous surface and idiosyncrasies.

On May 1 of that year, Elliott rode Smarty Jones to a two-and-three-quarters length win in the 130th running of the Kentucky Derby.

Twenty-two years and one day later, Elliott’s son, Chris, will ride Right to Party in the 152nd Kentucky Derby, making the Elliotts a rare (less than 10) father-son jockey duo to earn a Derby ride in the race’s history. The horse’s trainer? Ken McPeek.

A family legacy

Philadelphia magazine recently ranked the 25 most “Philly” athletes of all time, considering not just wins, losses and stats but how much the athlete personified and resonated with the essence of the city. Smarty Jones came in 15th.

Stabled in the very unremarkable Philadelphia Park and owned by a local car dealer, Smarty was the perfect blue-collar horse with an equally perfect blue-collar name to suit a city that is slightly less than Derby refined. He also came along at just the right time; the city so starved for a winner of any kind that it hopped on the horse’s trailer-bandwagon.

By May 2004, the Philadelphia pro sports championship drought stretched for 21 years and not two months earlier, Saint Joseph’s, a quintessential Philly underdog, lost in the Elite Eight after rising to No. 1 in the nation. Started after the Kentucky Derby win, Smarty fever continued in Baltimore, where the horse won the Preakness by a record 11-and-a-half lengths. As the horse’s trailer made its way up Interstate 95 to try and win the Belmont and break the Triple Crown hex, people in cars honked their horns while well-wishers hung over overpasses to cheer him on.

Chris Elliott experienced none of that. He was born in 2006, two years after his father’s career highlight. As he grew up, he certainly wasn’t ignorant of his father’s success. His childhood home in Lambertville, New Jersey – a small town tucked on the Delaware River known more for its antiques and annual Shad Festival than its horses – was filled with Smarty trinkets and trophies.

It also sits only a short 30-or-40-minute ride to Parx and each year, Chris would join his family at the annual Smarty Jones Stakes, the race the track hosts in honor of its most famous son.

Chris liked horses enough. He rode a pony named Vivid on the farm, but he didn’t necessarily see himself following in his father’s footsteps. Instead, he took karate lessons and for a time, fancied himself a basketball star (he remains a hoops fan; his team is the Milwaukee Bucks).

Chris joined multiple travel teams and though he could play, genetics eventually caught up with him. Stewart is 5’4”, tall for a jockey but about a foot shy for hoops. Chris’ mother, Lilibeth, is also the granddaughter and daughter of jockeys, so he wasn’t finding added inches there, either.

The family left New Jersey in 2016, the weather making it impossible to sustain a long-time riding career for Stewart. He rode for John Servis, Smarty’s trainer, at Turfway Park in Kentucky and spent time in California, working for Mark Casse. It was there, at the beautiful confines of Del Mar, not from San Diego, that Chris finally caught the riding bug.

“I wasn’t going to steer him to it or away from it,’’ Stewart told CNN Sports. “I know both sides of it and I’d just as soon he not do it. If he didn’t have the talent, I would have told him, but he did.’’

Chris started watching races more closely, both live and taped versions. Unlike a lot of teenagers, Chris also sought and heeded his father’s advice. To this day, father and son will break down Chris’ rides post-race.

“He tells me when I do something right or wrong,’’ Chris told CNN Sports. “And he tells me straight.’’

‘He really is beyond his years’

In 1981, 16-year-old Stewart Elliott won the racing title at Atlantic City Race Course, following in the footsteps of his own father, Dennis, who carted the Elliott family as far away as Hong Kong to chase a career as a jockey.

By the time he entered the starting gate for the Kentucky Derby 23 years later, Stewart was 39 years old, road-tested by injury and four years sober after coming to grips with an alcohol addiction. He’d made tens of thousands of starts, barely nudging the needle on notoriety.

Chris Elliott turned 20 last week. He started his first race just two years ago and now will start in the Kentucky Derby, the youngest jockey to ride in the sport’s biggest event since 2007.

“It’s unbelievable that it’s happened so quick,’’ Stewart says of his son. “But he has a great attitude. He learns quick. He listens. He takes advice. He is really beyond his years.’’

Like his father, Chris got a little lucky with his Derby mount.

In November 2003, trainer John Servis asked Stewart to ride Smarty Jones at Parx at the same time another trainer, Ned Allard, offered him a mount with a horse named Deputy Rummy. Deputy Rummy started 10 races and won $60,000 in prize money. Last year, Smarty Jones was named to the National Museum of Racing and Hall of Fame.

Chris was more right place, right time than right horse. In 2024, McPeek pulled off a rare double, winning both the Kentucky Oaks with Thorpedo Anna and the Derby with Mystik Dan. As the sport goes, success bred opportunity and McPeek’s barn has grown with more horses at tracks stretched across the country.

Chris races often out of Aqueduct, where Right to Party was stabled and, in November of last year, steered the horse from near the back of the pack to a third-place finish in a six-furlong race.

“I told Kenny afterward, as soon as he can get to the longer distances, he’s gonna win,’’ Chris says.

A little less than a month later, Right to Party followed his same route, starting far back before roaring back but now with a mile of ground to cover, he had more room to stretch his legs and finish first.

A third-place finish at the Gotham Stakes put him on the Derby trail and a second-place finish at the Wood Memorial gave the horse enough points to claim a spot in the starting gates on the first Saturday of May.

But nothing is guaranteed in horse racing, particularly a 20-year-old jockey’s ride on a Derby contender.

With his Beastie Boys’ analogous name, Right to Party might become popular with bettors but he’s not likely to be an actual Derby favorite. Still, Mystik Dan went off at 18-1and won the Derby. McPeek, as well as anyone, knows that anything can happen.

Trainers change jockeys all the time and McPeek would have been within his rights to swap Chris Elliott out for a more seasoned jockey – such as Brian Hernandez, who rode both Mystik Dan and Thorpedo Anna in 2024.

Instead, the day after the Wood Memorial, as Chris was finishing some morning work, McPeek called and said he’d be riding in the Derby.

“You can see it in his eyes; he wants to be important. He wants the big races,’’ McPeek said. “He’s coachable. To me, life is about opportunity. I wish someone had given me a chance when I was younger. He knows this horse and to me, it wasn’t even a decision to make. I was going to stick with the guy who got us here.’’

‘Run the race’

In 2002, McPeek thought for sure he had a contender in Harlan’s Holiday, who had won both the Fountain of Youth and Florida Derby prior to the Derby.

Instead, the horse got stuck behind traffic early and was never really a threat. He finished seventh.

As Stewart acclimated to the Churchill track in 2004, the trainer offered the jockey some unsolicited advice he learned the hard way with Harlan’s Holiday.

“When you leave the gate, let him run to the first turn,’’ McPeek told Stewart. “If he has natural speed, allow him to leave the gate and get into position. Don’t let yourself fall back and have to fight your way through.’’

In replays of the Derby – replays that Chris estimates he’s watched more than 1,000 times – Smarty Jones, starting from the outside in post position 15, is nearly sandwiched between two horses on either side before the first turn. At the last second – “as the sea was closing,’’ McPeek says – Stewart guided the horse into the clear out of the slimmest of spaces and eventually on to the win.

“Harlan’s Holiday missed that but Stewart got it,’’ McPeek says. “He shoved that horse through that hole.’’

Last week, Stewart was at his home in Auburn, Kentucky, where he and Lilibeth now live. Later, he would fetch Chris from the airport, the son coming home for a little birthday celebration before heading to Churchill.

The two have talked regularly about the Derby. Chris has only been to the big race once, and he was an infant, so there are zero memories. Stewart has told him about the emotion, the pomp and circumstance, the crowd size and how, even if you want to stay calm, when My Old Kentucky Home is cued up on the loudspeakers, it’s impossible to not be affected.

“I told him it doesn’t matter if it’s a $5 million race or $5,000; we’re jockeys and our job is the same,’’ Stewart says. “When the gates open, your job is to get the horse where it’s supposed to be. In this case, with 20 horses, it is a little different. You have to get away clean. I told him, you have to get him into that first turn. Let him go to that first turn and then run the race.’’

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