BY CYNTHIA MCFARLAND
“It’s not how you start, but how you finish.”
Many people have claimed versions of that popular saying, but it’s the perfect motto for David John and Diane Osterholt becoming Florida breeders.
Now in their early 70s, the couple have clearly found their passion and are pursuing it wholeheartedly.
St. Louis Beginnings
Both David and Diane were born and raised in the suburbs of St. Louis.
“We lived three miles apart and never met until we took a tennis class together in our 30s,” Diane said.
David worked in radiology specializing in cardiology, while Diane worked in the corporate world for a family-owned business, which is a global supplier of manufacturing technology and services.
Growing up, David was fascinated with horses.
“I always wanted to stop and pet them,” he recalled. “Mom and dad finally got tired of me asking about horses and bought me one when I was 12.”
Diane, on the other hand, wasn’t around horses as a child. She started taking lessons and learned to ride after she and David married in 1995.
They bought riding horses, a Missouri Foxtrotter, Blondie, and a Tennessee Walker, Bella, along with a Thoroughbred mare named My Aunt Barbara by Alygo, a son of Alydar. David did some jumping for fun with the Thoroughbred and the Osterholts enjoyed going to jumping competitions as spectators.
That interest in jumping first introduced them to Ocala.
Like many people, the Osterholts vacationed regularly in Florida. While in Clearwater Beach one year, they heard about the HITS hunter-jumper show series in Ocala and drove up to check it out.
“We vacationed in Clearwater about 25 years and took a lot of one-day trips up to Ocala since about 2010,” Diane said.
Florida Bound
When David retired in 2017, he told his wife what he’d been thinking.
“How many more St. Louis winters do you think we can survive? Let’s move to Florida.”
After Diane retired in 2020, they did just that.
“This property became available, and we put an offer in; a week later covid was announced,” Diane said. “We moved here in the midst of the pandemic not knowing anybody but our realtor. When the government said to shelter in place, I knew there was no place I’d rather shelter than our lovely place in Saddlebrook Equestrian Park.”
The Osterholts managed the move themselves, making 12 trips back and forth between St. Louis and Ocala over a period of six months. Their two riding horses happily settled in and the Osterholts rode out the pandemic at their new six-acre farm in Ocala.
How many more St. Louis winters do you think we can survive? Let’s move to Florida. – David Osterholt
Living just up the road from Ocala Breeders’ Sales, when the 2022 OBS Winter Mixed sale rolled around, David decided to stop in.
“I didn’t know anyone there, but I always wanted to try breeding horses,” David said. “Since we had the land, I thought I’d buy one, kind of on a whim. Then I saw another mare I liked and bought her.”
That’s how the Osterholts ended up with two Thoroughbred mares: Glenwood Pines (Mizzen Mast) in foal to Gift Box and Jeekers (Forest Wildcat) in foal to Curlin’s Honor.
Breeding Ventures
Since launching their Thoroughbred operation in 2022, the Osterholts have had eight horses carrying their name as breeder.
As breeders, their first racehorse was Lido Beach, the Florida-bred filly by Curlin’s Honor, out of Jeekers. Lido Beach is a winner of nearly $50,000. The Osterholts consigned her with Bobby Jones Equine at the 2023 OBS October Yearling sale where she sold to Robert Cotran for $15,000.
The Osterholts bred their first stakes winner in Rebel With a Cause, the 2023 Leinster colt out of Glenwood Pines which they named after David’s high school mascot.
The Osterholts sold Rebel With a Cause as a short yearling at the 2024 OBS Winter Mixed sale in the Bobby Jones Equine consignment. The colt brought $10,000 from Gayle Woods.
As 2-year-old, Rebel With a Cause was a $37,000 RNA at 2025 OBS March sale. Now a gelding, Rebel With a Cause has earned $131,012 for owner Tristar Farm LLC and trainer Lauren Robson. He has won three of his five starts to date, including the $104,000 My Frenchman Stakes at Monmouth Park on July 11.
The Osterholts found it thrilling and surreal to watch on television as the horse they bred became a stakes winner.
“To see a horse in the paddock go into the gate and then run successfully when you know that baby was in your backyard and you were able to handle that baby, how satisfying was that?” Diane said. “It’s kind of fulfilling to hear your name mentioned as breeder when a horse wins. We love the bragging rights. While we both had very fulfilling careers, I’ve never been more content than now.”
A fun twist to the story is that Rebel with Cause is literally trained by a neighbor.
“Our neighbor’s wife, Lauren Robson, is his trainer,” David said. “It’s wild to think that his trainer was two doors down from our house when he was a baby.”
The Osterholts didn’t know anything about the Florida Breeder Awards program when they got into the business.
“We learned from other breeders about getting a ‘mailbox check,’” David said. “Now every time we get a ‘mailbox check,’ I say, we’re getting money for hay!”
Rebel With a Cause’s recent stakes win rewarded the Osterholts with a $4,000 Export Incentive check paid by the Florida Thoroughbred Breeders’ and Owners’ Association.
Glenwood Pines and a young Rebel With a Cause (2023) - Diane Osterholt
Expanding the Operation
The Osterholts sold Jeekers, one of their first broodmare purchases, but quickly replaced her—and then some. They currently have eight horses: two riding horses, four Thoroughbred broodmares, one yearling and one weanling.
“We love where we live but needed more grazing land, so we just bought a larger piece of property in Morriston,” David said.
“It’s kind of scary what you can buy online,” said Diane after David discovered online bidding and bought a Charlatan weanling colt at the 2025 Fasig-Tipton November sale. Their plans are to consign him with Richard Kent at the 2026 OBS October Yearling sale.
The Osterholts also bought a young broodmare prospect by Charlatan, Sacred Swagger, at the 2026 Fasig-Tipton January Digital Sale. David became enthusiastic about Charlatan after going to the breeze show at the 2025 OBS March Sale and being impressed by the stallion’s speedy 2-year-olds.
In addition to their original mare, Glenwood Pines, their broodmares include daughters of graded stakes-winners Charlatan, Brethren and Fed Biz.
Their Florida-bred mare Betty, by Brethren, had a 2026 colt by Colonel Liam. They haven’t decided yet whether to sell him as a short yearling in January or wait until next October.
2026 filly by Colonel Liam out of Betty - Diane Osterholt
Looking Ahead
“Our goal is to keep breeding and to buy two more broodmares at the Keeneland November sale this fall,” David said, adding that they plan on attending in person.
Although they’re technically retired, the Osterholts are busier than ever with their growing horse operation. They never had children, but their four-legged kids—canine and equine—have been more than satisfying.
While we have these babies in our care, we give them the best life possible. We just hope and pray the people who buy them do the same and give them the best chance to be successful. – Diane Osterholt
“We use the term ‘retired’ loosely, because we’ve never worked harder than we are now,” David said. “We really enjoy having the babies. It’s peaceful looking out in the field and seeing your horses.”
“We’ve met some really great people of all ages who have given us good advice,” Diane said. “While we have these babies in our care, we give them the best life possible. We just hope and pray the people who buy them do the same and give them the best chance to be successful.”
“We’re doing this late in life and we’re very small, but as you get into it, you strive to do better and better and produce good horses,” David said.
The idea was always to breed, not race, but lately, David and Diane Osterholt have been thinking that might be a possibility in the future. Never say never.
