Illinois champ bringing Bycrofts plenty to celebrate
Given Cash Money Twenty’s namesake, the 4-year-old gelding had a lot to live up to, but he’s far surpassed all his connections’ hopes and taken them on the ride of a lifetime.
Named in honor of their late nephew, Ted and Sherri Bycroft’s spontaneous 2023 yearling purchase has proved to be a bright spot during a bleak time for the family.
Cash Money Twenty, or simply “Cash” as he’s known in the barn, was purchased at the 2023 Heartland Standardbred Sale in Cannon Falls, Minn. Ted and Sherri Bycroft had gone to the sale seeking a Minnesota-bred, but they had yet to purchase anything as the sale progressed into its later stages. Sherri nudged her husband, encouraging Ted to bid on the strapping Illinois-bred yearling colt in the sale ring, originally named Itjustcomesnatural. Ted complied, and the hammer fell. Ted recalls the dam, Hostess Lisa, as a gritty mare with a fast mark, and he had jotted down “nice looking” on the colt’s sale page. Getting him at the price of just $4,000, the Bycrofts were thrilled with what they considered a good deal. They had no idea at the time, though, just how good of a deal it would turn out to be.
Earlier that summer, the couple unexpectedly lost their 36-year-old nephew, semi-professional softball player Cassius Hart.
Ted described his nephew as easy-going and fun-loving:
“He never met a stranger and was a friend to everyone.”
Given his talent, proclivity for coming through in the clutch when it really counted on the field, and the fact that his jersey number was 20, Hart had earned the moniker “Cash Money Twenty.”
Considering Hart’s natural ability, the family’s devastating recent loss, and their new horse named Itjustcomesnatural, changing his name to Cash Money Twenty seemed almost meant to be. In another turn of serendipity, both Hart and his namesake had been “born and bred” in Illinois. However special this gesture was, Sherri admits it added some pressure because they so wanted this young horse to do well and make everyone proud.
Bringing things full circle, Hart’s dad, Terry, was the one responsible for getting Ted involved in harness racing. Terry took a young Ted to Quad City Downs to watch the races. That’s all it took: Ted was hooked and went on to train horses in the late 1980s and early ‘90s, but he eventually decided to give up the often unpredictable life of racing to start a family and settle down. By the time he married Sherri in 2017, Ted wanted to get back into racing.
In 2019, Ted’s dad passed away. And, after the Bycrofts inherited some money, Sherri said they were ready to “see if they could do something [in racing].” They purchased their first yearling and named her in honor of Ted’s mom. She didn’t race until she was 4 years old. More racehorses followed, but none of notable distinction.
By 2023, after buying Cash Money Twenty on a whim, the Bycrofts were in the midst of a trying time when it came to their relatively recent foray back into harness racing. In July 2024, they were down to a barn of just one, their Illinois-bred pacing colt. Sherri admitted, “It was a make-or-break situation for us by that point.”
The next hurdle was finding a trainer for the equine Cash Money Twenty.
The Bycrofts’ regular Minnesota trainer, Brett Ballinger, agreed to take him until the time came to send him to Illinois — if that time came. Though Ballinger was pretty tight-lipped about the colt as he trained down, Ted believes his trainer knew he had something special but didn’t want to prematurely get his owners’ or his own hopes up.
Ballinger later admitted, “He was the best horse I’ve broke since Fox Valley Gemini,” a 67-time winner and two-time Illinois Horse of the Year who amassed $788,636 in purses, won Illinois Night of Champions events each year from 2017-22, and is a 2026 inductee into the Illinois Harness Racing Hall of Fame.
Sherri added, “Brett just kept saying, ‘I think he’s going to be alright.’ When we qualified him at Running Aces, he looked great. That’s when we started feeling some real nerves and excitement about him.”
Following that first qualifier, Cash Money Twenty won three races in a row at Running Aces with James Kennedy in the bike. The $4,000 purchase proved himself enough to at least try to compete in Illinois stakes races. He did far more than just compete. Cash Money Twenty was moved to the Mike Brink barn and went on to win 11 of his 12 starts his freshman season. When all was said and done at the end of his 2-year-old year, the Stevensville colt had taken a mark of 1:50 at Springfield and bankrolled $206,253. He was deservedly voted Illinois’ 2024 Horse of the Year.
During his 3-year-old campaign, Cash Money Twenty increased his lifetime earnings to $324,450 and visited the winner’s circle nine more times, including after his season-concluding 1:51.2 score in the $110,000 Robert F. Carey Jr. Memorial at Hawthorne. Through 26 lifetime starts, he has finished first or second in all but one, and his continued dominance as a sophomore earned him a second Horse of the Year title in the Prairie State.
“It is super exciting to see any individual — human or animal — succeed when they have so much talent,” said Ted. “Too often these days, so much talent is wasted for a lack of effort, desire or drive. We have had so much fun — and anxiety — throughout this journey with Cash.”
As far as what’s in store for the future? The Bycrofts are looking forward to racing him in Minnesota at their home track this year. Ted explained that Cash Money Twenty may go out east to race eventually, but “we are in this for the love of the sport and enjoy doing it ourselves — together.”
And he’s not just saying that because it sounds good.
Every morning, Ted and Sherri can be found at the track in the Ballinger barn, working around and jogging their horses. They race their horses at night. They’re as involved as any owners out there, but they never take it for granted.
“Cash has provided us with an opportunity that many horsemen work their entire lives and never attain,” said Ted. “We realize just how fortunate we have been with our success and we are so thankful to all the friends and horsemen and women that have helped us get to this point.”
“We are so grateful to Mike Brink and Lori Searle for taking such good care of him in Illinois, and to Casey Leonard, who managed him so well on the track,” added Sherri. “He can be a challenge on race day, and all three of them saw that he was extremely talented but needed some help keeping it together to get through these last two seasons. We are super excited to get him back in Brett’s barn in 2026 and continue working on developing him into a seasoned racehorse. It will make my heart happy to walk into that barn and see his beautiful face. To me, he is the most special horse that we have owned, and I can’t wait to see what he does from here!”
Both the human and equine Cash Money Twenty are still bringing family members together and strengthening the relationships between them. Ted and Sherri visit Hart’s mom in Kansas City after big wins to celebrate together.
“She has always been supportive, but never really taken an interest in our horses until Cash came along,” said Ted. “Now she watches his races when she can and attended the Illinois Harness Horsemen Association’s 2024 awards banquet with the rest of Cassius’ family to help us accept our Horse of the Year award.”
The family is planning on reuniting again at this year’s Illinois awards banquet to honor both Cash Money Twenty and the memory of his namesake. This spontaneous $4,000 purchase has proved a light in more than just the lives of the Bycrofts following the tragic loss of their nephew.
“I feel like Cash has given us something to celebrate in honor of his namesake, and a positive thing to keep the extended family communicating and engaged as he continues his racing journey,” explained Sherri.
For the Bycrofts, everything about this journey has been quintessentially bittersweet. While they wish they’d never had a reason to name a horse in honor of a young family member gone too soon, Cash Money Twenty has brought more joy and moments of celebration than their family could’ve imagined.
“From the first qualifier to his 3-year-old championship race, he has kept us on the edge of our seats,” Ted concluded. “But through it all, we knew Cash had his guardian angel watching over us.”
This story appears in the March 2026 issue of Hoof Beats, the official magazine of the USTA. To learn more, or to become a subscriber to harness racing’s premier monthly publication, click here.