The sport of horse racing has a rich history, many family legacies, and yes, some nagging issues. So as I see it, a success story involving younger people in horse racing who are not yet household names is one worth telling. In this particular case, the subject of that story is the lead trainer of the racing syndicate I co-founded earlier this year, Claim To Fame Racing Club.
It involves a onetime claimer by the name of Drop A Hint. The trainer is Sam Wilensky, who along with his father Herman, a decades-long veteran trainer himself, turned an eye for value into what horse players call a “life-changing score.” And that makes this latest entry into our Hall of Claim one I’m especially gratified to have seen take place. Because truly, it could not happen to a nicer family.
Here’s the story
The horse was originally purchased back in 2018 for $250,000 by another owner, at the same September yearling sale that her offspring sold at earlier this year. Drop a Hint debuted as a 2-year old at Saratoga that next summer (2019).
After a 5-race run to start her career, in which she hit the board just once, then-trainer Todd Pletcher entered her in a $25,000 claiming race at Gulfstream Park in January of 2020, about a month before the Covid-19 pandemic arrived. That’s where the journey really started.
Sam, operating out of his South Florida home base, from the very same barn his father occupied for decades, dropped a claim for Drop a Hint. Because it seems nothing happens in horse racing without a little bit of luck along the way, he won the claim in a 3-way shake.
From that point on, “Drops of Jupiter” might have been a better description, as this horse became a mega-hit of her own. 15 races over the next 24 months, 10 times in the money (3 wins, 4 seconds, 3 thirds), and over $150,000 in purse earnings. That included a third place finish in the Grade 2 Sands Point Stakes on 10/10/2020, despite going off as a 47-1 longshot.
Wilensky retired Drop A Hint after her final race on 2/12/2022, where she closed out her racing career in style, winning the Minaret Stakes at Tampa Bay Downs. About to turn 5 years old, she was sent to do what mares often do: make babies.
Annually for a few years, for a $75,000 breeding fee, Drop A Hint was paired up for breeding. In this case, while the first two are making their way through the ranks, the third time was the charm. She was bred to Cody’s Wish, an inspiring national-headlines story himself, who won 11 of 16 career races, including multiple Grade 1 contests.
As they say on Seinfeld, yada yada yada…last week that third child of Drop A Hint sold at the Keeneland Yearling sale. Multiple buyers noticed Hip #206, and the bidding became competitive.
When it was done, the yearling sold for $850,000. And while her story is not over, and Sam Wilensky’s training career is just starting to hit its “hockey stick” era, what’s clear is this: Both on track and off, Drop A Hint is an easy call to add to our Hall of Claim.
What’s next for Sam Wilensky’s stable?
Well, here’s Sam this morning. Two days after that magical day at Keeneland, there’s Sam, 700 miles east of Lexington, KY at the brand new Belmont Park. That’s Sam and the rider with one of our Claim To Fame Racing Club barn members, Lure Him In, a horse Sam has played a central role in making a $760,000+ career earner. And he’s still a hard-knocking dude at 9 years old.
As you can see, we’ll be as active at Belmont as the opportunities permit us to be. Along with Gulfstream Park and anywhere else we think our growing stable can compete and win.
As experienced horsemen like Sam and Herman Wilensky know, you work your a%$ off, you keep at it, and you treat people with the utmost respect. Whether they are owners, jockeys, grooms, farriors or strangers. And with perserverence, time, learning more every single day, and putting the horse FIRST, you just might end up telling your story to someone like another next-gen industry leader, Gabby Gaudet. Here’s her interview with Sam right after that life-altering Keeneland moment.
Coming Up Next
We’ll have a lot more on Claim To Fame Racing Club’s story in the coming days, weeks and months. We are all about expanding the reach of thoroughbred racing, to include a wide range of fans and owners of all ages, backgrounds and interests.
This sport unites us. And we’re charting our own course in a way we hope shines a most positive, transparent and inclusive light on racehorse ownership, and the pure enjoyment we all get from it.



