If you’ve been around Wall Street or the investment world for five minutes, you’ve heard the old saying: there’s no such thing as a free lunch. Very often, things come with a cost, a catch, or a hidden fee.

In horse racing, that happens as well. But when you look at how racetracks compete for horses across the national map, you run into one of the rarest setups in sports: a track willing to hand you extra prize money and a cash bonus just for pulling your horse trailer into their barn area, and racing during their meet.

They call it a Ship & Win program, and it’s about as close to a “free lunch” as a racehorse partnership is ever going to find.

Why Racetracks Hand Out “Free Money”

To understand why a racetrack would pay you just to show up, you have to understand how track economics work. A racetrack isn’t just a sporting venue; it’s a wagering marketplace. The lifeblood of that marketplace is “field size.” That’s the number of horses running in each race.

Bettors dislike small fields with four or five horses because the payouts are tiny. But when a race has nine, ten, or twelve horses, the betting pools explode. More horses equal more betting handle, which generates higher revenues for the track. It also appeals to those (like me) who are very light bettors, but enjoy the challenge of analyzing and winning.

So, to attract horses from other states and fill up their daily race cards, major tracks created Ship & Win incentives.

The mechanics are simple:

• Guaranteed Starter Bonuses: A flat cash check paid to the owner just for making an out-of-state horse’s first start at the meet.

• Purse Enhancements: A percentage boost added on top of whatever prize money the horse earns in its races.

Del Mar in Southern California pioneered the modern Ship & Win format back in 2011 to revive its summer field sizes, and it set off a trend across the country. Today, you see similar starter bonuses and shipping incentives popping up at tracks like Saratoga and the new Belmont Park in New York, Oaklawn Park in Arkansas, and others. Particularly for meets like Del Mar, which is primarily a 2-month season from mid-July through Labor Day, providing some incentive helps all around.

Evaluating the “Free Lunch”

For a syndicate like ours (Claim To Fame Racing Club), looking at the national map through a Ship & Win lens is just smart business. And one of many ways in which we are trying to clearly differentiate our approach to the racehorse ownership business.

• The Upside: It boosts the earnings potential of a standard race without requiring your horse to step up into harder competition. The guaranteed starter bonus helps offset the cost of cross-country transport, while the extra purse percentage gives your partners a much higher return when your horse runs well.

• The Catch: It’s only a “free lunch” if the horse handles the trip. Shipping horses across state lines involves travel stress, climate adjustments, and new track surfaces. If a horse doesn’t settle in or dislikes the local dirt, those financial bonuses don’t mean much. That’s what we rely on our expert horsemen, Sam Wilensky and Victor Collazo, to weigh in making those decisions for us.

When we first raised “friends and family” capital for Claim To Fame Racing Club earlier this year, we felt compelled to devote a full page to it in our “pitch deck.” Here’s what that looked like.

As it turned out, the opportunities were even more diverse than that simple 3-city outline above. That picture at the top of this article, the one showing a multi-city trip that my wife noted looks a lot like the state of Kentucky (though that state was not one of the stops)? That is the path that one of our horses, the veteran runner Lure Him In, has taken since July.

He shipped to Del Mar and ran there and when that season ended, we shipped him to NY with plans to run in the Northeast at least once. But the races we targeted for him did not fill up, so our horsemen adjusted with the flow, so to speak. He ran at Laurel, did very well, and now joins the rest of our crew at our Gulfstream Park home base for the winter season. Unless, of course, an ideal race pops up for him elsewhere. That’s “Geographic Arbitrage!”

Keep in mind that many horses could not be “road warriors.” But “Big Lu,” who I featured in my last post here, is no ordinary horse. He’s a 9-year old inspiration. In the same way that my brother has logged so many airline miles during his career as a healthcare executive, I know it is more than I could handle.

But apparently, based on attitude and performance, some horses thrive on it. As the horseman always tell me, horses are as different as people. And frankly, while the horse cannot “tell” us what they think of the travel/no travel paradigm, they do in other ways.

Which is why horse care is the priority. No matter how much money might be on the line in some other state or city.

When we evaluated our own stable’s needs, cooler weather and strong racing setups, plus taking advantage of a circuit like Del Mar made complete sense for our runners. Sam has been racing there for years, and knows the territory. The ocean breezes provided a fantastic environment for the horses, and the Ship & Win economics made the trip worthwhile.

And, it doesn’t take a Ship & Win incentive for us to ship a horse to run somewhere else. Remember, South Florida, where we are most of the year, is at the southeast tip of the US. You can drive for 6-10 hours depending on direction, and STILL be in Florida! And Gulfstream and Tampa Bay Downs are the only two tracks in the state. Tampa runs about half the year, and GP all year round. So getting on the road is part of how we seek to gain a long-term edge.

To that end, here’s a segment of a partners update note I sent out several months ago, when we were looking at potentially running one of our horses at Penn National.

Race Day On The Road

Because our partner group is spread out across Florida, Pennsylvania, New York, and beyond, shipping out West gave birth to what we call “California Streaming.”

When race day arrives in San Diego, everyone tunes in remotely. We pull up live video broadcasts on laptops and phones, fire off comments via text, and watch the odds shift right up until post time. When the starting gate opens, the adrenaline is identical whether you’re sitting in a grandstand box at the finish line or watching on a tablet from your kitchen counter 3,000 miles away. I’ve already (happily) responded to last-minute requests for “where can I watch the race live?”

We started this initial group as a small, closed partnership of friends and family to test our operational model and get our horses to the track. We aren’t taking on new investors right now.

Down the road, our goal is to open future partnership groups that bring more fans into the fold. Giving people a clear, transparent look at racehorse ownership without needing a fortune.

For now, the best way to experience what we’re doing is simple: follow along right here on the blog. And tell your friends and family that you think may be interested. It costs zero, and eventually we’ll be running events like “Owner for a Day” meetups at the track. Regardless of your interest level, we invite you to enjoy the ride with us.

Hey, I think I just told you the other free lunch in horse racing.

The gates are open, and we’re just getting started!

That picture is a second place photo from a random lower-end claiming race at the magnificent Del Mar race course, where Claim To Fame Racing Club lead trainer Sam Wilensky typically races in the summer. Sam, like his father for decades before him, has his primary operation out of Gulfstream Park. But between the higher summer purses in places like Del Mar and Saratoga, if you have the horses to run competitively there, it saves you and them some of the wear and tear of the South Florida summer.

That photo is likely not much of a memory for horse racing fans. But to those of us who navigated through a few months of a mystery injury, for a horse that seemed to have lost his desire to race, finishing third by a nose felt like winning on Breeder’s Cup day!

And, as I noted in that segment of a post to our partners later that day, being nosed out for second place meant $3,000 less purse winnings for that particular race. So if you’re looking for examples of the embedded and constant win-lose scenarios in this sport, there you have it! It prompted me to recall one of the great TV comedies I enjoyed growing up during the 1970s, Get Smart.

Swaggish: Can’t he just TELL US what’s going on?

When an athletic runner puts together a few of disappointing races in a row, you have to play detective. That’s what Sam did with Swaggish. After we claimed him, he had a couple of races where he broke cleanly from the gate, got into a perfect winning position near the lead... and then completely ran out of gas when asked to finish. He wasn’t getting beaten by faster horses. he was simply stalling out.

Sam went to work as the horseman on the ground. A thorough veterinary check revealed nothing that would explain that on-track performance. Like human pro atheletes, there’s always some minor issues with every horse. That’s why the training regimen for all horses includes things water therapy and detailed grooming on a regular basis. So nothing from the vet that would explain the sudden change in form for Swaggish. We had a healthy horse.

But in this case, all of the usual remedies that would typically cause a racehorse to jump back into form just were not working. It was maddening.

I took this picture when visiting the barn last spring, in the midst of this slump for our boy. Sam points to Swaggish in his stall and says, “take a look, I just fed him a little while ago, I’ll bet he’s already finished all his food.” If a horse is eating well, that’s a good sign.

Sure enough, I pointed the camera down at his bowl…”drain-O!” Sam then reminds me that from day one, this horse has done “everything right” in terms of training process.

So, what’s with him? This is not the horse we thought we claimed in Tampa last April, with 5 career wins and a body that looks poised to win some more.

There are so many variables in this game. And again, the horse won’t tell you. So, what do you do?

At the same time, we looked at his past racing records. Across his career, Swaggish consistently ran his fastest times in cool spring and late-fall weather at northern tracks like Woodbine in Canada or Churchill Downs in Kentucky. But in the boiling, humid summer heat of South Florida, his performance dropped off significantly.

That’s when Victor and Sam made the decision that turned it around. They dropped Swaggish to a low-level claiming race, where he ran like he used to. It was a shorter distance as well, which made a lot of sense even if it hadn’t worked, given the aforementioned issues.

Then, 4 weeks later we ran him back, again at Del Mar in San Diego, in a higher level claiming race than the previous one. Another third place finish!

Here’s what Swaggish told us, in looking back to his tough spring

NOTHING. Because horses can’t talk. And sometimes, they behave normally, 24/7. Then on race day, whatever issue they have comes out, in front of a crowd.

Swaggish is back at Gulfstream, likely hoping the weather cools off. But he’s back to form. And for a new stable, we are frankly grateful to have gone through this with him. Because this game is, if nothing else, a never-ending series of highs and lows.

“Wait for the shake.”

One of the things you learn as you go from “it would be fun to own claiming horses” to “what do you mean we didn’t get that horse?” is that claiming is really unlike any other part of a sport one experiences.

You see, any licensed owner can place a claim slip in the claim box before a claiming race at any racetrack. Once the race starts, if there’s at least one owner who agreed to purchase that horse at the predetermined claiming price for that race, they are walking away a few minutes later with that horse. With a red tag around their neck, indicating they have been claimed out of the race they just ran.

The owner who entered the horse in that race wins any purse money from that race. And they’ll get paid quickly for the sale of that horse. But just because you put in a claim, doesn’t mean you’ll get the horse. Even if you are the only one vying for the horse, you might not take them back to your barn.

After each race, a claimed horse is checked by the track veterinarian to make sure that the new owner is getting a healthy claiming horse. Such “voided” claims do not happen often. What is more likely these days, as claiming horses becomes more popular and thus more competitive, is the contest known as “the shake.”

I’ll conclude this post with a quick recap of our shake experience so far with Claim To Fame Racing Club. Sam and Victor, my partners, have done this for years. But for those of us with just a few years under our belts, or our club members who own claimers for the first time, this is a real eye-opener.

Speaking of that, while it is rude, crude and now part of ancient movie comedy history, I’ll share it anyway. This scene from Mel Brooks’ iconic 1981 History Of The World, Part 1 is one I just cannot get out of my brain each time Sam and Victor tell me “we are dropping a claim on horse XYZ in race X at Y track on this date.”

When you win a 13-way shake as we did for Swaggish at Tampa Bay Downs in the early going, as I described in an earlier post, the temptation is to think “we’re gonna win a lot more of these, and soon!” But as one club member keeps reminding us, for every one of those we win, we might lose 12 straight.

And that’s about how it went for us. A dry spell. Not unexpected, but when you find a horse and get yourself pumped up, with a forward-looking plan already being devised if you win the claim, finding out there is a shake is a minor source of pins and needles. Then when you lose them, over and over, and come to realize it is all part of the game, you can finally relax.

That took some of us about 3 months! But now, “waiting for the shake” is much more matter of fact. Over the weeks that followed the April longshot claim win for Swaggish, Sam (our head trainer) and Victor (our operating partner and CPA) scoured upcoming race schedules, analyzed past performances, and identified several runners that fit our budget and athletic criteria. We submitted claim slips on targeted horses, only to get knocked out in draw after draw.

That is the raw, unvarnished reality of building a stable through claiming races. You can do all the research in the world, spot a horse with massive potential, crunch the numbers, and walk away empty-handed because a numbered pill rolled the wrong way in a bottle. It takes patience, emotional discipline, and a willingness to keep showing up.

What if I don’t want to wait for the shake?!

Hey, claiming is how we’re starting Claim To Fame Racing Club. But there are many other ways to acquire a racehorse. Auctions, private sales, and even breeding your own. We’ll discuss all of that here in the coming weeks and months.

In fact, other than Swaggish, we have currently purchased 3 other horses. One was acquired through a claiming race with no shake. No one else had any interest in him. That’s another upcoming post topic.

Yet another was acquired through a private sale. Again, I’ll reserve that story for its own post. It deserves one.

And, earlier this month, after losing shake after shake at racing offices in multiple states, we finally had those racing lords bestow upon us…a win in a 5-way shake! Some would say we got lucky. In our minds, after months of adventure in the claiming game, WE WERE DUE!

That’s a picture of Swaggish, happy as ever, in his barn stall earlier this month. But the process involved in how we claimed him out of a spring race at Tampa Bay Downs, as well as the ups and downs since that time, is a story. So here’s that story.

The Claim Game

To understand how middle-market racehorse ownership works, you have to understand the claiming box. Over 70% of all races in North America are claiming races, meaning every horse in the field has a literal price tag. If you want the horse, your trainer drops a written claim slip into a locked box before the gates open. The second the gates open, if at least one owner has entered a claim slip for a horse, barring a “voided claim,” the horse belongs to that new owner. No matter how the horse does in that race.

The previous owner earns the money from the horse’s finish in that claiming race, but the horse leaves the track wearing a red “claim tag.” And the new trainer escorts their new acquisition to their new barn.

This is what makes the claiming game the most liquid aspect of race horse ownership. And why claiming syndicates tend to attract people who motivation includes being able to see their horses run more frequently.

As my friend Howie Heiberger, Managing Partner of In Front Racing Stables, who helped introduce me to the claiming game told me, “for the horse racing fans who want lots of action, claiming gives them that.” So true!

How Swaggish Ended Up Wearing Our Silks

When our syndicate set out to acquire our first runner, we targeted a 5-year-old named Swaggish. We liked the fact that he has competed well with stronger horses than the $20,000 claiming level he was racing at that April day at Tampa Bay Downs. We also liked his speed figures and his physical build. That his name was pretty cool was not a factor in the decision, but it certainly was a positive point!

But we weren’t the only ones.

When the race ended, 13 different trainers had dropped claim slips on the same horse. In racing, when multiple people claim the same runner, it comes down to a “shake.”

The track stewards put 13 numbered pills into a plastic bottle, shake it up, and pull one out. Whoever’s number pops out walks away with the horse.

Against a 13-to-1 shot in the racing office, our pill came up. Just like that, we were in business. If we still read physical newspapers and took photos with cameras that were just cameras, I might have this framed on my office wall. But instead, I cut-and-pasted this here.

It is a digital “souvenier” of the event that made me a racehorse owner. Along with several experienced owners and others like me who were new to this part of the game.

How it started, how its going

What happened with Swaggish over the next few months was, in retrospect, exactly what those of us who are not lifelong horsemen needed. I’ll continue the Swaggish story in an upcoming post.

As of this writing, he’s still a happy member of our stable, as you saw in the picture at the top of this article. But this is claiming, where you control which horses you own, buy and sell. Up to a point, that is.

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.

If you want to keep up with what we’re doing, follow us here at HorseClaiming.com on Substack.