Zipse: Stilleto Boy is back for more in the Stephen Foster

Photo: Benoit Photo

He does not win often, but since being purchased two summers ago, Stilleto Boy has been a check-cashing machine. The chestnut gelding will be back at it again Saturday in search of his second career Grade 1 victory in the $1 million Stephen Foster at Ellis Park.

In what could easily be called the best field ever assembled at the Henderson, Ky., oval, Stilleto Boy will be one of seven runners who have scored graded-stakes wins this year. In fact, the only horse in the Foster field not to win a graded stakes this year, Speed Bias, missed by a nose last out in the Pimlico Special (G3).

It won’t be easy for the son of Shackleford, but tough fields are nothing new for him. Stilleto Boy has faced all comers for trainer Ed Moger Jr.

Moger conditions the 5-year-old gelding for his brother, Steve, who bought him for $420,000 at the 2021 Fasig-Tipton July selected horses of racing age sale soon after an upset win in the Iowa Derby.

The Foster will be the 10th Grade 1 race for Stilleto Boy since the purchase. Truly a horse who dances every dance, he finally broke through at the highest level in his most recent attempt, when he won a thriller over top older horses Proxy and Defunded in the Santa Anita Handicap (G1).

   

Squeezed a bit heading into the first turn, pinned on the rail early, then stuck between horses before swinging wide for the turn under rider Kent Desormeaux Jr., it was an underrated performance for an underrated horse.

As a son of Shackleford, it should come as no surprise that Stilleto Boy is as tough as a two-dollar steak. Like his sire, whom he resembles, the Grade 1 winner is always up for a fight.

Like his son, Shackleford didn’t always win. He was 6-for-20 lifetime, but trying to get by him in the stretch proved to be a major chore. In Grade 1 races such as the 2011 Preakness and the 2012 Met Mile and Clark Handicap, the chestnut with the white blaze simply would not be denied.

Stilleto Boy is not there yet, but in a wide-open older male division headed to the Breeders’ Cup Classic in November at Santa Anita, he has a chance to become remembered like his sire.

He’s had only one race since that Big 'Cap score in March, and once again, Stilleto Boy showed up. The occasion was the Oaklawn Handicap (G2), and this time Proxy got the best of him. But the California shipper proved a dogged competitor. Leading for much of the way, he was beaten only a head and a nose at the wire.

Given 10 weeks between races after a tough early season stretch, Stilleto Boy should be primed and ready for his return to the races Saturday.

His season began the same way it did last year, with a trip east for the Pegasus World Cup (G1) at Gulfstream Park. For the second consecutive season, he finished third in the rich race at odds higher than they should have been.

It’s rare these days to see a horse running in as many big races as Stilleto Boy does. The fact that he is only 4-for-24 lifetime and is as popular as he is tells you something. This horse tries, and he seems to be in career best form now as a 5-year-old.

Often a hard-hitting participant in America’s biggest races the last few years, Stilleto Boy has never been considered “the horse.”

That could all change on Saturday at the unlikely location of Ellis Park. As usual, he will not be the favorite, but as always, he will be in with a big chance.

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