Saffie Joseph, Jr. has owned the Princess Rooney Stakes for the past three years. On Saturday at Gulfstream Park, he will try to make it four straight—and he’ll have three chances to do it.
Joseph sends out Kerry’s Kiss (5‑2), Indy Bay (3‑1) and Anakarina (9‑2) in a field of seven for the $225,000 Princess Rooney (G3), the 7‑furlong centerpiece of Gulfstream’s fall Sunshine Meet and a Breeders’ Cup Challenge “Win and You’re In” race for the $1 million Breeders’ Cup Filly & Mare Sprint (G1) on Oct. 31 at Keeneland.
Joseph’s streak began with Three Witches in 2023, continued with eventual Eclipse Award champion female sprinter Soul of an Angel in 2024, and reached three last year with Haulin Ice.
If the home team is to be denied, the most likely spoiler may have come a long way to do it.
Simply Joking Ships East for Trainer Michael McCarthy
California‑based Simply Joking (the 8‑5 morning‑line favorite), trained by Michael McCarthy, brings the strongest graded‑stakes résumé into the Princess Rooney. The 4‑year‑old daughter of Practical Joke was most recently third in the Clement L. Hirsch Stakes (G1) at Del Mar and has finished in the money in five of her last six starts, all in graded company. She also finished third in the La Brea Stakes (G1) last December.
McCarthy knows the route from California to the Princess Rooney winner’s circle. He made it twice with champion Ce Ce, who shipped east to win the race in both 2021 and 2022.
But Simply Joking will have to get past a Joseph trio led by the rapidly improving Kerry’s Kiss.
The daughter of Vino Rosso has won three straight and already has beaten stablemate Indy Bay twice over the Gulfstream strip, taking the 6 1/2‑furlong Musical Romance in June, and the 7‑furlong Sheer Drama Aug. 15. Kerry’s Kiss has done her best work on or near the lead and figures to be prominent again Saturday.
Indy Bay, meanwhile, gets a third crack at her stablemate. The Grade 2 winner has three victories in five tries at 7 furlongs and, unlike Kerry’s Kiss, does not need the lead. That could become important if the Princess Rooney develops into a fight up front.
And there is reason to think it might.
Kerry’s Kiss has broken sharply in each of her recent starts, while rail‑drawn Anakarina also owns early speed. Anakarina enters off a victory in the Love Sign Stakes at Colonial Downs in her first start for Joseph. No Bad Beats, breaking from the outside, adds another potential pace presence.
The remaining starters are Just a Philly (20‑1), third behind Kerry’s Kiss and Indy Bay in both local preps; Chilean Group 1 winner Bombacha Veloz (15‑1), making her first start since November; and California shipper No Bad Beats (12‑1).
Race with a Breeders’ Cup History
The Princess Rooney’s connection to the Breeders’ Cup goes back much farther than its current “Win, and You’re In” designation.
The race itself honors Princess Rooney, winner of the inaugural Breeders’ Cup Distaff in 1984. And since the Filly & Mare Sprint was added to the Breeders’ Cup program, the Princess Rooney has repeatedly served as a stepping stone toward championship weekend.
In 2011, Musical Romance came within a neck of winning the Princess Rooney, rallying from far back only to be denied by favorite Sassy Image. Musical Romance went on to win that year’s BC Filly & Mare Sprint and the Eclipse Award as champion female sprinter.
A year later, she came back and finished the job, winning the Princess Rooney herself.
More recently, Three Witches earned her first stakes victory in the 2023 Princess Rooney and subsequently finished third at 35‑1 in the BC Filly & Mare Sprint. Soul of an Angel followed her 2024 Princess Rooney victory with a BC Filly & Mare Sprint triumph and the Eclipse Award.
That history gives Saturday’s winner considerably more than a Grade 3 trophy and a $225,000 purse.
She’ll also have a paid ticket to Keeneland—and a race that has proved more than once that the trip from South Florida to the Breeders’ Cup can be worth making.
The Picks: 1 Simply Joking, 2 Anakarina, 3 Kerry’s Kiss
| 2026 Princess Rooney Stakes Odds | |||
|---|---|---|---|
| 1 | Anakarina (KY) 9-2 | R Hughes | S A Joseph, Jr. |
| 2 | Kerry’s Kiss (KY) 5-2 | E Gonzalez | S A Joseph, Jr. |
| 3 | Simply Joking (PA) 8-5 | J J Hernandez | M W McCarthy |
| 4 | Just a Philly (FL) 20-1 | S Camacho | H Miller |
| 5 | Indy Bay (KY) 3-1 | M J Husbands | S A Joseph, Jr. |
| 6 | Bombacha Veloz (CHI) 15-1 | R Maragh | A M Sanchez |
| 7 | No Bad Beats (KY) 12-1 | D A Herrera | L Powell |
Last Updated on 09/11/2026
Jenny Kellner is an award‑winning journalist and teacher who has covered thoroughbred racing for years. As a reporter for both United Press International and The Associated Press, her work has appeared in publications and on websites around the world. Jenny has also written for The New York Times, the New York Post, Newsday and Sports Illustrated.
