It is not as certain as taxes and the sun rising in the east, but trainer Chad Brown winning the Jenny Wiley (G1) in recent years has been almost a certainty.

Brown has won five of the past six runnings of the 1 1/16-mile turf race for fillies and mares and has six Jenny Wiley victories overall. On Saturday, he has four of the race’s 10 entrants: Peter Brant’s Gina Romantica, Klaravich Stables’ Surge Capacity, Madaket Stables and Louis Lazzinnaro’s Beaute Cachee (FR) and Head of Plains Partners’ Fluffy Socks.

Three of Brown’s six Jenny Wiley winners made their season debuts in the race.

“With a lot of my good grass fillies, I like to target this and I like the mile and a sixteenth to start,” Brown said.

Only Fluffy Socks has run this year. She finished fourth in the 1 1/16-mile TAA Pegasus World Cup Filly and Mare Turf Invitational (G2) at Gulfstream Park in January and was third in the 1 1/8-mile Hillsborough (G2) at Tampa Bay Downs in March. 

“That was a little far for her,” Brown said about the Hillsborough.

The established star of Brown’s 2024 quartet is Gina Romantica, who could make a bit of Keeneland history with a victory in the Jenny Wiley.

Gina Romantica, the 3-1 morning line favorite in the Jenny Wiley, has won two turf stakes at Keeneland: the 2022 Queen Elizabeth II Challenge Cup (G1) Presented by Dixiana and the 2023 First Lady (G1) Presented by UK HealthCare both during the Fall Meets.

A victory Saturday would make Gina Romantica the fourth horse to win three separate Grade 1 races at Keeneland and the first to do it without a Breeders’ Cup victory. The horses who have accomplished the feat are Tepin (First Lady, Breeders’ Cup Mile and Jenny Wiley), Essential Quality (Breeders’ Futurity, Breeders’ Cup Juvenile and Toyota Blue Grass) and Malathaat (Central Bank Ashland, Spinster and Breeders’ Cup Distaff).

“We know she loves Keeneland,” Brown said of Gina Romantica, who finished fourth beaten a length by males in the FanDuel Breeders’ Cup Mile (G1) Presented by PDJF at Santa Anita to conclude her 2023 campaign. “She ran super in defeat.”

Brown’s other three Jenny Wiley entrants closed 2023 with a 1-2-3 finish in the Matriarch (G1) at Del Mar on Dec. 3. Surge Capacity won the race by a head over Fluffy Socks with Beaute Cachee 1½ lengths back in third.

In her race before the Matriarch, Surge Capacity won Keeneland’s Bank of America Valley View (G3) on turf.

“I think all four of them have a good shot tomorrow,” Brown said about his Jenny Wiley quartet.