BY STEVE KOCH

The Florida-bred Old Chestnut will attempt to add another graded stakes victory to his resume in Saturday’s $200,000 bet365 Highlander Stakes (Grade 2) at Woodbine. The 8-year-old son of Speightstown enters the six-furlong turf contest at 15/1 on the morning line, coming off a triumphant performance in the Jacques Cartier Stakes (Grade 3) on May 31.

Bred by Live Oak Stud and now owned by Bruno Schickedanz, Old Chestnut has compiled a record of 6-5-7 from an extensive 42 career starts with earnings of $432,262 under the care of trainer Martin Drexler. The veteran campaigner has shown particular affinity for Woodbine, where he captured the Jacques Cartier Stakes last month after finishing third in a starter optional claiming race at Gulfstream Park in March. His recent success marks a return to form following a disappointing 10th-place finish in an allowance optional claiming race at Gulfstream in January.

The bet365 Highlander Stakes brings together eight horses for the six-furlong turf sprint with post time scheduled for 5:06 p.m. EDT on Saturday. The race is restricted to four-year-olds and upward, creating a competitive field that will test Old Chestnut’s ability to compete against younger, highly regarded opponents. The Florida-bred has previous experience in this race, finishing eighth in the 2024 edition and fourth in 2023, while also placing second in the Jacques Cartier Stakes in 2024. Eswan Flores will guide Old Chestnut from post position seven at 122 pounds.

The field lines up from the rail out with My Boy Prince (Sahin Civaci, Mark Casse) breaking from post one, followed by Playmea Tune (Rafael Hernandez, Josie Carroll) in post two, Niagara Skyline (Dylan Davis, John Charalambous) in post three, Its Time to Shine (Jose Campos, Jon Ross) in post four, morning line favorite Patches O’Houlihan (Sofia Vives, Robert Tiller) in post five, Ms. Tart (Huber Villa-Gomez, Kevin Rice) in post six, Old Chestnut (Eswan Flores, Martin Drexler) in post seven, and Dresden Row (Ryan Munger, Lorne Richards) completing the field from the outside post.

The morning line establishes Patches O’Houlihan as the 6/5 favorite for trainer R.P. Tiller. The 5-year-old Ontario-bred boasts an impressive record of 12-1-0 from 15 career starts with earnings of $748,590, including a 2025 victory in the Thorncliffe Stakes. My Boy Prince follows at 5/2 after finishing second in the Grade 1 Jaipur Stakes at Saratoga on June 8, while Playmea Tune rounds out the top three choices at 9/2 following his victory in the Forego Stakes at Turfway Park in February. Dresden Row enters at 6/1 as the only other single-digit choice in the competitive field.

Parts of this article were drafted with Claude.ai.

Return to the June 27 issue of Wire to Wire