Expert Pick of the Week: 2025 Chicago Stakes

Jun 19, 2025

Emery wins the Leslie's Lady Overnight Stakes at Churchill Downs. (Photo by Coady Media)

A deep field of 11 fillies and mares will travel seven-eighths on the Churchill Downs dirt in Saturday’s $300,000 Chicago S. (G2). The Brad Cox-trained Emery was assigned a tricky draw on the inside of the big cast, but the four-year-old has the speed from the gate to overcome a troubled voyage, and I expect her to take down this talented group under Florent Geroux.

By More Than Ready, the filly has compiled a 10-5-3-0 lifetime line to date and has obvious room for improvement while being relatively lightly raced at this stage of her development. The Kentucky-bred miss is a stakes winner on the course and comes off of a decent try in a fantastic field when fifth in the Derby City Distaff S. (G1) on May 3.

The Grade 2 victress comes in fresh with positive morning drills in advance of this heat, and she has good early foot in a field lacking an abundance of pace, as well. If the Stonestreet color bearer is in the first or second flight early in the affair, then I envision her being tough to deny inside the final furlong.

Emery takes the G2 Lexus Raven Run at Keeneland for trainer @bradcoxracing with @tyler_gaff aboard! 🏆

🎥 #TwinSpiresReplay pic.twitter.com/GwHYnK9uZd

— TwinSpires Racing 🏇 (@TwinSpires) October 19, 2024

My Mane Squeeze is two-for-two beneath the Twin Spires while drawing off to graded stakes tallies on each occasion for trainer Mike Maker. The dark bay daughter of Audible commenced her 2025 campaign with a solid third in the Madison S. (G1) at Keeneland, prior to coming home a clear third in the Ruffian S. (G2) at Aqueduct at one mile last time out. She has won or placed in each of her seven career engagements at the seven-eighths voyage, and the four-year-old will be moving into contention approaching the turn for home with Luis Saez signed on.

Grade 1 queen Vahva suffered her first local setback from five tries when unplaced in the Derby City Distaff (G1) most recently for trainer Cherie DeVaux. By Gun Runner, the mare surely could have needed a run off the long layoff and will move forward in a big way on Saturday with something resembling her best effort. The Kentucky-bred five-year-old has recorded a quartet of very good half-mile morning drills in anticipation of the affair and will have Irad Ortiz, Jr. in the controls.

Expert Pick

An exacta with #1 Emery on top of #5 Vahva and #9 My Mane Squeeze in the 2025 Chicago Stakes is the Best Bet of the Week.