Race 9 at Churchill Downs | Saturday, June 21 | Post Time 10:11 PM Eastern

Chicago Stakes – Grade 3 | Purse $300,000 | Seven Furlongs | Fillies and Mares, Four Years Old and Upward

Top Contenders: Emery (1), Zeitlos (11), My Mane Squeeze (9)

Emery (1) is a grade 2 stakes winner in a grade 2 race, having won the Raven Run Stakes last fall at Keeneland, which was also run at this seven-furlong distance. That was just one of four wins last year in five races, with her only runner-up last year coming in the Grade 1 Test Stakes. She then missed by a head in the identical grade 2 Inside Information Stakes in late January and missed by a length in the higher level Grade 1 Madison Stakes at this distance in April. Notably, last year’s Chicago Stakes winner, Vahva (5), also finished second in the Madison. Since the Madison, Emery finished fifth in the Derby City Distaff, run over a very wet and sloppy (sealed) track on Kentucky Derby day. I’m willing to ignore that race because Emery’s record suggests she is so very good otherwise. Prior to the Derby City Distaff, Emery won her only start at Churchill Downs, last June in the Leslie’s Lady Stakes at this distance, where she’s never finished worse than second in six career starts. Although she finished fifth in the Derby City Distaff, that race has turned out to be productive, as the second and eighth place finishers came back to finish second and third in the Winning Colors Stakes. Better still, the third place finished (Ways and Means) won the Bed O’ Roses Stakes, in which Derby City fourth place finisher was second. This really suggests Emery is going to rebound to top form good enough to win this race.

Zeitlos (11) has won four of six at Churchill, but unlike Emery, she has not run many races at this distance in her career, two to be exact in 18 career starts. She’s rarely run farther than six furlongs but did win the Open Mind Stakes over the track last September at six and one-half furlongs. Coming off a six-month layoff about four weeks ago, Zeitlos won the Skipat Stakes, a non-graded stakes race, on Preakness day, and she is likely to improve second off the layoff. She gets a good post and a likely fast early pace to close into (same as Emery) with Gray Lightning and a couple of others being very fast in the early stages. If not for the concern this isn’t a distance she’s proven at, Zeitlos might be my top choice.

My Mane Squeeze (9) is another top female sprinter, with six wins in 145 starts and over $1 million in earnings (similar to Zeitlos). She’s two for two at Churchill Downs including a win in the Eight Belles Stakes on Kentucky Oaks day last year at this distance and under Saez, who gets back on after two races with another jockey. On the other hand, at this distance her record is 2-2-3, and in her only two starts this year, My Mane Squeeze has been in front or within a neck of the lead with an eighth of a mile to run but has finished poorly, ending up third both times. Last, but not least, in three races in which she’s faced Emery previously, My Mane Squeeze has finished behind Emery, although in today’s race she gets five pounds less than Emery, which may help her to perhaps turn the tables on that one.

Pigalle (8) is an interesting horse and likely to be higher odds than the main three contenders, so has to be considered. She’s won six of 13 including three of seven at Churchill Downs, and she finished second over this track in two other races. She won the Goupie Doll Stakes last Summer at Ellis Park when Machado first rode her, and Machado rides her again after being aboard for a win on May 30 in her first start of the year and after six months off. Pigalle is likely to improve second off the layoff and can’t be counted out at a price.

Now, as to Vahva (5), who has six career wins in 16 races and earnings of more than $1.8 million, and who has won four of five at Churchill Downs and five of 10 at this distance. I think she may be a bit suspect here and I am taking a stand against her. She won this race last year after winning the Derby City Distaff then finished third and sixth in her final two starts of 2024. In her 2025 debut in this year’s Derby City Distaff, Vahva faded to seventh and never really showed the type of energy she had in most of her races last year and the year before. She may be off form, and in that case, as she is likely to go to post at odds of less than 5 to 1, I’ll try to beat her.

Win Bets:

Emery (1) should be considered first, at odds of 9 to 5 or more.

Zeitlos (11) and My Mane Squeeze (9) can be considered if their odds are 5 to 2 or higher.

Exactas:

Emery (1), Zeitlos (11) and My Mane Squeeze (9) over Emery (1), Zeitlos (11), My Mane Squeeze (9) and Pigalle (8)

Emery (1), Zeitlos (11), My Mane Squeeze (9) and Pigalle (8) over Emery (1), Zeitlos (11) and My Mane Squeeze (9)