Saturday’s First Lady at Keeneland may end up being the most competitive stakes event of the meeting outside the Breeders’ Cup, with eleven fillies and mares set to battle over the mile distance in Lexington, Kentucky. This year’s First Lady is as difficult a handicapping puzzle as you’ll find, with legitimate cases to be made for at least 75% of the field to come out on top. Annoyingly, my only advice is this: unless you absolutely love a horse, don’t “settle” on a short price. This race is far too salty to settle on a 2-1 or 3-1 shot; don’t be afraid to go out on a limb with a price in a spot like this.

Below you will find my fair win odds for each of the runners scheduled to compete in the G1 First Lady as well as my thoughts on some of the key contenders.

1 – Pin Up Betty / 2% / 49-1
2 – Lush Lips / 11% / 8-1
3 – Mandanaba / 11% / 8-1
4 – Expensive Queen / 14% / 6-1
5 – And One More Time / 8% / 12-1
6 – Deep Satin / 6% / 16-1
7 – Love You Anyway / 3% / 32-1
8 – Segesta / 14% / 6-1
9 – Classic Q / 11% / 8-1
10 – Bless the Broken / 14% / 6-1
11 – Vina Arana / 6% / 16-1

There are a million ways this analysis could begin; let’s start, though, with the runners who dead-heated for the win in the G1 Jenny Wiley here in the spring – SEGESTA (8) and EXPENSIVE QUEEN (4). Segesta is a track specialist, owning a record of 3-2-1-0 in three starts over Keeneland’s turf. The knock on the five-year-old mare, however, is her recent form. While still competitive against good company in New York over the summer, it’s fair to wonder if Segesta has regressed some over the course of 2026. If that’s the case, she’s probably settling for a minor award on Saturday.

Expensive Queen, on the other hand, is a bit of an unknown commodity in the First Lady. After the dead heat here in April, the daughter of Lope de Vega went to the sidelines and hasn’t been seen in a race since. Now, off a six-month layoff, the Brendan Walsh trainee will need to put her best foot forward in order to have her picture taken in the Keeneland winner’s circle for the third time in three races locally. She’s a major threat, but another where price must be your guide.

LUSH LIPS (2) and MANDANABA (3) are drawn just to the inside of Expensive Queen, and they both represent reasonable win candidates, too. Lush Lips has run just once since a victory at Gulfstream Park in February, but she’s already a grade one winner at Keeneland, having taken the Queen Elizabeth II Cup here last fall as a three-year-old. Her best races make her a serious threat to win this event.

The same can be said for Mandanaba, who finished a solid second in a group two event in Germany as a precursor to a start on Saturday. Trained by Francis Graffard, the four-year-old filly will be making her second stateside start of 2026 following a decent second in the G1 Just a Game at Saratoga during Belmont Stakes weekend. All in all, I didn’t think the trip was too bad for Mandanaba that day; pocketed up throughout, perhaps hemmed in a bit at the top of the lane…but then Classic Q floated more than a path off the rail and Mandanaba simply couldn’t fire through. She’s a threat on her best, but her best is probably necessary.

Speaking of CLASSIC Q (9) – she could be the speed-of-the-speed in the First Lady, a designation that is always dangerous. Her win in the Just a Game is clearly the best she’s ever run, and she’ll need a repeat performance if she’s going to take top honors in the First Lady on Saturday. She can win, but I chose to go with the horse who defeated her on the square when the two tangled at Kentucky Downs last month.

BLESS THE BROKEN (10) has run on turf only once in her fifteen-race career, but that turf try resulted in a victory over Classic Q and others in the G2 Kentucky Downs Ladies Turf on September 5. Sent off at 8-1 odds that day, the daughter of Laoban didn’t look especially strong around the bend but eventually found her best stride over the final quarter mile, kicking away from her contemporaries with relative ease. The flat mile at Keeneland is far from an apples-to-apples comparison, but I’m inclined to believe that her finish over the rise at Kentucky Downs will translate nicely to the turf in Lexington. I’m hopeful that Brian Hernandez, Jr. can have Bless the Broken in a tracking position down the backside before taking his shot at the pacemakers around the far turn.

THE PICKS: 10-4-8-2
THE PLAY: 10) BLESS THE BROKEN TO WIN AT ODDS OF 6-1 OR GREATER