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Jackie's Warrior × Sail On
2025 Jackie's Warrior × Sail On, Chestnut Colt. Foaled May 24, 2025.
Purchased for $110,000 at the 2026 Keeneland September Sale (Hip 394).
Consigned by Legacy Bloodstock, agent. Out of the Into Mischief mare Sail On, a sister to graded stakes-placed Colorful Mischief; fourth dam is Grade 1 winner My Flag, dam of champion Storm Flag Flying. A late-May foal with length and scope beyond a sprint-only type.
- Sire Jackie's Warrior
- Dam Sail On
- Color & Sex Chestnut Colt
- Trainer TBD
- Partnership Icon Racing: Sierra Leone
- Sale Catalog View Catalog Page →
Hip 394 · Keeneland September
How we bought Jackie's Warrior × Sail On.
Hip 394 was on our short list even though a sprint-oriented colt was not necessarily the profile we expected to emphasize at Keeneland. He is by Jackie's Warrior out of an Into Mischief mare, and both the physical and the pedigree gave us reasons to stay interested.
The important moment came when the bidding began to stall. We had already done the work and knew where we valued the horse, so the softer market gave us an opportunity to step in. We bought him for $110,000, comfortably below the level at which we were prepared to own him.
That is the kind of situation our process is designed to find: identify horses we genuinely want, establish our valuation before the auction pressure starts, and act decisively when the market gives us an opening.
The Dam Side
Sail On, by Into Mischief, is a sister to graded-stakes-placed Colorful Mischief and has already produced two winners from three starters. The second and third dams bring Distorted Humor and A.P. Indy into the female family.
The deeper page is unusually strong for this price point. The fourth dam is My Flag, the Grade I-winning daughter of Easy Goer and Personal Ensign. My Flag produced champion Storm Flag Flying, and the extended family contains a long list of Grade I performers. That gives the colt a deep foundation of elite American dirt blood behind a very speed-oriented sire.
The Physical
He is a late May foal, and the photograph reflects that: he is more leggy and less filled out than some earlier foals in the book. Even so, the frame is attractive. He has good length of neck and shoulder, a long hip and a clean, athletic outline.
Importantly, he does not look like a short, thick sprint-only model. There is scope here. The trade-off is that he still has developing to do through his body and topline, but that is exactly what one would expect from a May 24 yearling.
The $110,000 price becomes more interesting when the whole page is considered. The top line brings Jackie's Warrior speed, the dam is by Into Mischief, and the deeper female family runs directly into My Flag and Storm Flag Flying. The physical gives him enough length and scope that we do not have to assume the pedigree confines him to one dimension.
Physical comments are based on the sale photograph and are observations, not a substitute for live inspection or veterinary review.
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