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2006 Dark Bay or Brown Colt
| Trainer: Angel O. Montano, Sr. | |
| Jockey: Miguel Mena | |
| Owner: Two Dimes Stable | |
| Breeder: Destinaire Farm |
| Smarten Destiny | Smart Strike | Mr. Prospector |
| Classy 'n Smart | ||
| Valenza | Chief's Crown | |
| Soli |
Prices in parentheses indicate a horse did not sell because it did not meet its reserve price.
| Year | Sale | Price |
|---|---|---|
| 2007 | Fasig-Tipton New York Saratoga 2007 Select Yearling Sale | ($70,000) |
Headache charged home late to capture the $138,000 Claiming Crown Jewel at Canterbury Park July 24, giving owners Ken and Sarah Ramsey, trainer Mike Maker and jockey Julien Leparoux back-to-back wins in the main events.
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