Bosun, a four-year-old New York-bred by Midshipman out of Kipling’s Joy, punched his ticket to bigger things with a sharp allowance win on the Saratoga turf July 19. Rallying from mid-pack with a strong six-wide move, he surged past rivals late to score by 2 1/4 lengths in 1:01.65 for 5.5 furlongs earning a career-best 94 Equibase Speed Figure in the process.

Ridden by Jose Ortiz for trainer Joe Sharp and owner Highlander Training Center, the gelding earned $52,250 for the win, boosting his career total to $120,510 from just six starts.

From Modest Beginnings to Market Hit

Bosun didn’t leap off the page as a yearling, bringing just $57,000 at Saratoga. But his physical caught up to his pedigree by the time he breezed at Timonium. That performance helped him bring $225,000 at the Fasig-Tipton Midlantic 2-Year-Old Sale, purchased by Clark Shepherd of Shepherd Equine Advisers on behalf of Highlander’s Larry Hirsch.

Bosun was one of Shepherd’s OPTIMAL Mating Sale Selections and now he’s validating that label on the racetrack.

Pedigree Power, Hidden in Plain Sight

Bosun’s pedigree was never about flash. But for those willing to look deeper, it’s quietly packed with quality. He’s inbred 5×4 to Mr. Prospector, with reinforcing lines to Prince John, Buckpasser, Bold Ruler and Hail to Reason balanced across generations, with a COI of just 0.561% and an outcross rate of 86.66%.

He hails from Female Family A11, a line more known for durability than glamour. His dam, Kipling’s Joy, was a four-time stakes-placed winner who banked over $185,000. She’s by Kipling, best known as the sire of Kip Deville and traces back through solid, hard-knocking female stock. It’s a family that needs the right mating and a little patience. Bosun may be that payoff.

What Could Be Next for Bosun

With two wins and two seconds from six starts and top figures improving each time, Bosun has likely earned a shot against open company. His ability to close on turf and his competitive nature suggest there’s more in the tank.

Whether that means a state-bred stakes, a try in open allowance, or even a cut at something black type, Bosun is starting to look like more than just a useful New York-bred. He might just be a runner with upside.

For now, his connections can take pride in a well-executed plan. But if his pattern holds, Bosun may have more to say before the year is out.

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Clark Shepherd Bloodstock Agent, Sales Consultant & Pedigree Analyst

Clark Shepherd stands as a beacon in the thoroughbred world, renowned for his unyielding integrity and deep-seated expertise. Growing up on the racetrack, he transformed his lifelong passion into a thriving career as a trusted bloodstock agent. Clark's profound knowledge in equine management and keen eye for racehorses have led numerous clients to victory, including the pinnacle of designing the mating of a Kentucky Derby winner. Dedicated to both industry stalwarts and newcomers, he offers personalized, insightful guidance in every equine venture. Clark's ethos is encapsulated in his mantra: "Empowering Equine Success with Integrity and Insight!"

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