Stilleto Boy

Stilleto Boy started his racing career on the Midwest circuit and broke his maiden at Oaklawn Park in April 2021. The Shackleford gelding scored his first stakes win in the Iowa Derby at Prairie Meadows on July 2 and shortly after was purchased for $420,000 by Steve Moger at the Fasig-Tipton July Horses of Racing Age sale.

Transferred to Moger's brother Ed in California, Stilleto Boy ran fifth and third in two stakes races at Del Mar (the first on turf, the second on dirt) before turning in arguably his best race in the Grade 1 Awesome Again Stakes at Santa Anita Park on Oct. 2, when he finished second by five lengths to Medina Spirit at odds of 54.80-1. That effort gave the Mogers confidence to point the Shackleford gelding to the Longines Breeders' Cup Classic on Nov. 6 at Del Mar. 

In the Classic, Stilleto Boy had no rally late and finished fifth, beaten ten lengths by Knicks Go. He wrapped up his 3-year-old season with a third-place finish in the Grade 1 Runhappy Malibu Stakes at Santa Anita on Dec. 26. 

After finishing third in his first two starts of 2022, Stiletto Boy picked up his first win of his 4-year-old year on Apr. 30, when he won the Grade 2 Californian Stakes in gate-to-wire fashion. Odds-on favorite Express Train pressed him throughout, but Stiletto Boy held him off and secured the win. He followed that win up with a fourth-place effort in the Hollywood Gold Cup Stakes at Santa Anita on May 30, tiring late after stalking the early pace. He closed out his 4-year-old campaign with a runner-up finish in the Grade 2 San Antonio Stakes Dec. 26 at Santa Anita Park.

Stilleto Boy kicked off his 5-year-old season with a third-place finish in the $3 million Pegasus World Cup Invitational Stakes Presented by Baccarat Jan. 28, 2023, which matched his effort from the previous edition.

Stilleto Boy returned to southern California for his next start, which would come in the Grade 1 $500,000 Santa Anita Handicap at the classic distance of 1 1/4 miles on the main track. Sent off at 13-1 odds on the tote board from post 3 in a nine-horse field in the 'Big Cap', Stilleto Boy stalked the pace throughout and was never too far back off the pace at any point in the race. He moved into striking position in mid-stretch under jockey Kent Desormeaux and then came on to finish strong to prevail by a neck in a winning time of 2:01.96.