Bamboozler sold as a yearling for $16,000 and again as a two-year-old for $40,000.
He made his racing debut as a two-year-old in August 2019. He was vanned off during his second race after clipping heels. He was unharmed and returned to racing in November.

Bamboozler sustained a completely displaced lateral condylar fracture of the right front limb during work on February 15, 2020. Surgery was performed the next day.
He was rechecked by a veterinarian, and he has healed well. He can start retraining for a second career.