At the 2016 Summer Paralympics in Rio, he won a fourth consecutive silver medal in the men's Long Jump - T11 event.

At the 2020 Summer Paralympics in Tokyo, he won a fifth consecutive silver medal in the men's Long Jump - T11 event.

Gillette was a part of the 2013 IPC Athletics World Championships 4 × 100 m relay team that won a silver medal and set a new American record in the process.

While in high school, Gillette was introduced to beep ball, a modified form of baseball for the visually impaired and blind.

The 2007 World Series of Beep Ball were held in Rochester, Minnesota, and the Dawgs returned to the championship game only to lose to the Kansas All Stars.

[4] In November 2015, Gillette received the Athletes in Excellence Award from The Foundation for Global Sports Development, in recognition of his community service efforts and work with youth.