After co-winning Tough Enough III with John Hennigan, he worked in Ohio Valley Wrestling (OVW), the primary developmental territory for WWE.

Cappotelli, along with John Hennigan, won a World Wrestling Entertainment (WWE) contract by winning Tough Enough III.

[2] During the show Hardcore Holly aggressively roughed up Matt while training, stiffly striking Cappotelli repeatedly, leaving him bleeding.

On February 8, 2006, he announced that he had previously been diagnosed with a grade 2/3 astrocytoma and surrendered the title to OVW owner Danny Davis at a television taping in Louisville, Kentucky.

[6] Cappotelli announced to OVW wrestlers and fans on April 4, 2006, that he would undergo surgery for brain cancer in Boston on May 1.