Their first encounter was at November to Remember, where Jack and the Freaks lost to Da Baldies in a handicap match. At the 2000 Guilty as Charged pay-per-view, Jack lost a singles match to Angel due to interference by Da Baldies. At the Living Dangerously live pay-per-view in Danbury, Connecticut on March 12, New Jack suffered serious injuries during a match against Vic Grimes involving a bump that required them to jump and fall 15 feet off a scaffold. Mere seconds before the jump, Grimes became reluctant to take this very risky bump, and New Jack, annoyed with Grimes's reluctance (because of the live broadcast they had no time to improvise) dragged Grimes down with him after a count of 3, and Grimes awkwardly fell half a second after Jack instead of falling together in the safest fashion. They fell off the scaffold, missed the tables that were supposed to absorb the force of their fall and landed on the concrete floor, with Grimes landing on New Jack's head. New Jack suffered legitimate brain damage, a broken leg, a skull fracture (resulting in permanent insomnia) and was permanently blinded in his right eye, and spent 6 months recovering, but even while injured Jack defeated Da Baldies leader Angel in a match 2 months later at Hardcore Heaven.