On the October 22 episode of "ECW on TNN", Jack received his first opportunity for the World Heavyweight Championship against Mike Awesome but failed to win the title. On the November 5 episode of "ECW on TNN", Jack rescued Hardcore Chair Swingin' Freaks from an attack by Da Baldies (The Spanish Angel, Vito LoGrasso, Tony DeVito and Vic Grimes) but Angel stapled Jack in the eyes. This led to a lengthy rivalry between Jack and Angel over the unofficial title of "King of the Streets". The two battled back and forth over the matter in bloody street fights. One of ECW television's most gruesome moments was when in the course of a match, Angel used New Jack's staple gun (which he often wore around his neck with a chain) against him, stapling him in the eye. Referees called off the match, and New Jack disappeared from the air for many months. New Jack returned by the end of 1999 with his eye seemingly recovered, now sporting a scythe around his neck, claiming that he had "upgraded" the staple gun.