New Jack was involved in the Mass Transit Incident on November 23, 1996 in Revere, Massachusetts. The Gangstas were scheduled to face D-Von Dudley and Axl Rotten. For whatever reason, Axl Rotten could not make it to the show (In the 2005 documentary Forever Hardcore, New Jack said he thinks something happened with Axl's grandmother, which forced Axl to not make it). Rotten was replaced with "Mass Transit" Eric Kulas, an untrained seventeen-year-old who convinced booker Paul Heyman that he was nineteen and had been trained by the veteran Killer Kowalski. In the course of the match, New Jack attempted to blade Kulas (at Kulas' request), but Kulas flinched causing New Jack to cut through an artery, causing him to begin bleeding profusely. Kulas was hospitalized as a result, eventually receiving fifty stitches. New Jack was charged with aggravated assault stemming from the incident, but was acquitted. Kulas subsequently sued New Jack and ECW for damages in July 1998, but lost the case.
On March 13, 2000, New Jack (legitimately) suffered brain damage and was permanently blinded in his right eye when he and his opponent, Vic Grimes, fell off a 15 foot 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) at ECW Living Dangerously 2000. In a rematch between the two in Xtreme Pro Wrestling (XPW), New Jack threw Grimes off of a scaffold, with Grimes plummeting forty feet into the ring. The stunt did not work out as planned, as Grimes did not go through all twelve tables that were intended to break his fall and ended up dislocating his ankle on a rope. In the 2005 documentary Forever Hardcore, New Jack claimed that he had intentionally thrown Grimes too hard in the hopes that he would hit the ringpost and for Grimes to be injured or die. Also in the interview he blamed Grimes for his head trauma and blindness in his right eye for pulling away before the fall causing him to come down afterwards on his head instead of body to body.
After ECW declared bankruptcy in April 2001, New Jack began wrestling on the independent circuit. In 2002, he wrestled for XPW, and in 2003, he made multiple appearances with Total Nonstop Action Wrestling, and also Combat Zone Wrestling, competing in Cage Of Death 5. On October 9, 2004 he was arrested following a match in Jacksonville, Florida in which he repeatedly stabbed his opponent (the charges were later dropped after the victim insisted that the stabbing was planned). New Jack appeared at the ECW reunion show, Hardcore Homecoming, on June 10, 2005, and was allegedly scheduled to appear at One Night Stand two days later, but was prevented from entering the state of New York due to an outstanding warrant.
On September 13, 2006, New Jack was involved in an altercation at a Pro Wrestling Xplosion event at the New Alhambra Arena. According to various reports New Jack became physically involved with a security guard after he was given a 7-Up instead of a Sprite at the concession stands. When another staffer attempted to calm him down there was a "physical incident" which lead to over twenty police officers being called to the scene to restrain him. Later in the night, Ian Rotten called out New Jack, causing some tension between the two as New Jack has made public comments challenging Ian Rotten to a street fight, not in the ring.
New Jack was not arrested, as the person he became physically involved with declined to press charges. He was, however, removed from the venue by the responding police officers after gathering his belongings.