According to an interview in the
Sunday World with his ex-wife Anne Tedford, to whom a youthful Gray was married for four years (a marriage that produced one son, Jonathan), Gray joined the loyalist paramilitary
Ulster Defence Association (UDA) when she was in maternity hospital. She claimed that Gray was offered a lift home by a near-neighbour, Gary Matthews, who was already a UDA member, and that Matthews had Gray sworn in as a member soon afterwards. He eventually rose to become brigadier of the East Belfast Brigade, taking over after
Ned McCreery was killed by the UDA in 1992.
Brigadier Nicknamed "
Doris Day" and the "Brigadier of Bling", Gray, who was 6'3" in height, became known as the most flamboyant leader in the UDA with his dyed blond bouffant hair, permanent suntan, gold earring, ostentatious jewellery, and expensive pastel clothing. In their book
UDA – Inside the Heart of Loyalist Terror, journalists
Henry McDonald and Jim Cusack described him as "looking more like an ageing
New Romantic" than the leader of a paramilitary organisation. He once attended a UDA meeting with the
Secretary of State for Northern Ireland,
John Reid, wearing a loud Hawaiian-print shirt with a pink jumper draped over his shoulders. A heavy cocaine user, Gray made large amounts of money from selling drugs, protection racketeering, and extortion. Renowned for his violent temper, he once allegedly brutally beat then stomped on a man's head during an outdoor
Rod Stewart concert at
Stormont in full view of the audience. On another occasion, he violently attacked a man with a golf club after the latter had beaten him in a game of golf. For that assault, Gray was barred from the Ormeau Golf Club. After the killing, Legge's body was placed in a carpet and dumped outside Belfast. Legge's knife wounds were so severe that his head was almost severed from the body. The pub was set on fire to eliminate the signs of the torture that had been carried out inside. Gray was one of the mourners who attended Legge's funeral. The following year on 13 September 2002, Gray was shot in the face by UDA rivals; the plastic surgery to repair the considerable facial injuries cost £11,000. The shooting, which was blamed on
West Belfast Brigadier
Johnny Adair, Adair had previously started a whispering campaign against both Gray and
John Gregg of the
UDA South East Antrim Brigade, claiming both men were to be stood down as part of his attempts to take full control of the UDA. As part of this Adair, who was close to the LVF, had visited the Warnock family and suggested that Gray had been involved in their relative's death (which had actually been carried out by a hired
Red Hand Commando gunman after Warnock refused to pay a drug debt to a North Down businessman). As a result, Gray was shot by a lone gunman after he left the Warnock home, where he had been paying his respects to the deceased. On 25 September, Gray discharged himself from the
Ulster Hospital to attend a meeting of all the brigadiers bar Adair at which he, John Gregg,
Jackie McDonald,
Billy McFarland and
Andre Shoukri found Adair guilty of treason for his role in Gray's shooting and released a press statement to the effect that Adair was expelled from the UDA. Two weeks after the attack, Gray flew to
Tenerife for a holiday. He allegedly owned property in Spain. Gray's son, Jonathan, died of a drugs overdose in 2002 while with his father on holiday in
Thailand. An October 2005 report by the
Belfast Telegraph claimed that Jim Gray was bisexual and would regularly
take holidays to Thailand to have sex with teenage boys. ==Expulsion and arrest==