A year after the Infinite Crisis, Thomas proposed that the group bet on whether "the ultimate noble hero" could withstand "the ultimate ignoble defeat", the Black Glove targeted Batman as their next victim.
Having been watching his descendant over the years, Thomas had fully prepared for the time when he and Batman would engage each other, posing as Doctor Simon Hurt and assisting Batman in various psycological experiments near the beginning of the hero's career. During the experiments, Thomas inserted various psycological commands into the hero's mind to use at a later date.
Following Wayne's return from a one year sabaticle after the Infinite Crisis, Jezebel Jet, former fashion model, leader of a small African country and secretly a member of the Black Glove, meets and forms a relationship with Bruce Wayne in London; a relationship that is closely monitered by Talia al Ghul.
As the first salvo, Thomas activates the "Three Ghosts of Batman", a failed experiment involving three men originally chosen from the police force to train with Batman to replace him should anything happen to him.
The first "ghost", the Bat-Cop, decided to "clean up the city" using vigilante methods. He attacked the Joker, who believed him to be the real Batman, but was beaten within an inch of his life before managing to shoot the villain in the face.
The second "ghost", the Bat-Bane, attacked the Batman after the hero had tracked him down following a string of prostitute murders.
The third "ghost", the Bat-Devil, aggressively attacked the hero and shot him in the chest with such force as to stop the hero's heart. Captured and on the verge of being tortured to death, Batman managed to defeat the imposter and escaped to recuperate at Wayne Manor.
During the salvo, Wayne and Jet's relationship strengthens as Jet "discovers" Bruce's alterego as Batman and is invited into the Batcave.
As the second salvo, Thomas instructs fellow Black Glove member John Mayhew to draw the disbanded hero group, the International Club of Heroes, to his island and enacts a psuedo murder mystery which involved the murdering various members of the group and challenging Batman to find the killer before all of them are killed. While The Musketeer, Legionary, and The Ranger were killed, and Wingman was revealed to be in league with the Black Glove also, Batman ultimately prevailed and Thomas Wayne executed John Mayhew as the consequence for losing the bet.
Elsewhere, Commissioner Gordon tries to convince a local newspaper into not running a story on a dossier that was allegedly compiled by a detective hired by the parents of Martha Wayne. The dossier is said to contain evidence that Alfred Pennyworth is Bruce Wayne's true biological father and that Thomas Wayne was a drunk who got his wife Martha addicted to heroin. The dossier is also said to contain photographs of an orgy involving Thomas and Martha Wayne, Alfred, and the stars of a noir film "The Black Glove" and that Thomas Wayne may still be alive and that the "murder" of his wife Martha was part of an elaborate scheme to kill his unfaithful wife and fake his own death.
While Bruce begins to suspect a hidden group operating behind the "ghosts" and the island, Thomas assembles a varient of the International Club of Heroes, made up of the various arch nemesis of the former group, including the Joker, and dubbing it the "International Club of Villains".
He has the group assault Wayne Manor and capture Nightwing and Alfred Pennyworth but misses Robin, while Batman is incapacitated in the cave by one of Thomas' trigger words uttered by Jezebell.
While Thomas targets Batman's associates, destroying the Outsider's safehouse and severly injuring the group, he injects Bruce with weapons-grade crystal meth and releases him onto the city streets.
Imprisoning Nightwing in Arkham Asylum, the Black Glove initiates a massive crime wave in Gotham as Bruce pieces together a back-up personality, the "Batman of Zur-en-Arrh", and makes his way to Arkham where he confronts the Joker and Jezebel reveales her treachery.
As Thomas buries Batman in a shallow grave with the intention of exhuming him once oxygen deprivation has permanently damaged his mind, the Joker places a bet with the Black Glove that Batman will emerge from the grave undamaged and hunt them down, as he always does.
When Batman, Nightwing, Robin, Damian, and the League of Assassins converge on the group, the Joker flees in an ambulance and promises the remaining Black Glove members that he will collect his winnings from them soon. Thomas Wayne was thought killed while escaping in a helicopter.
The following months saw the occurance of the Final Crisis and the deaths of many members of the Black Glove due to retribution from Talia al Ghul and the Joker. Within six months, most of the Black Glove was dead at the hands of the League of Assassins, Jezebell Jet had been captured by Talia's Ninja Man-Bats, and the Joker had taken up a new identity as Oberon Sexton; hunting down and killing members of the group as winnings for his bet.
Disguised as the drug lord El Penitente, Thomas later returns to Gotham City to finish the attack. With the Joker working as an unreliable ally, Hurt used the Circus of Crime to release a drug into Gotham's air with the intention of driving the city mad, subsequently making a public return as Thomas Wayne with the intention of setting up his headquarters in the Batcave.
Capturing Dick Grayson, who was now Batman thanks to Darkseid having sent Bruce Wayne into the past during the Final Crisis, Thomas shoots Grayson in the back of the head and attempts to force Damian Wayne to swear allegiance to him in order to save Grayson's life. However, Grayson and Damian had already anticipated his attack and Bruce reveals himself and joins his wards in combating Thomas' forces.
Hurt attempts — and fails — to trap Bruce Wayne in a prison in the Batcave, but nevertheless escapes through the cave's water access while Bruce is busy rescuing Alfred. Having escaped to a graveyard, Hurt is confronted and defeated by the Joker, when he slips on a banana peel and breaks his neck. The Joker doses Hurt with Joker venom and buries him alive, claiming that he proved to be a disappointment as a 'new' arch-enemy.
With the "death" of Thomas Wayne, the Black Glove is believed to have been abolished and the Circus of Evil was incorporated into the Leviathan group.