Two-Face

Former District Attorney Harvey Dent was once Gotham's bright future, until half of his face was burnt with acid and his psyche damaged by one of his adversaries. Reborn as Two-Face, a criminal that relies on a coin toss to make his decisions, Harvey is now as dangerous as any man can be.

Road to Arkham
Two-Face was briefly mentioned by Oracle when Batman voiced his suspicions of the three anonymous tips upon apprehending the Joker, where she mentions that he was unlikely to have been the anonymous tipster as he was still hospitalized from an earlier encounter with Batman.

Batman: Arkham Asylum
After finally defeating the Joker, a call comes in over the police radios that Two-Face is robbing the Second National Bank in Gotham City. Batman then cuts his conversation with Commissioner Gordon short in order to pursue the criminal. The outcome of this implied confrontation between Batman and Two-Face is unknown, but it would seem that Two-Face would remain at large regardless months later.

After Arkham
Several months after the events of Arkham Asylum, Two-Face remained at large in Gotham City, continuing in leading his gang into making several heists. However, two former gang members of his, the brother, sister team T&T (based on his obsession with duality) begin operating on their own throughout Gotham. Batman correctly guessed that Two-Face hired the pair, who earlier that day attacked an armored car on its way to the bank. When Batman finds him, his left leg is broken, right arm is in a sling, and he's wearing a neckbrace with two hooker's at his side (each representing his two personalities).

He accepts Batman's deal for a thirty minute head start in exchange for information about T&T. He explains that following the Joker riots he bought several of the crates of Titan that had floated into Gotham docks saying that "the Coin said it was a good investment". Little did he realize the mistake of getting relatively new employee's T&T to bring it down into his basement. Upon realizing what they had they began training extensively in hand to hand combat and experimenting with Titan in small doses (thereby retaining control of themselves in Titan form). It wasn't long before they made their experiments known, slaughtering Two-Face's gang and nearly killing the man himself. He prevents his men from killing Batman, knowing they wouldn't be able to do it and more importantly believing T&T would.

Eventually, Hugo Strange would shut down all criminal operations throughout Gotham, forces many criminals and innocent civilians to flee the city, and capture every one of his targets except for three; Two-Face, Catwoman, and Batman. Two-Face, desiring to become the ruling elite on Gotham's streets, gives a tip to Professor Strange on where Selina Kyle resides. Using this information, Strange locates one of Selina Kyle's apartments where she was currently residing. Attacking the apartment, TYGER operatives were unable to capture Catwoman, but were able to locate her safe, full of stolen loot and goods. Under Strange's orders, the guards took the loot and goods to the Arkham City Confiscated Goods Vault, hoping that this would draw out Catwoman to be captured. True to Strange's prediction, Catwoman would set her sights on Arkham Island to obtain the blueprints for Arkham City that would allow her to locate the perfect entry level into the vault.

Unfortunately for Selina, Dent and his gang had the same idea and attacked the facility first, but Strange saw this as the perfect opportunity to capture the last two criminals on Gotham's streets. As Catwoman and Dent brawl for the plans, which Two-Face photographed with his camera, TYGER guards are sent in to apprehend them both. Batman, however intervenes and saves Catwoman just as she steals Dent's camera and Dent is arrested. Before Batman can get Selina to safety, the feline learns that Two-Face had removed the SD card from the camera and looks down to see him swallowing it. Infuriated, Catwoman breaks free of Batman's hold to attack Dent, only to be arrested as well, while Batman escapes the facility knowing that there is nothing further he can do. While Strange is satisfied with Dent and Selina's capture, he is nonetheless disappointed that Batman has escaped him yet again. He has his guards bring in Two-Face so that he can interrogate him personally while he increases TYGER patrols throughout the city to locate Batman.

Upon his incarceration to the prison, Two-Face became a rising gang leader in the war for Arkham City, and immediately took over the Solomon Wayne Courthouse in Park Row as his base of operations, and locked Calendar Man in a cell beneath the courthouse. To gain power and respect in Arkham, Dent kidnapped the Joker and prepared for a "trial" to be held against Joker, who he blamed to be the entire reason there ever was an Arkham City

Inviting the Penguin, Bane, Ratcatcher, Poison Ivy, Sickle, Zsasz, Riddler, Mad Hatter, the Carpenter, The Ventriloquist, Black Mask and Deadshot to be apart of the jury and Harley Quinn as Joker's lawyer, nearly every inmate in Arkham attended the court, leaving the streets abandoned and Batman suspicious of the inactivity in the facility. After Joker was proclaimed guilty and sentenced to death, Batman arrived and the entire court turned to chaos, allowing Joker and Quinn to escape with their gang, and Batman to slip away from the fight, where he met with Catwoman on the rooftops of Park Row.

Batman: Arkham City
Once Dent is brought to him, Strange sees him as a great, potential ally as his past public admiration and political prowess would serve Strange's plans and strengthen his hold over the city, though he would need to be cured first. Seeking to break Dent's addiction to his coin, he has his guards take it off his person while Strange replaces it with a coin of his own to ensure that Dent cooperates and answers his questions regarding his past. When Dent learns of Strange's deception, Strange has him released into Arkham City without his coin in hopes that he will learn to become independent of his iconic item. At first, Dent seems to function well enough to form his own gang and a headquarters within the Solomon Wayne Courthouse, locking up Calendar Man, who used the structure to kill others on holidays, in one of the court's holding cells, encouraging Strange into thinking that Dent may be able to be cured after all.

Once Dent is brought back to him, Strange puts one final contingency manipulation into effect and begins to add fuel to Dent's hatred of Bruce Wayne, whom Dent sees as nothing more than a spoiled rich boy, in preparation towards Wayne's inevitable incarceration in his facility. Strange then legitimately reaches out to Dent and gives him a choice; he will throw his coin in the air and if Dent does not catch it, then Strange would do all that he can in his power to cure him and make him the man he once was. However, if Dent does catch it, then Strange would let him loose in Arkham City and inform him of what Catwoman is doing that very second. After Strange throws the coin in the air, Dent catches it, much to Strange's disappointment and annoyance, but lets Dent know of Catwoman's impending theft of his safe.

Strange then lets Two-Face go, knowing that Dent is too far gone to be cured and serve as a useful ally, and catch Catwoman, hoping to dispose of the cat burglar so that she can no longer interfere with his plans. Soon after, Two-Face catches Catwoman just as she steals the SD card and holds her prisoner in the court house. Two-Face would soon be able to build up his forces until he is seen as one of the leading powers within the massive prison and would eventually seize complete control over the Park Row section of Arkham City to direct his affairs from. Having established himself as one of the leading crime figures in the lawless region and captured Catwoman, Two-Face intends the execute the feline thief to showcase his might and recruit others for his thriving gang. He believes that this will gain him the respect that he deserves among the gangs of the city and will make him a well placed rival to both Joker and Penguin. His ultimate plans are to recruit half of the city's populace to his cause and to slaughter the other half.

Remembering his past, Two-Face decides to flip his coin to determine whether he should give Catwoman a trial (heads up) or pronounce summary judgment (tails up) against her. His coin lands heads up meaning she gets a trial. Batman reaches the courthouse after hearing TYGER radio chatter that it would happen, and observes part of the trial, taking out armed guards and observing Catwoman tied up above a tub of the same type of acid that made Harvey into Two-Face, right before he pounces on the trial. Harvey fires wildly into the fray as his men fight the Batman and, when the Dark Knight defeats them all, Harvey quickly shoots Batman in the chest.

Two-Face then turns to Catwoman and flips his coin a second time to decide her fate; this time it lands bad side up and he raises his gun to shoot her. Catwoman manages to knock him down and frees herself from the gallows above the acid vat, scratching his face's good side in the process. Two-Face goes to kill her again with a second gun, but Batman stops him and ties him above the acid, after which Catwoman kicks Two-Face in the groin after sarcastically asking "how's it hanging Harv?", and retrieving the PDA she earlier attempted to steal. Two-Face vows revenge and is later released from his confinement by his gang.

Eventually, the tide in the gang war changes dramatically when Batman subdues Penguin and defeats most of his forces. Two-Face immediately takes advantage of this new tide and has his forces seize complete control over Penguin's territory and claim the museum as their own. He succeeds, slaughtering any of Penguin's followers who resist, converts the museum into his new base of operations, and claims all the goods, loot, and weaponry inside as his own. With a large portion of Arkham City his, Two-Face begins moving his own supplies and weaponry from the Solomon Wayne Courthouse to his new base and turns his attention to murdering Catwoman once again.

As he makes his plans however, he hears Strange announce Mayor Quincy Sharp's impending incarceration in Arkham City. Remembering Sharp from Arkham Asylum when he was Warden, Two-Face sends a handful of his men to abduct the mayor as soon as he is processed and take him to the museum so that he may kill him in retribution for the "treatments" Sharp administered on him to cure his illness.

However, Batman subdues all of Dent's men before they can capture Sharp and rescues him, leaving Two-Face to refocus his concentration on securing his position in the gang wars, now between only him and The Joker. While Two-Face and his forces were more than a formidable opponent, Joker gains the upper hand when he retrieves TYGER weapons and proceeds to leave a path of death and destruction throughout Arkham City and conquers most of it. Before Two-Face could act, Hugo Strange enacts Protocol 10, the systematic destruction of the entire prison city and inmate population through missile attacks. Hundreds of inmates are instantly slaughtered in a rainfall of death and destruction, including many in Two-Face's gang. Two-Face is able to find a secure location to remain hidden and safe while Batman defeats Strange and neutralizes all TYGER forces stops Protocol 10.

After the destructive ramifications of Protocol 10 and Hugo Strange's death, Joker's crew, most of which survived by hiding in the sewer tunnels and subway system, take over the rest of Arkham City as Joker makes the Monarch Theater into an arena for his final showdown with the Dark Knight. While most of Two-Face's gang believe that they have lost the gang war, Joker is defeated by Batman and finally succumbs to his Titan illness. As Batman grimly carries Joker's corpse out of the Theater and Arkham City, Two-Face's gang is able to resume their control over their territory, though Joker's gang would still maintain hold over a large portion of the city as well.

Planning one, final massacre against Joker's remaining forces, Two-Face also sets himself out after Catwoman, who was previously spending her time in the prison compound attempting to break into the Arkham City Confiscated Items Vault. While Catwoman was on her quest, Two-Face has his gang rig her apartment to blow with bombs and steal her loot.

Taking the loot back to Penguin's museum, Two-Face puts his army on patrol in case Catwoman was not killed in the explosion, as he prepares all weapons and ammunition for his last attack and siege on Arkham City. Two-Face himself takes a few men and holes up in the museum's armory, knowing Catwoman would come back for her loot. True to his prediction, Catwoman reemerges and systematically takes out Two-Face's men and eventually defeats him a second time. Two-Face would get one last laugh on the feline however when he reveals that he only kept half of her loot and gave the rest away to various members of his gang, at which point a frustrated Catwoman responds by knocking him out cold.

After being humiliated by Catwoman yet again, Two-Face goes into hiding and loses the confidence of many of his men, leaving his gang's future questionable. However, Two-Face's rage and vendetta against Catwoman would only be amplified further after his second defeat at her hands. Before retreating into the shadows, Two-Face leaves a threatening message on Catwoman's apartment, "Catwoman Must Die!!!"; implying that their vendetta is far from finished and has only gotten more personal, possibly foreshadowing events yet to come.