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Desmond "Desi" Piscatella is the primary antagonist of seasons 4 and 5 of the Netflix series Orange is the New Black. He is a sadistic prison officer, who is appointed as head guard of Litchfield Women's Penitentiary at the start of season 4, and rules the prison with an iron fist.
He was portrayed by Brad William Henke.
Early in life, Piscatella was sent to what he called a "pray the gay away camp" by his fundamentalist Christian parents. Though the experience did nothing to alter his sexual preferences, he pretended that it had in order to keep up appearances, and had a number of fake girlfriends during his time at high school. Deep down, however, the experience left him deeply cynical and mistrustful of other people.
After serving in the military, Piscatella took a job at a men's prison, where he began an illicit relationship with one of the prisoners. Eventually, word spread out that Piscatella was giving the prisoner preferential treatment and illicit gifts, resulting in the other inmates making an attempt on his lover's life. Though the attempt was ultimately unsuccessful, Piscatella and another guard identified the ringleader and punished him by tying him to a shower and leaving him to have boiling water sprayed on him for long enough to result in fatal burns. With the prisoner dead, and the other guard refusing to openly testify against Piscatella, he was quietly let go from the prison and moved into working at women's prisons.
Following the walkout of most of Litchfield's guards in protest of pay cuts, Piscatella was brought in to help quell a mass-escape of the inmates, and subsequently appointed as head guard at the prison. In order to help with the staffing shortage, Piscatella recommended recruiting military veterans, as the federal government would cover a large chunk of their salary. However, the guards that Piscatella recruited were by and in large incompetent and sadistic, which Piscatella was all too happy to ignore due to his considering prisoners of either sex to be essentially subhuman and deserving of any punishment they got. His already-poor treatment of the inmates grew much worse after the dead body of a guard (who, unbeknownst to him, was not one of his hires or even a legitimate guard, but rather an assassin sent to eliminate inmate Alex Vause) was dug up in the prison's garden, causing him to go on the warpath in an attempt to find the culprit. He began handing out punishments out of spite, recommending sentence extensions for minor infractions, and even mentally torturing inmate Galina "Red" Reznikov, who he mistakenly suspected of being the culprit.
Matters soon came to a head when the mentally unbalanced guard Thomas Humphrey tried to have inmates Suzanne Warren and Maureen Kukidio murder each other in a bloodsport game (resulting in the latter being badly injured), leading to warden Joe Caputo attempting to fire Piscatella, but the other guards closed ranks and refused to implicate Humphrey as being involved. However, a mass-demonstration by the prisoners against Piscatella the following day ended up resulting in another guard, Baxter Bayley, inadvertently asphyxiating inmate Poussey Washington. Despite Bayley's hiring predating that of Piscatella, this gave Caputo the excuse that he needed to finally fire him.
A few days later, a full-scale riot broke out over Washington's death, with the entire prison staff being held hostage. Still feeling some sense of duty to his former colleagues, Piscatella went to the prison and asked to help out, only to be informed that even if Caputo hadn't fired him, he had no authority to get involved in the situation. The increasingly unhinged Piscatella became convinced that Red was the instigator of the riot (which in reality was Washington's friend Tasha "Taystee" Jefferson), and on hearing that Humphrey had been shot and severely wounded early in the riot, stole some SWAT gear and broke into the prison with the express goal of capturing and torturing Red, while forcing her closest friends to watch.
While he was torturing Red, Vause, who was among the prisoners he had captured, escaped her bonds and tried to attack him, to which he responded by breaking her arm. Unbeknownst to him, however, another set of inmates were watching from a hidden passageway and recorded the incident on a stolen smartphone, before luring him into a trap, knocking him out and tying him up. They then uploaded the clip to YouTube, proving once and for all Piscatella's brutal approach to his job.
The revelation of Piscatella's misdeeds forced the state to offer much-improved conditions for all prisoners in exchange for the hostages to be released, but Taystee messed everything up by refusing the offer on the grounds that she was only interested in a guarantee that Bayley be tried and convicted for his part in Washington's death, even over Caputo's protests that this was simply impossible to guarantee. The state terminated negotiations on the spot and sent in the SWAT teams to end the riot at any cost, resulting in several inmates being hurt badly. On seeing that the situation had ultimately ended in failure, both Taystee and then Red threatened to murder Piscatella, but were unable to go through with it, with Red ultimately deciding to release him, deciding that she would get better revenge in knowing that Piscatella would at the very least have to live in disgrace with his misdeeds now public, and hopefully would be jailed for his actions. Ultimately, however, neither ended up being the case; when Piscatella attempted to escape, an overzealous and contumacious SWAT officer shot him in the head with a pepper-spray bullet, killing him instantly. The SWAT officers subsequently dumped Piscatella's body where the prisoners had been keeping him hostage, hoping to make it look as though they had executed him before they could be re-captured.
Though Piscatella was usually quite praiseworthy and affable to civilians and other prison staffers, and fiercely loyal to the guards under his command, his sadistic side quickly became apparent when dealing with prisoners, whom he would treat harshly for any minor misdeed, or even if he simply suspected them of wrongdoing.