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Desmond "Desi" Piscatella was the Captain of the Guards at Litchfield Penitentiary and the overall secondary antagonist of the series. He serves as the main antagonist of Season Four and Season Five and a minor posthumous antagonist in Season Six. He is portrayed by Brad William Henke.
A commanding and very authoritarian man, Piscatella enjoyed expressing his power over inmates and showed no fear in exercising it. Despite priding himself on his law authoritarian presence and holding the security to a high standard, he is ultimately shown to be quite poor at his job, not only allowing his staff to become abusive and sloppy, but for the inmates' safety to nosedive significantly. Piscatella himself is shown to be uncaring about the law, going to extremes to cover up his mistakes. He was also willing to degrade and abuse inmates to make an example of those defying his staff.
When things began to grow out of control, Piscatella's personality turned sociopathic, with him going as far as to kidnap and torture inmates in Litchfield during the riot. In the end, he is shown to be empathetic and moved by Red's actions, but his redemption is cut short when he is killed by one of the CERT officers.
Towering over the inmates at 6'4", Piscatella's height, along with his large frame gives him an intimidating appearance. In Season 4, Piscatella sported a large beard, perhaps an allusion to his homosexuality. When Season 5's Litchfield Riot began, however, he shaved his beard, explaining the decision as giving the inmates 'less to pull on.' Piscatella's hair and beard are both a brown, sandy color.
For a list of episodes featuring Piscatella's flashbacks, see here.
Piscatella mentions that his mother sent him to a 'gay conversion camp' while explaining that people don't change.
Before coming to Litchfield, Piscatella originally worked at a men's high-security facility. He had a relationship with a male inmate named Wes Driscoll, which was discovered by one of the other inmates, Miguel Rosado. Driscoll was later beaten bloody and raped by a group of inmates. As punishment, Piscatella handcuffed Rosado to a shower and turned the hot water on. Normally, the guards would turn the shower off when the inmate started screaming, but Piscatella kept it on longer than usual. Despite the incessant screaming of Rosado, Piscatella allowed the shower to run and, as a result, scalded him to death ("The Reverse Midas Touch"), echoing the real-life torture and death of Darren Rainey in 2012. The death was covered up and Piscatella was transferred to Litchfield, a minimum-security women's prison.
In "The Animals", Piscatella's brutality while trying to gain control of the protesting inmates leads to actions that cause the death of Poussey. He lacks respect for demands made by Warden Caputo to keep his unstable guards under control, and he threatens Caputo with a whole-staff walk out if one of his guards is put on suspension.
Piscatella tries to gain authority when there is a prison riot, only to be rebuked by his higher-ups numerous times. Inside the prison, Red and Blanca are reading through guard files kept in his office and uncover Piscatella's file, they further read into why he was transferred, before finding a document explaining that he had murdered an inmate prior to being transferred to Litchfield. Posing as Humphrey, they text him, asking him to come inside and help "him" so that they can attempt to fight him. When the flaw in the plan is pointed out, Lorna tries to undo it, but he's already decided to enter the prison.
Once inside, he begins capturing members of Red's "family" one by one, and then finally, Red herself. He then attempts to humiliate Red in front of the others by cutting her hair off. Alex manages to free her arms and attempted to stab him with a pair of scissors which had fallen to the ground, Piscatella forces her down, breaking her arm in the process. Piscatella is unaware that the closet connects to the pool area, where Frieda and her friends had been hiding out, Gina hearing the screams initially went up to investigate, filming Piscatella in the process.
Gina, Frieda, and the others create a plan and lure him away from Red's family. Frieda shoots him with a poisoned dart, knocking him unconscious. They tie him up so he's unable to leave or hurt them any further. Red suggests torturing him as revenge, but the idea is voted down. When Taystee enters the room, however, she grabs a gun which she holds to his head. He tries to reason with her, telling her that seeking revenge will not help, showing a glimpse of sympathy in a normally cold man. Taystee collapses to the floor in tears and Red releases him on the condition that he will leave anything or anyone. At this point, they're already aware that the riot officers are looking for them.
Piscatella leaves peacefully, however as soon as he walks into the hallway, officer Natoli accidentally fired his weapon too low from the ceiling, shooting Piscatella in the head killing him instantly, the officer is berated by his superior officer afterward.
The CERT officers try to cover up Piscatella’s death by shooting his dead body in the head once more, then plotted to frame it on the inmates, most likely to avoid the paperwork. Piscatella’s death then serves to be one of the major plot lines in Season 6 and is one of the reasons for the interrogations at the Maximum Security facility.
- Unmentioned "beard" (date) - Piscatella is gay. He mentions that he took a "beard" (a woman who fronts as a guy's girlfriend in order to give him the appearance of being heterosexual) to his high school prom.
- Wes Driscoll (ex-boyfriend) - in "The Reverse Midas Touch", it is revealed that while working in a previous prison Piscatella fell for an inmate named Wes. The two continued a secret relationship, even tattooing each other's initials on their wrists until another inmate realized their relationship and he and friends beat and raped Wes. This was the inmate that Piscatella later killed. In a deleted flashback scene from that episode, Piscatella realizes that Driscoll faked his tattoo when it wipes right off after Driscoll is attacked. This explains his distrust of prisoners and their motives. It is unknown why the scene was deleted. A glimpse of the smeared tattoo is still visible in the released episode during the shower scene.
- Thomas Humphrey (friend) - A fellow CO of Piscatella.
- Lee Dixon (friend) - A fellow CO of Piscatella.
- B. Stratman (friend) - Stratman and Piscatella are shown to joke around together.
- Artesian McCullough (friend) - A fellow CO of Piscatella. Artesian turns to Piscatella for help often, especially during the peaceful protest.
- Ryder Blake (friend) - A fellow CO of Piscatella.
- Gloria Mendoza (enemy) - After being assaulted by officer Stratman, Mendoza goes to complain to Piscatella, but is simply shrugged off under the false pretenses that all of the Latina inmates are starting a gang, and wrongfully assumes Mendoza is a part of this gang.
- Joe Caputo (disliked) - Caputo seemed to be one of the only staff of Litchfield who disliked Piscatella, toward the end of Season Four, Caputo scolds Piscatella, threatening to reveal why he was transferred from maximum to minimum.
- Galina 'Red' Reznikov (enemy) - Piscatella spends hours with Red trying to gain info on CO Aydin Bayat who had recently been found dead. Red is almost detained when Healy reveals to Piscatella Lolly Whitehill confessed. Later in season 5 he ties Red up with members of her prison family and forces them to watch while he cuts off her hair and does other things to humiliate her. After Frieda poisons him she wanted to torture him but the idea was voted down.
- Tasha Jefferson - Piscatella's actions caused the death of Poussey. Also, in Season 4, he yelled at her and implied that he and her were nothing alike emphasizing that she is incarcerated and he isn't.
- Cindy Hayes - Piscatella's actions caused the death of Poussey.
- Suzanne Warren - Piscatella's actions caused the death of Poussey. He also called her a "f***ing animal" during the stand-on-table protest in the cafeteria.
- Janae Watson - Piscatella's actions caused the death of Poussey.
- Alison Abdullah - Piscatella's actions caused the death of Poussey.
- Piper Chapman - Piper and he have a mutual hatred for each other since shortly after he arrived at Litchfield. In Season Five she is among the inmates he ties up during the riot.
- Maria Ruiz
- Nicky Nichols - Nicky is one of the inmates he captures and ties up with Red in season 5.
- Blanca Flores - After trying to attack him, he captures Blanca and has her tied up with the other inmates in season 5.
- Brook Soso - Piscatella's actions caused the death of Poussey.
- Carrie "Big Boo" Black - Boo is another inmate close to Red that Piscatella kidnaps in Season Five.
- Alex Vause - Alex is one of the inmates he has tied up with Red in Season Five. After she gets her hands free and tries to attack him, he breaks her arm.
- Gina Murphy - Gina is the one who discovers Red and the others have been tied up by him. She lures him out for Frieda to poison. She is also the one who took and uploaded the video of what he did to Alex.
- Frieda Berlin - She poisons him and ties him up after finding him with Red and the others.
- Miguel Rosado - In revenge for the event with Wes, Piscatella tied Miguel in a shower stall, burning him to death with hot water.
- There is a Certificate of Completion for a course in Welding for Commercial Divers from Adler Technical Institute hanging on the wall in his office.
- He has Wes Driscoll's initials tattooed on his wrist.
- His competitive table settings are big on Pinterest.
- He is the longest lasting antagonist of the show, being the antagonist of seasons 4-5.
- "I had a beard since the tenth grade. Two, actually. The one on my face, and the one I took to prom. Yeah, I like dudes. I'll never find you adorable."
- — Piscatella to Chapman
- "You're criminals, and you deserve nothing"
- — Piscatella in "The Animals"
- "People don't change. I should know, my mom sent me to gay conversion camp."
- — Piscatella