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Natalie Figueroa (commonly known as Fig) is the former Executive Assistant to the Warden at Litchfield Penitentiary. She serves as the supporting antagonist/bigger bad of Season One, the secondary antagonist of Season Two (first villian being Vee) and an anti-villain in later seasons. She can be considered the reason for many of Litchfield's problems due to her actions in the first two seasons.
Figueroa comes off as incredibly confident, professional, and arrogant. She is often very mean, cold, and manipulative towards the inmates and staff, and cares more about the reputation of the prison than the welfare of the prisoners. She dresses in expensive clothing and designer shoes and drives a Mercedes convertible. It is implied that she started her job with optimism for change, but was broken by the system.
It is shown in Season 2 that a lot of her manipulativeness and toughness comes from helping her husband, Jason, embezzle money for his state senate campaign. She has doubts about what they are doing and fears what will happen if they get caught, and but Jason quickly reassures her that they won't and that what they are doing is for the greater good of the state. After a campaign event where she catches her husband making out with his campaign manager, a man, she appears physically and emotionally weaker. At the end of Season 2, Piper finds piles of candy wrappers she had binged on in her desk drawers, hinting that she has bulimia, which she confirms herself in Season 6 while talking to Joe Caputo. She is also revealed to have anorexia in Season 6.
After the discovery of her husband's affair, she begins having "hate sex" with Caputo in Season 3. She proclaims that she only sees Caputo because he is a "good lay", but as their relationship further develops, she seems to care for him. He attempts to break her hard exterior in Season 6 by asking to see the "real Natalie" and singing karaoke to her.
Fig is quite slender, and she has long light brown curly hair. She is usually seen wearing formal attire and jewelry. Tall, 6' 1" (1.85 m), she has a pleasant smile and a stern frown. Her slender figure and long face appear glamorous, but can be played as somewhat intimidating. She also uses her sex appeal by flashing her legs when she interacts with males.
As a young girl, Fig was best friends with a girl called Tracy Loomis who began puberty before her, and as a result of this, Tracy became popular because Tracy supposedly had sexual interactions with a boy named Jason. This then resulted in Fig naming her vagina after Tracy as she found Tracy and her vagina to be a "bitch".
In Changing Winds, she tells Joe Caputo that she used to be fat, which she firmly believes resulted in her not being pulled up on stage by Bruce Springsteen during the shooting of the "Dancing in the Dark" video.
In season one, Natalie is mostly shown butting heads with Joe Caputo, whom she considers to be incompetent at his job, over management of the prison. She comes across mostly as cold and condescending, but shows more humanity than some of the other prison employees when Tricia Miller dies. She also sternly lectures Sam Healy about calling Piper Chapman's fiance and telling him that she's having a lesbian affair.
In Season Two, it is revealed that at the expense of the prison, she embezzled money from the Department of Corrections by cutting funding for programs and other "luxuries". At the expense of the inmates, she covered up events that were potentially damaging to the reputation or funding of the prison. Piper Chapman, sick and tired of the clearly corrupted prison, tried along with a reporter to uncover the scam. In revenge, Fig attempted to have Piper transferred to another facility, motivating Piper to steal files from Fig's office containing incriminating evidence related to her embezzlement scam.
In "We Have Manners. We're Polite." Fig is busted by Joe Caputo who has the evidence obtained by Piper, in an attempt to buy Caputo's silence, she performs oral sex on him, but to no avail, as Caputo has already spoken to the Warden. Fig subsequently resigns as Executive Assistant to the Warden.
Natalie is living with Jason Figueroa in Albany after he wins his campaign for senate. Caputo calls Natalie when the prison is going to be shut down. He threatens to expose her and her husband to their voters, and she meets him at the prison with a business plan from MCC. She advises him to schedule a walkthrough as they were previously interested in buying the prison. She is later seen to be having an affair with Caputo, most likely to escape her marital problems with her husband, Jason Figueroa, a closeted gay man.
In "The Animals", Caputo visits Natalie's large house, where she is alone, drinking wine. Caputo asks if Natalie is drunk, and she invites him in. He declines at first, telling her that he has a girlfriend - a "weird, lying, gun-toting, manipulative, corporate girlfriend", which Fig already knew, being friends with someone named Margie at MCC. He eventually agrees to go in and "just talk". In "Toast Can't Never Be Bread Again", it is hinted that they had sex when Linda spots that Caputo has bite marks on his ear.
Figueroa is sent into the prison on behalf of the governor to negotiate the inmates' demands with Taystee in an attempt to end the riot and free the hostages. She goes in planning to dismiss most demands, but it becomes apparent that Taystee did her homework. Eventually, Caputo is brought in to help give the inmates credibility, and after pulling all-nighters, a deal is made; all of their demands will be met - besides justice for Poussey. She explains that they don't have the power to ensure that CO Bailey would be arrested, and Taystee turns their whole deal down. Later, it is assumed that she tells the officers where the old pool is so they can retrieve the ten inmates hiding down there.
Figueroa is reinstated as warden at Litchfield Max. She begins to see Caputo again, although her being warden upsets him. Their relationship develops to the point that he tells her she's his "girlfriend." She starts an unlikely working relationship with Linda Ferguson, reluctantly helping her when MCC faces a public relations nightmare after the riot. She helps Caputo figure out how to undermine MCC to try to help Taystee. After the trial, she takes care of a beat-up Caputo when he shows up at a MCC/Polycon Corrections event drunk and looking for her.
- Jason Figueroa (husband): Jason is Fig's husband. She discovers that he is gay and in love with an assistant named Gavin. However, they have remained married as he was elected to the New York State Senate.
- Joe Caputo (affair, later boyfriend): She performs oral sex on him in Season Two to try to keep him quiet about her embezzlement. In Season Three, they are shown to be having an affair. Joe gets a girlfriend in Season Four, but in the "The Animals" visits Fig's house. It is implied that they had sex after Linda spots bite marks on his ear in "Toast Can't Never Be Bread Again." They also attempted to have sex after the riot was assumed to be resolved in season 5, but were interrupted by the governor's assistant. In Season 6, they began having casual sex again, then started going on dates and eventually became an official couple.
- Tasha Jefferson (enemy) - During the riot, Fig enters to settle things. Fig and Taystee have an argument over the demands. After Fig cracks under Taystee's words, she says all demands will be met except for Bayley's arrest. Fig is kicked out, saying it will be all or nothing.
- Linda Ferguson
- "I'm only here as a formality."
- — Natalie Figueroa to the new inmates during orientation
- "This isn't a contest. You do your best because that's what you're supposed to do. Why is it so hard for you people to understand? You're like babies! "Where's my present?" "Pay attention to me!" "Give me things!" "Fix the heat!" "Build a gym!" I'm not your goddamn mommy. Grow up!"
- — Natalie Figueroa to Tasha Jefferson ("Looks Blue, Tastes Red").
- "Get some fucking therapy, man."
- — Natalie Figueroa to Sam Healy
- "A lot of men shave their balls! It doesn't mean they're gay!"
- — Natalie Figueroa to Joe Caputo about not realizing her husband was gay
- "Your heart bleeds the way a vagina should."
- — Natalie Figueroa to Joe Caputo
- "Of course there are still bad people who commit heinous crimes, and it is unfortunate one of these sickos ended up under our roof."
- — Fig delivering a statement to the public after Pornstache is arrested
- Her vagina's name is Tracey.
- She developed anorexia after Courtney Cox was pulled onstage at a concert instead of her, as she thought she was too fat to be pulled.
- She has the longest span as a recurring character, lasting for six seasons.