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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 and an anti-villain in later seasons. She can be considered the bigger bad of the first 2 Seasons being the reason for many of Litchfield's problems.
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.
It is later shown that a lot of the manipulativeness and toughness comes from her husband, Jason, who was a big part of the embezzlement scam. She has doubts about it and fears what will happen if they get caught, and her husband quickly reassures her that they won't. After the incident when she catches her husband making out with another man, she appears physically and emotionally weaker. She also, as found out by Piper and Caputo, has bulimia, an eating disorder. This is discovered when Piper finds piles of candy wrappers she had binged on in her desk drawers.
After the discovery of her husband's affair, she begins her own with Joe Caputo, casting her as a desperate woman in need of attention from another person. She proclaims that she only sees Caputo because he is a "good lay", but she seems to care for him, breaking her hard exterior.
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.
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.
Fig is later seen to be having an affair with Caputo, most likely to escape her marital problems with her husband, Jason Figueroa, who is 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 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 the inmates 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 CO Bailey would be arrested, and Taystee turns it 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.
- 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): She performs oral sex on him in Season Two. 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 planned to have sex after the riot was assumed to be resolved in season 5, but were interrupted.
- 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.
- "I'm only here as a formality."
- — Natalie Figueroa to the new inmates during orientation
- "Get some fucking therapy, man."
- — Natalie Figueroa to Sam Healy
- "Your heart bleeds the way a vagina should."
- — Natalie Figueroa to Joe Caputo
- Her vagina's name is Tracey.