Natalie Figueroa

Living... as a free woman, thank God. The women she works with aren’t as lucky ­– she works at Litchfield Penitentiary, a women’s prison in upstate New York.

Profession... executive assistant to the warden in charge of helping the prisoners with lady-specific problems. But when one raises her hand to ask a question during orientation, she says, “Today I’m only here as a formality,” and leaves. She does everything she can to spend her time elsewhere. As far as she’s concerned, a second there cleaning up yet another mess the warden made is a second she could be spent doing literally anything else.

Interests… stopping any and all nonsense in Litchfield. The prison counselor calls an inmate’s family? She vows to destroy him. He wants to complain to her? She says he’s better off going to therapy.

Challenge... avoiding getting caught. Figueroa has been embezzling money from the prison for years, but now Larry Bloom, a fiancé of an inmate, is bringing attention to Litchfield through his column about his unique long-distance relationship. If she gets caught, she might have to join the inmates she’s been bossing around.                                                                                             

Personality... tough, no-nonsense and, frankly, pretty scary. As one of the few female prison administrators, she’s had to develop a hardened attitude. Don’t mess with Figueroa – her biggest interest will soon become ruining your life.