Naomi was married to Red before he became a criminal, during which time they had a daughter, Jennifer Reddington. After he fled, following interrogation by the authorities, she and her daughter were forced to move to Philadelphia after being forced to “give up everything” and fend for themselves. Many years later, she married Frank Hyland.
Naomi was among the very few who knew that Raymond Reddington is not the real Raymond Reddington, but an impostor who took over his identity over 30 years ago.
She was revealed to be the true target of Lord Baltimore. Milos Kirchoff had her kidnapped to a safe house, where he cut off her finger and presented it to Red, saying 'I am going to do to her what you did to my daughter.'
Throughout the episode she is seen in Milos Kirchoff's safe house. She tries to escape but fails. Just as Milos Kirchoff is about to take another body part, he gets a call from Red telling him, “It's time for us to meet.”
At the end of the episode, she is traded for the bank accounts that Red stole from Milos Kirchoff. Dembe Zuma walks her back to Red's side. Red stops her to admire her, and it is very clear how much Red cares for her. However, he stays silent and leaves her blindfold on. In the very last scene, she is seen in the back seat of a car that Dembe is driving.
Reddington goes to visit Naomi at a house in a rural area. He tells her she looks different. She replies, “Not as different as you” and slaps him.
During her temporary concealment under Red's protection, Naomi adamantly refuses to upend her life and move again. She also refuses to reveal her daughter's location. To convince her to accept his proposal, Red brings Frank Hyland to the secret cabin and reunites him with his wife.
Talking in private, Frank agrees with Naomi that they should not move, but Naomi changes her mind and tells Frank that it's the only way to keep them safe from Milos Kirchoff. Obviously suspicious about his wife's past involvement with Red, Frank still maintains that it would be better to remain in Philadelphia. Naomi gives in, not wanting to upset her husband further, and they both tell Red that they want to stay.
However, not all is as it seems. In reality, some of Frank's refusal to move is partly due to Monica Lyons, whom he is having an affair with. Red learns this and sends Vargas to deal with the woman, who is threatened to stay away from Frank. Afterwards, Red takes Frank aside while Naomi is sleeping to discuss the matter, leading him to a road outside the cabin. There, Frank is shown Monica's dog and is appalled, thinking Red killed her. Red assures him that he didn't, but warns him that if he doesn't keep Naomi happy, there may be fatal repercussions.
Naomi meets Elizabeth Keen and they discuss Red. Before Naomi leaves with Frank, Red asks her again for Jennifer's whereabouts. She admits that she and Jennifer lost contact after she remarried.
After Red meets Jennifer again, she takes him to Naomi's grave and reveals that she was murdered, shot twice coming out of her apartment. Red admits that he doesn't know who did it or even that she was dead, and Jennifer thinks that it was one of Red's enemies. She tells him that Naomi cut off contact with her to protect her, as she knew that one day he would come looking for his daughter and she couldn't risk him finding her. Jennifer didn't even know her mother was dead for over a year. Eventually, Frank tracked her down and told her. Jennifer leaves Red at Naomi's grave to give a long-overdue apology for his actions.
While Liz is discussing all the people who have died to hide the secret of the man who took on the identity of Raymond Reddington, a shot of Naomi's grave is shown.