Jessica Haskell is a character in “The Blacklist: Conspiracy”.
Jessica Haskell was the Headmistress of Vanderpont Academy.
During her career she discovered an old dungeon that was buried under the school. With the discovery of the dungeon and her desire for discipline, she became the Castigator.
As the Castigator, she would be contracted by wealthy families to abduct and discipline their children.
Reddington brought the death of Chuck Wheeler to the FBI's attention, as he recognized it was connected to the Castigator.
For most of the case the FBI thought that the Castigator was behind the kidnapping, murder, and ransom. However, it was later discovered that Haskell was only behind the kidnapping and the murder and ransom was committed by someone else who found Chuck Wheeler in the dungeon.