Jacob Rainwood is a member of the Rainwood family as well as the Chief Overseer of The Order. According to the Order's 1985 East Coast Assembly Manifest, he has a lazy eye.

In 1985, at age 27, he was the Overseer of The Order's New Jersey Chapter. Some time after this he gained the position of Chief Overseer, which had previously been held by his father, Lawrence, and passed on the role of New Jersey Chapter Overseer to another member. No public records of Jacob Rainwood's presence in the United States exist, not even a birth certificate, although it is known that he is within the country or is otherwise being impersonated by another individual. Matt Sharky, a former employee of his, has claimed to personally know the man and has referred to him as being a good person, as Jacob had paid Matt's rent and gone to lunch with him even after no longer employing him.

Jacob's followers are willing to go to extreme lengths to hide information on the conspiracy surrounding his father's death, even shooting at the two Harbingers they are forbidden to kill.