Secret Agent Man
Arthur Bailey
Technically a Loyalist, Arthur Bailey is the head of the Order of Shadows. Not much is known about his early life, but it is believed that he is descended from the Duke of Old Gillikin. He first came to the attention of the Order in the War and rose quickly up the ranks of the Order. Alongside the Mystic Man, he was considered one of Queen Dorothy IX's greatest advisors.
When her daughter, Queen Lavender, took over, she found Mr Bailey's secretive ways repulsive and allowed the relationship to fade. Bailey accepted this without ill feeling, knowing that his unique services will be called upon again.
When the coup took hold, Bailey didn't wait for the Queen to request his assistance. Though it is not clear how he knew, he recognised that DG's death was a temporary one and was aware of Her Majesty's plan to send her to the Other Side. It is likely he had spies within the palace and was able to connect their testimony with Lavender's sudden greying.
He worked to shore up The Plan. First he had his spies with in Azkadellia's forces proclaim that the sudden greying was due to the loss of the proper heir to the throne, playing into Azkadellia's paranoia. Then his attention turned to his daughter, Adora.
Relationship with his daughter
Bailey's relationship with his daughter is practically non-existent. Due to his status as head of the Order, he never admitted that she was his, instead having her and her mother, Anthea Smith, live in the servant's quarters. Her mother married the gardener, Theodore (Teddy) Burke, and it was this man, in her early years, that Adora considered her father.
Bailey was a commanding presence within her life, sponsoring her to go to the best schools and making sure she pushed herself beyond limits set for her by her teachers. In actual fact, he was grooming her to join the Order in his footsteps. His proudest day, though he did not care to share this with his daughter, was the day she became a fully fledged member.
Bailey took her in as his own personal protegée and Adora flourished in her work. She and the others chosen became known within the Order as Bailey's Bunch, enjoying his favour and the 'plum' assignments. This was the height of their relationship.
It was in one of these assignments that she met Wyatt Cain, though the man had no clue of her true purpose. He was investigating the bomb that Adora was ordered to set. No one was killed but several important documents were destroyed. Cain's investigation proved inconclusive, fortunately for her.
The two began to date, despite Bailey's 'reservations that she would lose her objectivity'. He considered the relationship dangerous, not only for the information that Adora had, but for her career. Adora resented the interference in her life and once she found she was pregnant, left the Order, never to return.
Even the birth of Jeb, his only grandson, was not enough for Bailey to forgive his daughter and he proceeded to use them in his plans to safeguard the monarchy, even threatening Jeb to get her to cooperate. As a result, Adora became a spy against the resistance to gain the Sorceress' trust, claiming the safety of her son as her reason. As Bailey predicted, the Sorceress eventually betrayed Adora and sent Longcoats to her home.
Bailey paid off the Longcoats that accompanied Zero with instructions to leave her and the boy alive. Zero, tortured by the idea that Cain burned his sister to death, decided to encase the man who he had thought of as 'honourable' in an Iron Suit and ordered the other Longcoats to take Adora and Jeb away.
Both were soon let go, but separately. Adora was told that Jeb was dead, while Bailey arranged for a nurture-bot, created to look and act identically to Adora to take care of his grandson.
As he predicted, Adora was enraged by the loss of her entire family and returned to the Order. Citing lack of impartiality, which Adora had to admit to, Bailey exiled her to the nearby Kingdom of Ev, in case they should decide to take advantage of the Outer Zone's temporary weakness.
Meanwhile Robo-Adora took care of her son, teaching him all he'd need to survive in the resistance. Her efforts came to an abrupt end after challenging Zero about his sister and he snapped her neck. Bailey's desire that his grandson join the resistance was later realised when he was released by Zero's sister, who was actually alive.
The Headcase
It is implied that Ambrose was purposely led near to the Cain household, though how he knew that DG would eventually end up meeting the headcased advisor is unknown.
Post Series
Apparently retired, Bailey resurfaced when Cain, unaware of their previous history, looked to him to testify at Zero's trial, believing he had evidence of Zero's mental instability and culpability in the death of his father. It turned out to have been his sister that was responsible for the death, after the man enraged her by making Zero take her punishment.