Henry Wilcox had been the Director of Clandestine Services at the CIA for ten years. Condescending and manipulative, he had earned a reputation for living in the shadows, and he ran the Agency with very little transparency. He believes that in order to take down the bad guys, in order for good to win over evil, it is necessary to get down in the mud, and that all operatives at the Agency are in the mud, even if they don't want to admit it. He notes that many agents can't live with that, and many leave early because of it, but those who succeed at the CIA are either those who are very good at taking orders, or those who cannot take orders at all. He arrogantly relishes his reputation for cloak and dagger, and he acknowledges with some pleasure that everyone disapproves of him, even his own son. His greatest statistic during his tenure at the CIA is that he ran more dark ops than anyone since the Cold War, and he became known affectionately by half the press as "The Prince of Darkness" or "Satan's Little Helper."

Among the dark ops begun under Henry's watch was the CIA's involvement with Hasaan Waleed. Waleed used to be an asset in Sudan, feeding information to the CIA in exchange for money and supplies. He and his bosses built their entire operation with CIA funding and support, and then they turned on the Agency. The CIA sent Vanessa Sinclair, an operative who was part of Henry Wilcox's shadowy Albion Group, to deliver a shipment of arms to Waleed, but he killed her and used the weapons that the CIA had given him to build a terrorist cell. Five years later, Henry had retired, Arthur Campbell had replaced him as the DCS, and Waleed was arriving in the US and smuggling in a shipment of weapons. The CIA coordinated with the FBI and prepared to arrest Waleed and turn him over for trial, but Henry returned from retirement to warn Arthur that there are some stories that it will do no one any good to have out in the open. As Henry filled in the background of Waleed's history with the CIA, Arthur realized that even though Henry had begun the operation, Arthur had been with the Agency at the time, and his own career would never survive the scrutiny if a trial brought to light the fact that the CIA had armed a terrorist cell. Arthur was forced to heed Henry's warning and cut the FBI out of the loop, intending to take Waleed into CIA custody and turn him as an asset once again. The mission didn't end as Arthur had expected, however, when Ben Mercer assassinated Waleed upon his arrival in the US, and the weapons were confiscated by the CIA. Ben had gone rogue two years before and no longer followed chain of command, but he is an agent well known to Henry Wilcox, an agent whom Henry describes as extraordinary because he is among those who cannot take orders.

Both Arthur and Joan Campbell had served under Henry when he was the DCS, and neither views him in a positive light. Arthur's conversations with Henry are icy and barely civil, and while Arthur admitted to Henry that "I may not like you, but I respect your talent," Henry replied, "I like you, Arthur, but I don't respect your talent at all." Joan considers Henry "a dangerous old windbag angling to come out of retirement," and neither has welcomed his occasional visits to the CIA to tell them what they are doing wrong. When the decision was made to dedicate the brand new CIA Ops Center to the former DCS, Henry returned to bask in the glow of the ceremony, and Auggie Anderson voiced his contempt at dedicating the center to someone with so much dirt on his hands. In the hypocrisy of praising a man he does not admire, Arthur spoke during the ceremony of his "friend and predecessor" and of the incalculable debt owed to those who have gone before and the pride of standing on their shoulders. When Henry next returned, he had shaved off the beard he had grown in retirement. The Director of National Intelligence had requested that he be read in on an operation involving a weapons smuggling ring with ties to Angola and the US Embassy in London, and Henry self-righteously considered the simple consultation to be a call of duty. He stressed that the priority of the mission was to get their operative inside the smuggling organization even if it meant risking the life of an employee at the Embassy, but Arthur was not prepared to sacrifice a life for a mission. Arthur stood up to Henry, overruled his decision, and ordered him to leave, making it clear that Henry was only there because he had lobbied the Director to put him there and that it was time that he grew back his retirement beard. The operation was considered a success, but Henry departed in disgust, declaring that "optimism weakens any equation" and warning that Arthur had lost a huge opportunity by choosing to save a life and blow a mission.

Arthur has not seen the last of Henry, however. Liza Hearn, a reporter for the "Washington Recorder" newspaper, has been using inside sources to publish articles that dig into dark ops and paint the CIA, and specifically Arthur Campbell, in a very negative light. Henry is confident that as an emeritus official, he is safe from prosecution, but even though Arthur has merely inherited the dark legacy of his predecessor, Henry has warned him to plug the leak or he will find himself facing an inquiry on Capitol Hill, or even jail. What Arthur doesn't know is that Henry himself is Liza Hearn's source, and he has smugly assured Liza that with his help, a Pulitzer might be within her grasp.

Henry's relationship with his son Jai is also very strained. Jai's mother is a neurosurgeon from Mumbai. She had once been Henry's asset when he was stationed in India, but her cover was blown. Henry married her, and they became the Romeo and Juliet of the Agency, but their romance became a cliché when he eventually left her for a younger woman. Jai had followed in his father's footsteps by joining the CIA, but he spent five years overseas and never did a rotation stateside, perhaps to put some distance between himself and his father. Despite the fact that Jai has distinguished himself as an excellent agent, Henry tends to exhibit a patronizing and disparaging demeanor toward his son, speaking in pleasantries while offering criticism both personally and professionally, even in public. The two rarely converse or spend time together. Henry does not approve of Jai's decision to come back from London at the personal request of Arthur Campbell, and since his return Jai has kept his distance from his father. Consequently, it was unexpected when Jai paid a visit to Henry at his magnificent home with an expansive and immaculately landscaped lawn and a patio overlooking a view of the river. Jai came seeking advice, but the only recommendation Henry would offer was to distance himself from Arthur Campbell. Jai had been Ben Mercer's handler in Sri Lanka, and he had come to suspect that Ben might have been taking orders from someone else. When he confronted his father, Henry merely smiled and evaded the question, admitting that he knew Ben very well, and implying that there is much more that Jai doesn't know. Henry repeated his warning to look out for himself and to take initiative, once again giving the impression that he is far more interested in pulling strings behind the scenes than helping his own son.

Portrayed by: Gregory Itzin

Cross Reference: Albion, Arthur Campbell, Joan Campbell, CIA, Liza Hearn, Christopher McAuley, Ben Mercer, Vanessa Sinclair, Hasaan Waleed, Jai Wilcox

Episode Reference: In the Light, I Can't Quit You, Baby, When the Levee Breaks