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Jai Wilcox was a second-generation CIA officer. His father was formerly the head of the CIA before Arthur Campbell. Because of this, Jai seemed to have issues relating to people in the workplace. He was encouraged by Joan and Arthur to befriend Annie to get information about Ben Mercer from her. Jai served as the head of the CIA's Office of Special Projects, a unit mandated to "interface amongst the various directorates and help exploit efficiency opportunities to minimize bureaucracy."
Jai Wilcox followed in the footsteps of his father, Henry Wilcox, when he joined the CIA, but he has spent most of his life trying to distance himself from the notorious legacy of the man who had been the Director of Clandestine Services at the CIA for ten years before retiring. 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 Henry eventually left her for a younger woman. Jai bears the classic features of his mother's Indian heritage, but on his father's side of the family he is third generation DC. He graduated from Yale and was ranked a Junior National squash player, but when he entered the CIA, he spent five years overseas and never did a rotation stateside, perhaps to put some distance between himself and his father. While overseas, Jai was assigned as Ben Mercer's handler in Sri Lanka. For a time, he thought he knew Ben well, but he felt betrayed when Ben eluded him and went rogue.
Two years later, Jai was stationed in London when Arthur Campbell, the new DCS, personally requested that he return to Langley. Arthur explained that Jai would be a key part of the new transparency initiative at the CIA, but Jai had another role to play. Arthur knew that Ben Mercer had had a relationship with Annie Walker in Sri Lanka, and in an attempt to draw out the rogue agent, he arranged for Annie to be called up to Langley before her training was completed, and he instructed Jai to get close to her to gain any critical information that might lead them to Ben. To accomplish this, Arthur transferred Jai from the office of the DCS to the Domestic Protection Division to act as a special liaison for new initiatives, but Joan Campbell, the head of the DPD, was not at all pleased to learn that her husband had installed Jai in her division without consulting her. Although she offered Jai a pleasant welcome, she viewed the arrival of "CIA royalty" in her division with suspicion, believing that he was there to spy on either Annie or herself, and she did not appreciate Jai's attempt to second guess one of her decisions, reminding him firmly that while she couldn't control his placement in her division, her decisions about her officers are always hers alone, and always final. Jai attempted to reassure Joan that he was merely a utility infielder, someone she could count on to support her in any way she needed. Jai is no stranger to the suspicion and mistrust of those who identify him with his father, and he remains extraordinarily diplomatic and gracious, even in the face of direct insults. He and Auggie Anderson had known each other before his arrival at the DPD, and although Jai greeted Auggie as "my friend," Auggie wondered aloud when they had become friends, and he referred to Jai as an interloper in Joan's division when he introduced him to Annie as "the embodiment of 'the man,' and I mean that in a slightly pejorative way." Their differences have not interfered with their ability to work together, however, and Joan's initial coolness toward Jai has warmed gradually as she has begun to trust his loyalty to her and her division.
Jai's closest relationship at the DPD has been with Annie, although the line has not always been clear between his assignment to get close to her and his genuine feelings toward her. Jai's initial report to Arthur was that Annie was smart and intuitive. When he approached her with an invitation for drinks at Allen's Tavern after work, his smooth and confident approach left Annie a little off balance as she wondered if the invitation was meant to be a date. Still, she found herself attracted by Jai's charm and good looks. She responded positively to his attentions, and she made it a point of learning a bit about him, admitting that a copy of his file "may" have gone around the female operatives when he first arrived, and that she knew of his preference for lattes because "baristas talk." Jai was flattered by her interest and has grown to admire her abilities. When an FBI agent expected Annie to fetch coffee during a briefing, she rose to oblige, but Jai discreetly placed his hand on her shoulder and guided her back to her seat, clearly delivering the message that she is to be respected as an agent and an equal. As Jai and Annie worked together on missions, the conversations between them became more comfortable and the flirting became more apparent. Joan has noted the personal interactions between Jai and Annie with some suspicion, and she attempted to delicately caution Annie that workplace romance is always complicated, no matter how common it is. When at last Jai and Annie had their first date, it was a deliberately casual affair, a barbeque at Annie's home with her sister Danielle and her brother-in-law Michael. Keeping their CIA covers intact, Jai told Annie's family that he was just a suit-and-tie man for the State Department and that he and Annie had met at a coffee shop near her job. Danielle, who had been anxious for Annie to find someone new since the love she had lost in Sri Lanka, highly approved of Jai, enthusiastically whispering later to Annie that "He's, like, the George Clooney of wherever he's from!" Jai, however, was willing to take things slowly, understanding that Annie was still a little gun-shy, admitting that he had been there before, and promising that he would still be around if she needed to take her time. However, the trust between them began to shatter as memories began flooding back to Annie and she started to recall that she had seen Jai before they had met at the DPD, that he had in fact been with Ben in Sri Lanka. At first confused, she felt betrayed when at last she had confirmation that Jai had been Ben's handler. She confronted Jai, demanding to know why he had kept his association with Ben a secret, but she was unsatisfied with his answer, that he had wanted to explain but so much was classified. The relationship between Jai and Annie was further put to the test when Annie accompanied Ben back to Sri Lanka, and Jai, no longer trusting Ben to keep Annie safe, followed in an unsanctioned mission to provide backup.
Jai's role at the DPD has varied. He has been involved in the gathering and analyzing of information, and he has participated in briefings to plan and monitor missions in the field. He has also run point on certain operations from the DPD, such as the mission to target the leak of information from within the Senate Intelligence Committee. Despite any concerns Joan might have for the relationship between Jai and Annie, she has not hesitated to assign Jai to work with Annie, both as a partner on missions and as backup. Jai and Annie accompanied Christopher McAuley to New York to capture Hasaan Waleed, and Jai recognized Ben Mercer at the scene of Waleed's assassination, although he was not able to take him into custody. He partnered with Annie as backup for Auggie when Auggie returned to the field to negotiate with Natasha Petrovna, and he acted as backup when Annie and Ashley Briggs were targeted by an Indonesian assassin and when Russ Hilburn's men threatened to kill Annie at the marina. During Annie's deep cover mission to London, Jai and Agent Roach provided backup for Annie as she infiltrated Patricia Ridley's smuggling ring. Unlike Annie, Jai does carry a gun, and he has demonstrated skill and accuracy when he has been called upon to fire it. When Annie was taken into custody by the FBI after the shooting incident at the Bramble's Auction House, Jai and Auggie coordinated their efforts to uncover the truth about Annie's activities. Driving to Georgetown in his gray metallic BMW 535i, he broke into Annie's home, searched her room, and discovered the pictures of Ben in her scrapbook, which put him in the delicate position of lying to Auggie about his knowledge of Ben Mercer, while protecting Annie, and remaining loyal to Joan.
Jai has proven himself to be an exceptional and loyal operative. Unlike Annie, who often follows her instinct, Jai tends to follow logic and reason. He finds it more difficult to trust, perhaps because of the conflict with his own father or because of the sense of betrayal he felt when his partner Ben went rogue. In Sri Lanka, Annie was certain that Ben could be trusted, but Jai was prepared to take Ben down if necessary. Similarly, Annie was convinced that Auggie could be trusted when he and Natasha escaped toward Canada, but Jai was not so sure, admitting, "I do like Auggie, but if I put my personal feelings ahead of analysis, then I'm not doing my job." Yet despite his doubt in the absence of proof, he respects Annie's ability to trust on faith. It may be his reliance on analysis over emotion that has helped Jai cope with the negative reaction he often faces. When Joan questioned his motive for joining her division, he politely offered his support. When Auggie described Jai's father as "The Prince of Darkness," Jai smiled and suggested his favorite alternative, "Satan's Little Helper." When McAuley declared to his face that Henry Wilcox is an asshole and deserves to rot in prison, Jai offered no argument, perhaps because it wasn't the time to pick a fight with an operative, or perhaps a part of him didn't entirely disagree.
Jai's relationship with his father has been a difficult one. He recognizes the negative light in which others see Henry Wilcox, and he tries to separate himself from his shadow, yet through the years he himself has endured the criticisms of his father as well. 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, Henry seems to relish the opportunity to point out that his son has not quite lived up to his expectations. When Annie joined Henry and Jai for drinks at Allen's Tavern, Henry directed his remarks toward Jai as he acknowledged that even his son doesn't approve of him and as he spoke of those agents who don't belong in the CIA because they don't have the stomach to live with getting down in the mud. Henry did not approve of Jai's decision to come back from London at the request of Arthur Campbell, and he made no secret of the fact that his opinion was not career advice but rather criticism. The two rarely converse or spend time together, so it was unexpected when Jai paid a visit to Henry at his magnificent home 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. In a remark intended to compare Jai to his former partner, Henry declared that two kinds of people succeed at the CIA, those who are very good at taking orders and those who cannot take orders, and Ben is extraordinary because he is an example of the latter. With a smile, Henry offered a warning to look out for himself and to take initiative because there is much more that Jai doesn't know, but his words only made Jai more determined than ever to sever the ties with his father and to be the kind of person his father is not.
In the season 3 premiere Jai is killed when his car blows up as he starts it up after talking to Annie.