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Detective Hailey Upton (married Halstead) is a member of the CPD Intelligence Unit. She is the partner and wife of Detective Jay Halstead. She is portrayed by Tracy Spiridakos.

Biography

As a child, her family ran a diner in Greektown. Mr. Upton was very abusive, as he would regularly beat her mother, brothers, and herself. Despite the abuse, her mother remained at the house with her father even long after she and her siblings moved away.

When the diner was robbed in 2003, by which time she was 10, she stayed by the desk of Sergeant Trudy Platt, who was part of a Robbery-Homicide unit at the time, until it was solved, all the while worrying for the health of her father. This event, combined with the childhood abuse, inspired Hailey to become a cop, where she eventually became a member of that same Robbery-Homicide unit. She was meritoriously promoted to detective after her work on an undercover case.

She later joins Sergeant Hank Voight's Intelligence Unit and is partnered with Detective Jay Halstead.

Seasons

Season 4

Hailey is introduced during Fagin, when she crosses paths with Intelligence and tries to make it clear that they are working her case until the chief speaks in favor of Intelligence. Hailey is allowed to rejoin the case and her own dealings with the case help uncover teen robbers being given orders by a former convict who cannot himself perform the robberies due to a physical impairment. She is also surprised that she is able to take part in an interrogation with Lindsay. At the end of the episode, Hailey complimented Hank for helping one of the adolescent robbers so he can still live a life once out of jail. Impressed with her work on the case, Hank offers Hailey a spot in his unit. Taken aback by this, Hailey does not give him an answer but does consider it. He tells her symbolically to leave the door open.

In Army of One, Upton is shown entering the bullpen confirming she's taken the job. She is partnered with Erin Lindsay for her first days at Intelligence. In the episode Fork in the Road Hailey covers for Lindsay's misstep with a suspect, telling Platt that what she says in the interview won't reflect poorly on Lindsay nor the unit, thus already proving her loyalty to the team. Lindsay later chooses to accept a job offer with the FBI.

Season 5

As of Reform, Hailey is shown to be partnered with Halstead. When the teams attacks a known gang spot, she finds a young girl shot and is then shown covered in blood, visibly jarred by the situation. Later in the episode, ballistics prove that Jay was the one that shot the girl. Hailey shows compassion and support for her partner's unfortunate situation in the episode. Hailey also officially meets Antonio Dawson.

During Snitch, Hailey is furious at Adam Ruzek for punching a suspect after he insulted her. After this, a complaint is filed against Adam. Hailey is hesitant to cover for him as she's intent to be on the side of the truth, but in the end her loyalty wins out, and gets a witness to alter their statement.

In Fallen, Hailey is reunited with an old colleague Sean McGrady, who is now a sergeant for the Narcotics unit. She shows disregard toward him due to a past shaky workplace relationship. After being approached by Voight, she is forced to work with McGrady on a case. While working on their case together, she responds to a call from McGrady, and is shaken when she finds him shot. After investigating his death, Upton finds evidence to prove that McGrady actually committed suicide, and framed a local gangbanger for the death. Reluctantly she attends McGrady’s funeral and is disgusted that he was being revered as a hero. Later confronted by Voight as they leave, Hailey says that while McGrady was a good cop, he was not a good man and had little other redeeming qualities, recounting his past actions such as cheating on his wife, and actively trying to sabotage her police career. Though reluctant, Hailey is convinced by Voight to bury the evidence and to keep McGrady's name intact, in consideration for his family needing his pension.

In Care Under Fire, Hailey is unsettled about Jay's involvement in a case which could trigger his PTSD from his military service. Throughout the case she constantly questions Halstead and his actions. This is continued into Rabbit Hole, where Hailey must work against her partner for his own good. In the end, she covers for him by intimidating Camila Vega, saying she'll bury Vega if she talks about her secret relationship with Jay.

In Confidential, Hailey and Kim Burgess work together to solve a case involving a prostitution ring. Upton and Burgess butt heads on how to handle their confidential informants. One of Upton's CI's has information that can help solve the case, but Hailey decides to not use it, telling Kim that if they use the information, her CI might wind up dead. After solving the case, Hailey tells Kim that sometimes, you have to trust your gut and not the book. They leave the locker room agreeing on grabbing dinner later that weekend. Hailey also threatens to get a new partner, if Jay doesn't take therapy seriously. Because of her reaction, Jay finally goes to therapy again. Later in Chasing Monsters, Hailey asks Jay about therapy and is happy to hear that it benefits him.

In Ghosts, Intelligence unit investigates a meth dealer that Upton knows. Hailey asks Voight for permission to bring back an old undercover identity to help take down the meth ring spearheaded by a former criminal contact, Ron Booth. After reviewing the old case file, Voight asks her about Garrett Thompson, Hailey's old partner. Hailey reveals that she was under as his girlfriend. Booth never liked him and one day Garret was gone. Hailey insisted that he was killed, though the body was never recovered. Hailey asks Voight to put her under so that she can introduce Jay as a potential buyer and bust Booth. Hailey eventually gets in contact with Booth and tries to take him down. While talking about the past, Booth apologizes for what happened at a New Year's party. Jay gets curious and reaches out to Hailey's old case officer, Jeff Rafferty, to find out what really happened to his partner that day. He later confronts Hailey and asks what happened. Hailey tells him that she was trying to get information from a drunken Booth. Booth had other things in mind and tried to rape her. Hailey got away and went to the hospital after being brutally beaten. Jay questions her closeness to the case, but Hailey promises that she is okay. The next day, Hailey goes to Booth to set up a meet with Jay. Booth agrees to meet Jay and tells her the details. When Booth meets up with Jay, he asks whether Jay had slept with Hailey. Jay says no and Booth calls off the meeting. After telling Voight what happened, Voight tells the partners to shut down the undercover operation. Hailey infuriated that Booth might get away, goes behind Voight's back and decides to confront Booth one last time. Jay finds out and follows her to Booth's warehouse. After showing him the money, Booth agrees to do business finally. Jay approaches Hailey at her undercover apartment and demands an explanation. Hailey tells Jay that she needs Booth back in prison for some closure for Garrett's death. They meet Booth later and before they can exchange the money and drugs, things go sideways. Booth figures out Hailey and Jay are cops and run. Hailey goes after him and gets into an altercation. Hailey gets the upper hand and points a gun toward him demanding a confession for Garrett's murder. Jay talks Hailey out of pulling the trigger asking her to trust him. Hailey lowers her weapon and Jay arrests Booth. At the end of the episode, Jay goes to Hailey's place and shares a drink with her, even after she says she wants to be alone. After talking, Hailey reveals to Jay that she had loved Garrett.

Season 6

During New Normal, Hailey tries to get Adam to understand Antonio's side of the story pertaining the events that occurred with the previous case. While trying to solve the case, Adam brings Hailey into the middle of the quarrels with Antonio and she becomes angered with it. At the end of the episode, Hailey is one of the pallbearers at Alvin's funeral and pays tribute to her fallen comrade.

In Endings, Jay deals with the loss of his father, who dies in a building fire. While investigating the arson, Hailey tries to be there for him, but every-time she tries to get him to talk, Jay shuts her down or takes out all his anger at her, using her as his human punching bag. After Jay's near-death situation, Hailey and Adam decide to go out for drinks. At the end of Endings, continuing with Bad Boys, Hailey and Adam hook up, after an emotional day. They decide to continue seeing each other as start a relationship.

In Fathers and Sons, Hailey goes undercover and successfully infiltrates a drug deal. She has Adam pose as her rich boyfriend. When they meet the leader, things go good until Adam spots a familiar cop. Hailey noticed that Adam was nervous around him and asks about it and he tells her that the cop they saw was his father Bob Ruzek. Adam keeps the new discovery a secret and continues to solve the case, but Hailey doesn't like it and tells Adam to tell Voight about his dad or she will. Adam finally tells Voight and they figure out a plan. While trying to bring down the leader, Bob gets shot and end up in the hospital. The episode ends with Hailey meeting Adam at the hospital and being there for him.

During True or False, Intelligence investigates the brutal beating and death of an alderman’s wife. After talking to a witness, they identify the suspect as Devin Williams and bring him in. After many attempts of getting a confession by the other members, Hailey goes over the suspects background and sees a weakness. While interrogating Devin, she asks about the abuse from his childhood. She connects with the suspect, by opening up about her own abusive childhood. After finally getting a confession out of Devin, she is congratulated by Voight on her job well done. Hailey insists she made up those stories about her past when Ruzek asks her, saying that she was playing Devin. Later in the day, Jay pulls Hailey aside and shows her a credible security footage which shows that Devin was somewhere else during the murder. This proves that Devin was not the actual killer. When she goes to confront Devin about this false confession, she finds Devin dead. Jay tries to be there for her and tells her she didn't do anything wrong. The team later finds out that the Alderman was involved in the murder of his wife and arrest him. Hailey later confesses to Ruzek that the stories about her past were true. Throughout the case, her and Ruzek continue to try to keep their relationship a secret.

When a case gets personal to Halstead in Trigger, Hailey is there for him. She shows much resistance to prejudice and bias, insisting not all Muslims are terrorists and giving the benefit of the doubt to a woman hiding something under her burqa. At the end of the case, she is very supportive of her partner, listening to Jay talk about his past in the military and refusing to leave him alone with his guilt because of the "thing that works between us".

Descent and Brotherhood shows her relationship with Ruzek deepening, as she is afraid of something happening to him after he covers up a crime for his fellow team member. In the latter episode, Halstead walks in on them having a personal conversation and realizes they have a romantic relationship. Hailey apologizes for keeping it a secret from him, to which he responds that they are "always gonna be good".

In Outrage, Hailey shows to have Jay's back after someone from his past, who he despises, is involved in a case they are working. When this person is found dead, Jay is the number one suspect. Jay asks Hailey if she thinks he is involved, and she quickly says no, showing that she believes he is innocent. Once they find the real killer, Jay and Hailey have a beer at a bar talking about the day they both just had. During their conversation, Adam calls Hailey and Jay tells her she should go. Hailey agrees and leaves Jay alone at the bar.

In Ties That Bind, The team go undercover to bust guys selling guns. During a buy, things go wrong and Hailey and her fellow officer Kim Burgess are kidnapped. As the ranking officer, Upton convinces Burgess to stay put and let the team come to them. As the team searches for their friends. Burgess and Upton tries to take control of the situation, but things go wrong. Burgess manages to get away but Hailey is badly beaten in the process. The guys finally find them, and bring them home. Burgess also finds out about Hailey and Adam's relationship and they talk. They share a drink and Hailey tells Kim the reason why she hid her relationship. She tells her that in her old unit she was dating a sergeant when she was meritoriously promoted to detective. Even though she earned the promotion, everybody assumed it was because of her boyfriend. Since then she has kept her personal life private.

In Good Men, Hailey backs up Jay about a decision. When Jay later asks why she did it, Hailey responds with, "I trusted you. I've trusted you from the day I've met you. And if I was gonna follow someone blind, I'd follow you."

In Sacrifice, Hailey and Adam respond to an armed robbery. While working the case, tension grows between the couple, when Hailey made a call that Adam didn't approve. After taking advice from Platt, they realize after a tough case on which they had disagreements, that the relationship between them isn’t working. Partly because it's hard dating and working together, but Hailey also says they both know it's more than that, most likely referencing his romance with Burgess.

In Reckoning, the team try to find a way to bring down mayoral candidate Brian Kelton, but everything they do seems to lead them to a dead end. While unpacking their equipment from an earlier raid, Hailey and Jay tease each other on their possible placement once Intelligence in disbanded, in which Jay tells her that he is going you she goes, as "it's hard to find a good partner". Later in the episode, as things seems to be falling apart for Intelligence, Hailey tells Jay that everything will be ok, and that he will forget soon, as they have only been partners for a few years. Jay quickly shuts her down, and the two share a moment.

Season 7

In Doubt, as the team try to figure out who killed Kelton, Jay is placed in charge as Voight is a possible suspect. He shows to value her opinion for everything, always asking what she thinks about the situation.

Familia sees newcomer Vanessa Rojas joining the unit, and she is partnered with Hailey, who Voight appoints to assess Rojas out because he knew Hailey will be straight with him. At first Hailey is upset by this split in partnership between her and Jay, but eventually accepts it and even takes Rojas under her wing, inviting her to stay at her place.

In the three-part crossover Infection, Hailey is quarantined with a young girl, once again revealing more about the robbery that happened in her childhood. She is also concerned when Jay is held captive by a doctor who is trying to release a deadly virus on the city. Ultimately, to catch their suspect, Hailey fires the shot to distract him, resulting in his death and saving Jay's life.

Informant shows Hailey's relationship with one of her CI's, Cameron. She and Cameron go undercover to get deadly drugs off the streets and during the investigation, her CI is made by Darius Walker and she has no choice but to pull him from the case. Cameron is still persistent on helping Hailey with the case and asks her to meet up. At the location, while the are talking, Cameron is shot and killed in front of Hailey and this deeply shakes her. She is adamant to hold Darius Walker accountable for killing Cameron, but as they have no evidence against Walker, Voight decides to use Darius to try to solve their drug case. She is forced to go against her gut to protect the murderer of her CI, and in the end revealing she has difficulty carrying his death.

In Absolution, Hailey figures out that Jay has been helping out a family from a previous case and tells him that he is too close and needs to walk away before they find out who he really is. They get called into a case and at the crime scene, Jay has to leave suddenly, asking Hailey to cover for him. The next morning, Hailey tries to call him but it goes to voicemail, which worries her. After realizing that Jay is missing, she is adamant to find her partner. She starts losing hope when one of their approaches to the case falls apart, but Adam assures her that they will find him. She is extremely worried, feeling guilty about keeping his secret of what he was up to, and does everything she can to find him. They eventually track down the abandoned warehouse Jay is being kept at, and Hailey goes in alone and finds him. After seeing Hailey, Jay goes back downstairs to help free the other hostage, but gets shot instead. At the beginning of Mercy, Jay is rushed to the hospital where he has an emergency surgery performed. Hailey is shown struggling with his uncertain fate, to which Rojas reveals it’s hard for Hailey because she loves Jay. Hailey tells her "Of course I love, he's my partner." Ultimately, she is relieved to see he survived the shooting, and almost admits to him that the event made her realize her feelings for him. In 43rd and Normal, Hailey is happy when Jay is back at work even if he has to be on desk duty.

During The Devil You Know, Hailey is once again forced to work with the person who murdered her CI in Informant, Darius Walker. A dark side is shown of Hailey, as she goes to extreme lengths to get justice. She begins to cross lines and leaks information to Darius' crew that he is working for the police. Jay follows her and tries and talk her out of it, telling her that he is getting to close to the case. She insists she is fine and the next morning, Darius is found dead. Voight later tells her that he doesn't want her to become like him reminding her that he does what he does because he can and knows how to shut off his emotions.

In Center Mass, when a case gets personal for Vanessa she is there for her. Vanessa ends up shooting one of the suspects who she believed had a gun in his possession. After searching the body and finding none, Hailey comforts Vanessa and tells her to stay string and that they will find the gun.

In Intimate Violence, Hailey is seen to accompanies Jay to one of his doctor's appointments. She tells him that she talked to Voight and he wants that partnered up again. Jay agrees and they get called to an armed robbery call. Things gets personal for Hailey, as she relates to the female witness of a robbery, who is being abused by her husband. Although she has deep connections with the case, she is is able to control emotions and get the case solved. After the case is solved, she and Jay share drinks where she talks more about her abusive childhood and what she went though. She reveals to him that she used to wish somebody would come in and stop her father, like Jay did with the abusive husband. She tells Jay that her mom is still living with her dad even after the years of abuse, which shocks him.

In Lines, Vanessa deletes footage to protect an ex-boyfriend, and Hailey covers it up for her. Hailey steps deeper into the dark side as she crosses lines of no return in order to help Rojas and her friend. She ends up planting drugs in their suspects vehicle in order to get a deal for Rojas' friend. Figuring out what she has done, Voight disapproves of her action and sends her to the FBI temporarily where she'll learn to see the lines again.

In Silence of the Night, Hailey and Jay have a conversation while she is in New York, and she confesses to missing him.

Season 8

The first episode of season 8, Fighting Ghosts, shows Hailey back from her time in New York with the FBI.

In Tender Age, Hailey get a package from the Feds while working a case, and from curiosity Jay asks her what the Feds want from her. She tells him they offered her a job in New York and he quickly lets it go. Later after they solve the case, Jay and Hailey have drinks at a bar and she tells him more about the offer and tells Jay that he could tell her not to take it. Jay tells her its a "good job for a good cop" and that she should do what she wants to do. Hailey tells him that she turned down the offer as she doesn't want to leave Intelligence and Jay, as she is better with Jay as her partner. Before they part way, she finally confesses her feelings saying "its been a long time since I saw you as just my partner". And Jay responds by kissing her.

In the following episode, Unforgiven, Jay and Hailey are shown in the bed together early in the morning, making out. They are interrupted by Hailey getting a text from her mother, saying that her dad had a heart attack and was at the hospital. Jay and Hailey head to the hospital to see him but on their way, they get a call from patrol about a body. Hailey says he will see her dad later and the pair heads to the scene. Throughout the episode Jay tries to be supportive of her while she’s battling with deciding if she’s going to visit her father in the hospital or not, considering his abuse on her and her family in the past. Hailey struggles with her father being hospitalized and Jay tells her that she should go see him for herself and not for her dad. While interrogating a suspect, Jay's comment to the suspect about people making mistakes and how good people forgive them, triggers Hailey and she takes it personally like Jay was referencing the situation between Hailey and her dad. Outside the interrogation room, Hailey confronts Jay about his comment and he assures her that he was on her side and just wants to help. She reminds him that she doesn't know the whole situation and doesn't want his help. The two continue to work on the case and are able to find the real suspect. Ultimately, she tells Jay that she’s gonna visit her father, and asks if she will see him later. Jay nods and smiles. Hailey heads to the hospital, but upon seeing her father, she can’t face him and walks away with tears in her eyes. Considering she was abused by him in her childhood, she can’t forgive him enough to go talk to him. Jay later goes to Hailey's apartment and asks how the meeting went. She lies about seeing her dad and tells Jay that it went well. Jay knows she is lying but he doesn't push for answers and the topic isn't brought up again.

In Signs of Violence, Hailey and Jay wake up at her place and plan their rare day off together. While still in bed, Jay tells Hailey that he loves her for the first time and Hailey reacts negatively. She quickly excuses herself and Jay tries to talk to her but she tells him that she needs to get her car to the shop and rushes out of her apartment leaving Jay annoyed. While driving, Hailey hears a radio call for a missing family during a wellness check and answers it. At the house, she finds blood and calls in the team. The team begin investigating the case and realize that there are a lot of holes in the missing family's life leading Hailey to believe that there is abuse involved. She sees alot of her childhood in this missing girl's life and delves deep into the case getting more involved with finding the missing kid, which worries Jay. When the team are at a dead end, Hailey tries to use ICE to threaten their suspect in telling them the location of the kid. Voight tells her no but she is adamant on finding the kid even if it meant crossing a few lines. She decides to go ahead and involve ICE without Voight's consent but Jay stops her, asking her to tell him whats going on. Hailey assures him that she is fine and just wants to find the kid, but Jay knows her and asks her to stop shutting him out. He worries that this case is bringing up bad memories from her abusive childhood, but she denies it and tells Jay that what he really wants to know is why she is willing to cross lines and risk her career. She tells him that he is trying to find a reason to leave her after seeing how screwed up she is. This leaves Jay speechless and the two partners go their separate ways. As she is about to give up, she finds a lead and is locates the girl in time. Later she and Voight talk, and she confesses that she almost crossed a few lines but admits that Jay convinced her not to. Voight praises her skills as a detective and tells her that she is great at this job because of how focused and unempathetic she can be toward suspects. But once a case like this gets to close to her, she lets her emotional side take over and is willing to risk everything to get what she wants. After questioning whether she is fit to be a cop, Voight tells her that she can use this weakness to become and even better cop. Hailey later goes home and is surprised to see Jay waiting outside her apartment. Inside, she tells him how growing up, she was never allowed to show her emotions. Growing up in an abusive home, the words "I love you" always come after "I'm sorry". So when, Jay told her those words, it triggered her and she immediately thought Jay was gonna leave her. Hailey tells Jay that she wants to be with him, and Jay replies "I want to be with you too", assuring her that he isn't going anywhere. Hailey later tells him "I love you, so much" and the pair share a hug.

The partners continue to keep their relationship a secret from everyone, but their luck runs out in Safe. At the beginning of the episode, Jay and Hailey are seen going out on a date and sharing a kiss in his truck. The next day, they come into work hungover and after a small encounter, Voight suspects their relationship. He lets it go and the team start to work a home invasion robbery case. During a stakeout, Hailey is worried about the safety of their witness and makes a call against Voight's orders and Jay follows her lead. She realizes she made the wrong call which tips off their suspect. Voight isn't happy with Hailey's judgment and confronts her asking if she and Jay are romantically involved. He tells her that its a problem if her relationship is affecting how she polices. Hailey doesn't confirm or deny her relationship status and instead tells Voight she made the right call, and walks away. Back at her apartment, she tells Jay that she is worried that her actions during the case could have been influenced by her relationship and sets boundaries at work for them, which he agrees to. Hailey buries herself deep in the case, which concerns Jay. Eventually, she is able to locate their suspect and go to his house. At the house, Hailey wants to enter and see if the stolen jewelry are in there, but Jay tells her she can't as they have no warrant. Jay warns Hailey that getting to close to Voight can end bad for her and she assures that she just wants to solve the case, and heads inside. Jay has no choice but to follow her. Inside, they find the jewelry but their suspect comes home and they get made. They chase the suspect to a gas pump, where the suspect finds a hostage. To save the hostage, Jay shoots and kills their suspect. Later Voight asks what happened and when Hailey hesitates to answer, Jay lies and tells him what happened leaving out the part of them going inside the house. After their talk with Voight, Jay tells her that she had jammed him up and that he wasn't ok with it. Later, Hailey goes back to the district and finally tells Voight that she and Jay are dating, and asks for a new partner as she is worried her relationship is affecting her work. Voight denies her request and tells her that she and Jay are good partners and he isn't splitting them up. Before she leaves, Voight tells her to be careful and that they need Jay just the way he is.

In The Other Side, Kim goes missing during a raid and Intelligence does everything to find her. While Adam and Voight are willing to cross some line to find her, Jay and Kevin aren't, which leaves the team divided. Eventually Voight splits the team up, having Jay and Kevin work with Trudy to track the car Kim was taken in, and Hailey and Adam follow Voight and check out known associates of Roy Walton, the man who kidnapped Kim. Voight splits the addresses and has Adam and Hailey do one half, while he does the other. Hailey eventually realizes that Voight is having them chase dead ends, so after convincing Adam to go be with Makayla, she follows Voight and finds him at a warehouse beating Roy brutally. Knowing what he is going to do, she pleads with Voight to spare Roy's life and to bring him in as it's the right thing to do. Jay and Kevin radio in that they have found Kim and is bringing her to the hospital, and Hailey uses that to convince Voight to stop. Voight is hesitant as Roy is badly beaten and wants to get rid of the evidence, but Hailey begs him to not drag her down with him and he finally agrees. When Voight goes to uncuff Roy, Roy grabs Voight's gun and to save Voight's life, Hailey shoots and kills Roy. She immediately tries to stop the bleeding but Voight stops her and tells her to go home. Back at home, Jay is there already. He asks if she and Voight found any leads, which she says no. Not wanting to lose him, she tells Jay that she doesn't want to be without him, and asks him to marry her.

Season 9

Closure picks up right where the previous episode ended, with Hailey's proposal to Jay. Jay is shocked to hear this and wants to know why the sudden proposal. They are interrupted by a phone call and head to the hospital. As Kim's condition is still unknown, the team continue their search for Roy Walton and Hailey has a difficulty hiding the truth from the team. Eventually the search for Roy Walton is handed over to the Feds and Kim finally wakes up. Relieved to hear the good news, Hailey heads back home and find Jay there. The pair share a drink and Jay asks Hailey why she proposed, in which she tells him that she loves him more that anything and wants to be with him. Pleased with her response, Jay says yes and properly proposes to Hailey, telling her that he has known for years that he wanted it to be him and her always. She says yes to marrying him and the two share a kiss.

In The One Next to Him, the team finds out that Jay and Hailey are moving in together and tease them about their big change. Voight tells Hailey how the Feds are starting to dig into the disappearance of Roy Walton, which worries her. He tells her to stay calm and not to do anything out of the blue. Later on in the episode, Hailey and Jay share a meal in their new home, surrounded by moving boxes.

In the Dark is when Jay finally finds out about the secret Voight and Hailey are keeping regarding the night Kim was found.

In Trust Me, Jay has a hard time trusting Voight and following his command which gets in the way of their case. Eventually Hailey is fed up by his actions, and confronts him. Telling him that he can't let his anger towards Voight and herself get in the way of their case. Jay is still shown to be mad at Voight and Hailey for the Roy situation.

In Fractured, the FBI investigation into Roy Walton's disappearance heatens, as Agent North, the lead investigator on the case knows, Hailey and Voight had something to do with the missing person. Meanwhile, Hailey pushes for answers on a case, that seems odd. At the end of the episode, once the case is wrapped up, Jay calls Hailey and tells her that they are going to be alright, and that he loves her. In A Way Out, the FBI investigation continues, and Jay is left to make a difficult decision, Hailey or Voight. With some help from Voight, he is finally able to figure out a way out of this Roy mess. Later, once everything is wrapper up, he heads home and asks Hailey to marry him right now and the two partners officially get married.

Relationships

Partners

Erin Lindsay

Erin and Hailey meet in season 4 episode 21, Fagin. They get partnered up after Hailey joins the Unit in in the next episode. This causes a little awkwardness between her, Erin, and Jay due to the fact that Jay and Erin had previously dated and had been partners for the past 4 years. She and Erin are sent to find a victim and a suspect and the two of them have an honest conversation on the drive over. Hailey states that she didn't intend to "throw sand in the gears," when she inquires about Erin's relationship with Halstead, which Erin tells her, "not to worry about it," implying that it wasn't her fault. Erin adds, "It was probably time for a change anyway." They show that they can work well together and get along at the same time while talking to a suspect. Later in the episode, Erin uses her gun against an offender to find the location of a missing tender age boy. Hailey pleads for her to stop, but Erin tells her to leave. When she doesn't, the commander walks in and sees the situation. He benches Erin and Hailey for the rest of the case. Erin and Hailey are seen together waiting on the rest of the unit to get back from finding the kid, only to have Halstead and Olinsky tell them that the kid didn't make it. They are notified that they have to go up against the review board the next day for Erin's actions against the offender while he was in the interrogation room. In the next episode/season finale, Fork in the Road, Erin and Hailey finally go to the review board. Erin tells the board what happened, without a lawyer (FOP representative) present. Hailey goes with her FOP and backs up Erin, solidifying her loyalty to the unit. Eventually, Erin is forced to take the job offer from the FBI to save her mother and leaves Chicago.

Jay Halstead

Jay and Hailey meet in season 4 episode 21, Fagin. Initially, Jay and Hailey were on uneasy terms with one another because of a case that brought her unit (Robbery-Homicide) against his. After joining Intelligence in the next episode, and she becomes Jay's partner at the start of season 5, their relationship starts off rocky. This is due to the fact that Jay was still dealing with the heartbreak of Erin leaving, but slowly their relationship begins to smooth out; both become good friends and good partners.

Throughout their time as partners, they rely on each other as confidants and for comfort during rough cases. Hailey is the first to suggest Jay get some help after an undercover operation gone awry triggers his underlying PTSD. He declines saying “it’s not his thing”, to which she responds she will have to find another partner if he didn't. This results in him scheduling a therapy session and finally opening up during them. She often asks for updates regarding his sessions and is happy to know that it benefits him. Returning the favor, Jay visits her after a similar operation turned personal for Hailey and he realizes how deeply it affected her, deciding to share a drink with her instead of going to Molly’s with the rest of the Unit.

Over time, she and Jay grew to trust each other more as partners and began to develop a close friendship outside of work. They develop and understanding of each other deep enough to often communicate through eye contact, and they seek out each others advice and know when to step in to help each other out if they think one of them is at acting out during a case. They respect each others opinions and have voiced out their admiration and devotion of each other as their partners, both revealing that they'd follow the other anywhere. Their complete trust in each other is expressed by Hailey, in Good Men, saying "I trusted you from the day I met you." She also reassures him, in Outrage, that she'd never think he had murdered their suspect. In Reckoning, when the unit faces disbanding, Jay promises that he's going wherever she goes next in the job. In the same episode, he also protects Hailey by covering her with a vest and his own body when their surveillance van gets shot at. Neither end up injured.

Throughout season 7, the pair get closer than ever and relying on each other. They continue to show excellence in the partnership and comforts the other when. case gets to close. When Jay gets to close to a suspect's family, Hailey warns him to step away, but his stubbornness gets him in trouble. He is kidnapped in Absolution and Hailey does everything she can to get her partner back and shows worry. When the team finds Jay later in the episode and brings him to the hospital in Mercy, Hailey realizes her true feelings to Jay and almost confesses them to him at the end of the episode. Hailey is also seen to only open up about her past to Jay, sharing information regarding her abusive childhood to Jay in Intimate Violence. When Hailey is in New York for her temporary training with the FBI, Hailey confesses to Jay that she misses him. to which Jay teases her.

When she gets back from her time with the Feds, Hailey and Jay are able to get back to their normal routine as partners and friends. During Tender Age, Hailey gets a job offer from the FBI in New York and Jay seems happy for her but still sad by the situation. Later in the episode, after sharing the details about the job, Hailey tells him that she is turning down the job offer as she doesn't want to leave him or the team. She later confesses to her feeling to Jay telling him "It's been a long time, since I saw you as just my partner", in which Jay kisses her. They continue being partners and have never let their personal relationship get in the way of their job.

Romance

Jay Halstead - Upstead

Jay and Hailey were partnered in the first episode of season 5 following his ex-girlfriend and former partner, Erin Lindsay's departure from Chicago. From the start they showed a functional professional partnership, although they would sometimes show rocky patches during the first half of the season due to Halstead still trying to get over Erin leaving. However, they gradually become good friends and confidants, having the other's back during cases. Even in the first episode of season 5, Hailey expresses to him, “if there’s anything you need, please let me know”, effectively building a solid base for their looming partnership and friendship. It is shown that he cares for her as well in Fallen, where he expresses a similar “Let me know if you need anything” after a previous colleague of her ends up dead.

Season 6 showed their relationship deepening, from Endings where they first butt heads because of Jay acting out after his father dies, ultimately resulting in Hailey breaking down in tears after thinking Jay was dead when she and Ruzek find him shot on the ground. He's there for her in True or False, where a suspect she interrogated kills himself, saying he wants to make sure she's okay. In Trigger, Jay opens up to Hailey about his military past, which is something we've rarely seen in previous seasons. She comforts him and they head off to share drinks. Hailey meanwhile shows guilt about keeping her relationship with Ruzek from Jay, and though Jay insists that he gets it, we see hints of jealousy from him. For example, in Outrage, after having drinks at a bar, he tells her to go meet Adam with a half hearted smile. In Good Men, Hailey reveals that she trusts him completely, enough to follow him blind, which seems to leave him speechless. In Reckoning, when she says Jay will forget about her just fine, he shakes his head, indicating she means more to him than just a partner.

The next step in their relationship is taken when Jay is shot in season 7 episodes 10, Mercy. Not knowing if he's going to survive, in Absolution, causes Hailey to realize the extent of her feelings for him -- as Rojas points out, "it's hard because you love him." This episode also reveals how well the two know each other, as Hailey speaks of Jay's fear of needles (and hospitals in general), and he begs her to get him out of the hospital when he wakes up, saying she knows how much he hates them. At the end of the episode, Hailey comes close to telling Jay how she feels, though they are interrupted by a phone call and she realizes he's not in the right state of mind.

After Hailey is sent to the FBI field office in New York as Voight's way of punishing her for crossing lines, Jay shows concerns that she won't return, but she reassures him that she will because she misses him. In the next episode, he admits to Trudy Platt that he misses her as well.

After Hailey returns to Chicago, she later receives a permanent job offer from the FBI in Tender Age. Jay is shown to be bothered by this, and at the end of the episode they have a heart to heart conversation at a bar, where Hailey tries to figure out if he wants her to stay or take it. He evades answering as a way of "practicing self preservation", indicating that he'd be hurt by her leaving if he reveals how he feels first. She tells him she doesn't want to take the job because of him and the team. However, she admits that she is afraid that if she "gains something," she'll be "giving something up", insinuating if she reveals how she feels. She might gain a relationship but lose him as a partner, as they both know the struggles of working together while dating. He tells her that doesn't always have to happen, indicating he wants to give them a try, and she finally admits to him that, "it's been a long time since I saw you as just my partner." To this declaration of her feelings, Jay responds by kissing her.

In the following episode, Unforgiven, Jay and Hailey are shown taking the relationship forward spending their first night at Hailey's apartment. Their relationship continues to grow as they balance being partners and their new relationship, occasionally teasing each other. In Signs of Violence Jay decides to take the next step and say I love you to Hailey, but she has a negative reaction and decides to bury herself in work. Jay tries to get her to open up, but she continues to shut him out. Eventually Hailey finally opens up, telling Jay how the words "I love you" reminds her of the past men that leave her once they realize how much baggage she has. Jay assures her that he wants to be with her and isn't "going anywhere" and Hailey finally tells Jay that she loves him so much.

Their relationship is later tested, in Safe, when Voight finds out about the two partners secret relationship and questions Hailey's judgement on a case, wondering whether Hailey sided with Jay because of their romantic relationship or because it was the right decision. After her confrontation with Voight, Hailey later talks to Jay about setting boundaries at work to help her balance work and their relationship. Jay supports her decision but as the case comes to an end, their job comes between their relationship. They seem to recover from their disagreement because in the season 8 finale, The Other Side, Hailey proposes to Jay after going through a traumatic event, scared of not having Jay in her life.

Season 9, starts off right where season 8 ended, with Hailey proposing to Jay. Jay is shocked to hear this sudden proposal, but before he can reply, they are interrupted by a phone call. As the team continues to search for the man who shot Kim Burgess, Hailey struggles with hiding the truth about the previous night. After the team finally wraps up the case, Hailey and Jay have a conversation regarding Hailey proposal. She tells him how she loves more than she ever thought possible and wants to know that no matter what happens in life, everything will be alright as long as she has Jay. Realizing her honesty, Jay tells her yes and properly proposes to Hailey reminding her that he has known for years that he wants it to be him and her, always." The two are officially engaged at the end of Closure. Hailey and Jay move into their new home, soon after the proposal and start a new chapter in their lives. Although they are in a good place as a couple, Hailey is still no honest with Jay about the events that happened the night she proposed and has to carry the guilt. In In the Dark, Jay starts to realize that Hailey is hiding something from him and after a bit of digging, he finds out the truth and isn't very happy. Their relationship goes through a rocky patch as Hailey tries to gain Jay's trust again.

In Fractures, after realizing that he might end up losing Hailey, he decides to mend their relationship and tells her I love you, assuring her that they are going to be okay. In the following episode, as the case against Voight and Hailey intensify, Jay has to make a decision regarding who to protect. After he figures out how to deal with the mess and settles it, he comes home to Hailey and asks her to marry him now. In A Way Out, the two partners get married and enjoy a steamy moment.

Adam Ruzek - Upzek

Like with Jay, she initially was on uneasy terms with Adam, but later becomes friends with him after joining Intelligence.

While rarely partnered with Ruzek, she is often the one to keep him in line, and is unwilling to blindly follow him in breaking protocol. They were both in a romantic relationship with one another which started as a one-night stand, from Bad Boys to Sacrifice, wherein they both agreed they were better off as friends, as they both had feelings for someone else.

Garrett Thompson

Before joining the Unit, Hailey was once partnered with Garrett on an undercover op together. They were posing as a couple, to try and take down criminal boss, Ronald Booth. Hailey reveals to Jay that Garrett was killed during that operation. During that undercover, Hailey says that Garrett had been "talking ring sizes," indicating that either their UCs, or the two of them, were engaged, or about to be before he disappeared. Also, in Ghosts, Hailey reveals to Jay that she was in love with Garrett and that he had been the one to save her from Booth before he raped and killed her several years ago.

Friends

Trudy Platt

Trudy Platt served as her inspiration to be a cop as a kid.

When they met again, Hailey recognized her last name and mentioned their first meeting to Trudy, who had to recall this until being surprised at how Hailey turned out. Trudy was left with tears of joy after hearing that she had such a great impact on Hailey. Ever since, they remained on good terms.

Vanessa Rojas

Vanessa and Hailey got along really well. After Vanessa transferred to Intelligence, Hailey offered to bunk with her after hearing she doesn't have a place to stay, to which Vanessa was grateful for. Hailey grows really protective of her new room mate and temporary partner.

Kim Burgess

Though Hailey and Kim aren't shown to have that deep of a relationship, but they are friends and have been through a lot together. They were kidnapped, during which they helped each other through it. They've also shared drinks and hung out multiple times. Hailey was shown to have great sympathy for Kim after the latter had a miscarriage. She was also worried and respectful of Kim's feelings around Hailey's relationship with Kim's ex, Ruzek.

Kevin Atwater

Their relationship hasn't been dug into that much either, though they'll exchange occasional fist bumps, indicating a healthy friendship.

Notes and Trivia

  • Hailey is left-handed.
  • She uses a Glock 19 as her sidearm.
  • Hailey has so far driven a Jeep Grand Cherokee SRT and a Ford Taurus Police Interceptor; since Season 7, she started using a low-profile black Jeep Grand Cherokee SRT8.
  • She is Greek-American.
  • Her actress, Tracy Spiridakos, says she listens to metal and is a dirt bike rider.
  • Her radio code is 5021 Henry.
  • Her badge number is 55055.
  • Her father wanted her to be a lawyer.
  • She has a handle of speaking Spanish.
  • Like Jay, she has issues with her father.
  • Her Class A uniform displays the Superintendent's Award of Valor, Police Medal Award, Special Commendation Award, Arnold Mireles Special Partnership Award, and Police Blue Shield Award.
  • The team celebrates her 10 year anniversary as a cop in 9x13

Memorable quotes

To Voight: “I always heard you were a son of a bitch, now I know it’s true.” - 4x21

To Adam: "You can't hit people just because they piss you off! Not in front of me anyway." - 5x04

To Jay: "I'm done being your punching bag." - 6x02

To Jay: "We've only been partners for a couple of years, you'll forget about me just fine." - 6x22

To Voight: ”It takes a lot of time and trust to build a partnership that works and Jay and I are working.” - 7x03

To Voight: "I'm not saying he was a good guy, a right guy, a smart guy. But he was my guy. I put him out there! He was mine." - 7x07

To Jay: ”It’s a thing that works between us. One of us doesn’t want the other one around, the other one stays anyway. We talk, we feel better and we’re able to go to work the next day. It works." - 6x07

To Jay: ”I trusted you. I’ve trusted you from the day I met you, and if I was gonna follow someone blind, I’d follow you” - 6x15

To Vanessa about Jay: "Of course I love him, he's my partner." - 7x10

To Jay: "I'm better with you as a partner." - 8x03

To Jay: "It's been a long time since I saw you as just my partner." - 8x03

To Jay: "Jay, I do. I love you so much." - 8x11

To Voight: "After everything that you have spat at me, that I can't handle it, that I'm not gonna be able to sleep at night, that I'm not you, you're right, Sarge. I'm not you. But I am here now, and there's no going back. So you go cross whatever line you're gonna cross, but you remember that you are dragging me to the other side with you." - 8x16

Appearances

Season 4
The Silos Made a Wrong Turn All Cylinders Firing Big Friends, Big Enemies A War Zone
Some Friend 300,000 Likes A Shot Heard Around the World Don't Bury This Case Don't Read the News
You Wish Sanctuary I Remember Her Now Seven Indictments Favor, Affection, Malice or Ill-Will
Emotional Proximity Remember the Devil Little Bit of Light Last Minute Resistance Grasping for Salvation
Fagin Army of One Fork in the Road
Season 5
Reform The Thing About Heroes Promise Snitch Home
Fallen Care Under Fire Politics Monster Rabbit Hole
Confidential Captive Chasing Monsters Anthem Sisterhood
Profiles Breaking Point Ghosts Payback Saved
Allegiance Homecoming
Season 6
New Normal Bad Boys Endings Ride Along Fathers and Sons
True or False Trigger Black and Blue Descent Brotherhood
Trust Outrage Night in Chicago Ties That Bind Good Men
The Forgotten Pain Killer This City What Could Have Been Sacrifice
Confession Reckoning
Season 7
Doubt Assets Familia Infection, Part 3 Brother's Keeper
False Positive Informant No Regrets Absolution Mercy
43rd and Normal The Devil You Know I Was Here Center Mass Burden of Truth
Intimate Violence Before the Fall Lines Buried Secrets Silence of the Night
Season 8
Fighting Ghosts White Knuckle Tender Age Unforgiven In Your Care
Equal Justice Instinct Protect and Serve Impossible Dream The Radical Truth
Signs of Violence Due Process Trouble Dolls Safe The Right Thing
The Other Side
Season 9
Closure Rage The One Next to Me In the Dark Burnside
End of Watch Trust Me Fractures A Way Out Home Safe
Lies To Protect Still Water Blood Relation Gone
Closer Adrift New Guard Fool's Gold TBA

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