Hailey Upton

**Detective Hailey Upton** is a member of the Chicago Police Intelligence Unit.

## Biography

As a child, her father 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 12, 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 countless childhood abuse, inspired Upton to become a policewoman, where she originally became a member of that same Robbery-Homicide unit.

She is later joined Sergeant Hank Voight's Intelligence Unit.

### 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 but the chief speaks in favor of Intelligence. Hailey is allowed to work with this case and her own dealings with the case helps uncover teen robbers being given orders by a former convict who cannot himself perform robberies because of a physical impairment. She is also surprised that she is able take part in interrogation by Lindsay. At the end of the episode, Hailey complimented Hank for helping one of the youthful robbers so they can still live a life once out of jail. Hank soon 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 then chose to accept a job offer with the FBI in New York.

### Season 5

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.

In *Fallen*, Hailey is reunited with her old partner Sean McGrady, who is now a sergeant for a Narcotics unit. She shows disregard toward him due to a shaky workplace relationship. Because of her awkwardness, Jay implies that Hailey was once involved with him, but that is never confirmed. After approached by Voight, she is forced to work with McGrady on a case. When responding to a call from McGrady, she is shaken when he is found shot. After investigating his death, Upton finds evidence to prove that McGrady actually committed suicide. 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 bury the evidence to keep McGrady's name intact, in consideration for his children 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 and teams up with Halstead's partner Katie Morales to try and get through to him. This is continued into *Rabbit Hole*, where Hailey and Katie must work against him for his own good.

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 this weekend.

In *Ghosts*, Intelligence 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 and Katie get curious and reach out to Hailey's old case officer, Jeff Rafferty, to find out what really happened to his partner that day. Katie later confronts Hailey and asks what happened. Hailey tells her 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 beaten. Katie 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 and Katie find out and follow 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 get into an altercation. Hailey gets the upper hand and points a gun towards him demanding a confession for Garretts murder. Jay talks Hailey out of pulling the trigger asking her to trust him. Hailey lowers her weapon and Jay arrests Booth.

### 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.

At the end of *Endings*, continuing with *Bad Boys*, Hailey and Adam hook up, after an emotional day.

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 goes to 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 in 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.

*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.

In *Ties That Bind*, The team go undercover to bust guys selling gins. 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 *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.

### Season 7

*Familia* sees newcomer Vanessa Rojas joining the unit, and she is partnered with Hailey, who Voight appoints to suss Rojas out because he knew Hailey will be straight with him. Hailey 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 in her childhood. Ultimately, to catch their suspect, Hailey fires the shot to distract him, resulting in his death.

*Informant* shows Hailey's relationship with one of her CI's and how his death deeply rattles her. 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.

During *The Devil You Know*, Hailey is once again forced to work with the person who murdered her CI in *Informant*. A dark side is shown of Hailey, as she goes to extreme lengths to get justice.

## 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 find the location of a missing tender age boy. Hailey pleads for to stop her, 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 kid didn't make it. Erin is notified that she and Hailey 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.

#### 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.

### Romance

#### Javier Morales

*Main article: Jailey*

Javier and Hailey met through Javier's sister and Hailey's good friend, Katie Morales.

#### Adam Ruzek

*Main article: 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.

#### Katie Morales

Hailey and Katie are seen to have a close friendship. Hailey is the first person Katie confides in about her feelings for Jay. After Jay gets shot in Mercy and is put on desk duty, her and Katie become temporary partners by which time she becomes close to Katie's brother, Javi. As of season 8, her and Javier are dating and while Katie was apprehensive about their relationship, she still seems to support Hailey's relationship and judgment.

#### 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 50-21 Henry.
* Her badge number is 55055.
* Her father wanted her to be a lawyer.
* She has a handle of speaking Spanish.
	+ With this, she has especially impressed the Morales Family
* 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.
* After her first dinner with the Morales Family, Katie jokes that if she ever decides to try and break up with her brother with "as stupid of a reason as feeling like she doesn't fit in" that she'll have to deal with Katie.