Lucy and Winter

The realtionship between Lucy St James and Winter Greene. Their relationship for the first seasons is strictly professional, with the pair hardly ever interacting other than when Winter hands out assignments to the squad. After Lucy and Messer enter into a relationship, things become more tense between Lucy and Winter. When Messer leaves Helios to start his own investigations division, Winter becomes closer to Lucy in an attempt to manipulate her into exposing Messer and targeting them against each other. Things come to a head when the Helios headquarters are set on fire, leading to the death of Luke, which Winter blames Lucy for.

Season 4

Despite their previous tense relationship, Winter starts to soften up to Lucy as she becomes fearful of Messer's potential revenge against her and Helios. At the start of the season, Winter calls Lucy into her office where she tries to pick apart Lucy's relationship with Messer, despite the wounds of their very recent break up. During their meeting, Winter tries to convince Lucy that Messer was only using her to fulfil his loneliness after his divorce with Rachel and also to gain more people onto his side, as she believes branching off from Helios was his intentions all along. She manipulates Lucy into believing that Messer never truly cared for her as she was "out of his league", and that he knew that she would be easy for him control as she has always been in love with him. When Lucy tries to deny this, Winter tells her that if Messer truly loved her, then he would have told her of his plans and he never would have left Helios without her.

Although Lucy tries to reject Winter's words, during the sleepless and lonely nights they begin to eat away at her. She often calls Messer's phone number although it has been disconnected just to hear his voice on his answering machine. While walking Hedgecliff one night, she passes by their old apartment and becomes saddened when she sees that a new couple with a young toddler have recently moved in, and all the memories they made there are gone. Lucy begins to feel depressed without Messer, and although she tries to start dating again, she finds that no one interests her like he did.

When Lucy and Messer meet again at the Tranquility Hotel, Messer warns Lucy to becareful of Winter. He confesses about the sexual assaults that she made against him and how she tried to manipulate him throughout his years at Helios in a predatory/grooming sort of way. Lucy doesn't completely understand this as she believes that Winter is with Luke, but takes Messer at his word.

After Lucy completes the Tranquility Hotel mission, and upon learning that Messer was a crucial part to gathering the evidence, Winter becomes furious toward Lucy and questions her loyalty to Helios. For the first time, Lucy begins to argue back against Winter, now starting to believe Messer's warnings about her. After the meeting, Winter assigns Lucy to a "trust test" despite her knowledge. When Lucy returns to her apartment, she finds that it has been torn apart and many of her things have been stolen - including her spy equipment and killing her dog Hedgecliffe. While the cameras have been cut, Oliver is able to recover the footage and finds a small clip of a man who looks like Messer entering her apartment with another masked woman. This leads Lucy to believe that Messer was using her at the Tranquility Hotel, and that his new partner was the one who killed Hedgecliffe when he attacked her in defence.

Lucy flies into a blind rage and begins passionately helping Winter to hunt down Messer. During their mission, Winter and Lucy become closer as friends, and Lucy begins to think that she misunderstood Winter this entire time due to the things often said about her. Winter opens up to Lucy about her past, and they are able to connect on an emotional level when Winter reveals that she was adopted by a former Helios agent who trained her brutally during her childhood, all with the intention of having her one day become Director, though he died before he could see it happen.

At the climax of the season, Messer (with the help of Lucy) is captured and taken to be tortured and interrogated. After having a heart-to-heart with Winter, she allows Lucy to sit in on one the interrogations and ask Messer questions through a one-way mirror and into the earpiece of the agent in the room. During the interrogation, Messer catches on that Lucy is the one speaking through the agent. He calls out to her, imploring her to believe in his innocence and to help him. Winter whispers into Lucy's ear in an attempt to keep her on their side, and this sends Lucy into a rage, causing her to lunge to the speaker and accuse Messer of killing Hedgecliffe. Messer reacts in shock and pain when discovering Hedgecliffe's death, which causes Lucy to suddenly realise that he wasn't the one who committed the deed, and that she has been lied to and manipulated this entire time.

Lucy quickly swallows this realisation and leaves the interrogation room with Winter. Winter appears notably suspicious of Lucy, and they go to "cool down" in her meeting room, where a tense conversation plays out. When Lucy realises that Winter knows of her switched loyalty to Messer, Lucy lunges for her pistol at the same time Winter does. A fight breaks out between the two, with both women kicking around and trying desperately to get their hands on the gun. Winter manages to get the upperhand and stabs Lucy in the shoulder with a knife kept under her desk, she then climbs on top of Lucy and presses the knife to her throat, but stops before she can kill her as Mayor Jefferson has entered the room. Lucy calls for help but Jefferson smiles down at her before helping Winter rise to her feet. They reveal that they have made a pact together, despite their former public feud, in order to make Helios theirs and have power over the entire country. Lucy tries to tell them that their wont get away with it, but doesn't get to finish her sentence before she is swiftly kicked in the head by Jefferson.

Some hours later, Lucy awakens to the sound of an alarm going off and the smell of smoke. In writhing pain from her shoulder and concussed from the kick to her head, Lucy crawls out of the room just as a loud explosion goes off. She slowly stands, and sees through the glass that the West Wing of the Helios Headquarters has exploded. There are loud screams, and a few of the workers go running past Lucy, dashing to the elevators. Lucy tries to grab them to ask what is happening, but no one stops to listen to her, not even when she tries to pull rank. As another explosion goes off - somewhere unseen - Lucy remembers that Messer is downstairs in the interrogation rooms. She quickly runs to the stairs, trying to push past the escaping employees as they flee in the other direction.

Bleeding and in pain, Lucy makes her way down the long flight of stairs to the basement. As she goes, another explosion rocks her and she loses her grip on the railing and tumbles down the stairs, slamming her head against the brick wall. She blacks out for a moment and tries to crawl forward, desperate to get toward Messer. (During this time, we also see Max and Monty's reactions to the attack, and Winter arriving to reveal that Messer's rebellion has caused it). She eventually makes it down to the interrogation room, and stumbles into Messer's room, where he is still tied to the interrogation chair though he has been beaten bloody - not at all as he appeared when she last saw him. Messer sees Lucy through his bruised and swollen eyes and calls out a warning. Lucy turns around, just in time to catch Jefferson's arm as he tries to stab her with a knife.

A fight ensues between Jefferson and Lucy. Despite her training, Lucy is at a disadvantage due to her injured arm and head. Jefferson gets the upper hand and falls onto the ground on top of Lucy, attempting to strangle her. As her vision goes blurry, she manages to reach up and unlock the cuffs holding Messer's legs, and he wraps them around Jefferson's neck and breaks it. Lucy gets up and frees Messer, and they hug each other lovingly, relieved to know the other is okay. They leave the interrogation room together, hand-in-hand, but cannot escape back up as the flames are too thick there. They go the other way, deeper underground and enter the garage which is empty, as everyone working there has fled due to the bombs. Messer enters the code for the garage gates while Lucy breaks into the control room to take keys for one of the cars. Just as she grabs it, a gunshot rings out and she sees Messer fall as he is shot in the back.

Lucy screams and runs out toward Messer, but stops when a familiar voice calls out "Stop!" She turns, hands raised, to see Luke standing there in front of them. He has been convinced by Winter - his lover - that Messer's gang truly has caused this attack in order to free him. Lucy pleads with Luke, trying to convince him that Winter is evil and that he should either escape with them, or leave them be. Luke doesn't buy it, despite his strong friendship with Lucy, believing instead that she will always do whatever she can to protect Messer. As Luke steps forward, he is suddenly shot in the head by Messer.

Lucy is horrified at the death of their beloved friend, but there is no time to react. Messer is dying from his gunshot wound. Sobbing and injured herself, Lucy grabs Messer by the arms and drags him toward the car she chose, pushing him into the backseat. She gets into the drivers seat and drives out of the garage, crying and begging Messer to hold on. We see him watching her through blurry eyes, and begins to murmur, "I love you..." before everything goes black.