Sam and Dean Winchester were brothers destined to become the vessels of Lucifer and Michael respectively, so the latter could complete their rivalry and argument on Earth during an event known as "The Apocalypse". Gabriel was Lucifer and Michael's younger brother, who had fled Heaven the last time the two brothers fought as he could not bear to witness such horrors.
Although Gabriel was aware of Sam and Dean's destiny, he was unwilling to partake in the event and instead he appeared to them under his guise of a deity known as The Trickster.
Posing as a janitor at Crawford Hall university, Gabriel began punishing various people on campus who were known for misbehavior, by serving them their "just desserts". The first victim, Professor Arthur Cox, was tricked into letting a girl into his office (something he often did) and fell out of his window after she revealed her mutilated face.
Sam and Dean came to investigate by posing as electricians. Gabriel let them into the professor's room and told Sam (while Dean munched on nuts) about the professor's tendency to pick up girls, and on the night of his death, Gabriel had seen a girl go in but never come back out. Gabriel joked around with the brothers, who seemed delighted by his presence, before they left.
As more and more victims experienced weird occurrences that didn't always end up in death, Sam and Dean requested Bobby Singer to come over and help them out. Prior to that, Gabriel had begun pulling pranks on Sam and Dean too, causing the brothers to fight each other. Bobby deduced that they were dealing with a Trickster, leading Sam and Dean to suspect Gabriel.
Sam investigated Gabriel's locker room and found magazines about aliens, which had apparently abducted a school boy earlier. This confirmed Sam and Dean's suspicion. In an attempt to trick Gabriel into thinking that the two of them were not on good terms, Sam and Dean argued outside the university while Gabriel watched. Dean then entered the theater to find two of Gabriel's illusions, posed as scarcely dressed women, offering themselves to him on the stage.
Gabriel told him that the women were a peace offering, in exchange for Dean allowing Gabriel to skip town since he did not want to hurt them. Although Dean was visibly tempted, he declined letting Gabriel leave, and revealed the truth; he and Sam did not argue, but Sam and Bobby had gone to retrieve a stake dipped in the blood of one of Gabriel's victims in order to kill him. Gabriel was impressed, but since Dean refused to make a deal, Gabriel crafted more illusions and had them attack the trio as he watched gleefully.
Unfortunately, Dean managed to stab him in the heart with a stake, and Gabriel died while his illusions dispersed. After the brothers had left, Gabriel was revealed to have survived the encounter simply because a fake one had been in the theater the whole time.
As Dean's crossroads deal neared its deadline, Gabriel came to the understanding that Sam needed to learn how to let go of Dean. He believed the younger Winchester was obsessed with his brother, which was a vulnerability others could use to their advantage. Although his motives can be considered good and his reasoning sound, Gabriel's methods were anything but.
After Gabriel dumped Professor Dexter Hasselback into a wormhole to prove to the man that wormholes existed, Sam and Dean arrived at the professor's last known location to investigate his disappearance. From the moment they woke up, the brothers had been trapped in a time loop which would repeat itself continuously. Each day, Dean would suffer random deaths despite Sam's attempts to keep him safe. The lesson was to teach Sam that he was going to lose Dean anyway, so he should just let go.
Sam was distraught, becoming increasingly frustrated with the repeated Tuesdays, but he also grew well accustomed to his surroundings, and recognized when one of the customers in the diner had a different flavored syrup on his pancakes. Sam confronted the man, who revealed himself to be the Trickster they thought they had killed nearly a year before.
Gabriel admitted that he enjoyed killing Dean, but he also wanted Sam to lose his obsession with Dean. Threatened with a stake, Gabriel appeared to give in to Sam's demands and freed them from the time loop. However, by the next day, Dean was shot dead and the day did not repeat itself. Sam lived in what appeared to be the real world and spent months trying to get his hands on Gabriel. The lesson grew tiring for the archangel, who lured Sam to his location so he could try and convince Sam point blank the meaning behind his lesson.
Sam did not listen, acting like "a brick wall" in Gabriel's own words. Gabriel gave up, and finally freed Sam from his continuous nightmare, either by reviving Dean or by freeing Sam from a time loop. Dean woke up with no recollection of the events.
It had been approximately two years since Gabriel had last confronted the Winchesters, but things had become personal since the pre-destined Apocalypse was now above them and Gabriel was to witness once again a fight between his brothers.
|“||You're going to suck it up, and play the roles that destiny has chosen for you!||”|
— Gabriel to Sam and Dean.
in Changing Channels
Longing for the fight to end swiftly so he would not have to endure it, Gabriel pulled his usual pranks on various people to lure Sam and Dean to his desired location, before sending them into TV land.
Dean's obsession with the Dr. Sexy series enabled him to figure out who Gabriel was posing as. Gabriel pretended he simply wanted to mess with Sam and Dean, ignoring Sam and Dean's attempts to get his help. He insisted that if the brothers wanted to talk, they should survive the next 24 hours. Sam and Dean were forced through more television-based universes, until Castiel broke in and tried to warn them of the person they were dealing with, hinting that it was not a Trickster.
Gabriel made an effort to lock Castiel away to keep his identity hidden, which angered Dean who insulted him. Being far stronger, Gabriel quickly pinned Dean to the wall and demanded the brothers to "play their roles" as they were already doing in TV land but as the vessels for his brothers. He blamed Sam for bringing about the Apocalypse by freeing Lucifer, and assured them that he was not working for either of the archangels. However, Gabriel intended to keep them locked up in TV land until they agreed to say "yes".
Unfortunately for him, the brothers learned from Gabriel's behavior and his encounter with Castiel that he was most certainly an angel. They pretended to surrender before they trapped him in holy fire, which Dean dared Gabriel to jump out. With no choice, he admitted the truth: he was Gabriel the archangel, and he was trying to hasten the inevitable battle. While they ask for help in stopping it, he insisted that nothing could stop the fight from happening, Dean argued that Gabriel was simply being a coward by not standing up to his family. Dean had him bring Castiel back and soon freed Gabriel from the trap, leaving the archangel soaked in water and forced to contemplate his next move.
Sam and Dean fell into a trap set up by a group of pagan deities, who wanted to use them as bait in order to overthrow the archangels now messing with the world. Gabriel felt obliged to rescue them, but his attempt to do so failed when the leader of the group and his former fling, Kali, knew who he was and made an attempt on his life to prove to her associates that archangels could be killed.
However, Dean discovered the real Gabriel hiding in his Impala. The three were currently trapped due to Kali holding them hostage through possession of blood vials. Gabriel's attempt to retrieve them failed, so he urged Dean to do it. Dean did not, instead he urged Gabriel to stop being afraid. Lucifer was on his way and Dean needed Gabriel to be brave enough to confront him. Dean could tell that Gabriel cared for the pagan deities, and while Gabriel did not verbally agree to go back inside, he acknowledged Dean's words. Dean also ratted out Gabriel's ruse to the pagans and stated he was no help.
When Lucifer had killed all but one pagan deity (who was Kali), Gabriel arrived and saved her. He helped Kali and the brothers leave the hotel as he stood, for the first time in eons, in front of his older brother. By then, Gabriel had passed on a DVD to Sam and Dean containing the secrets about the Four Rings of the Horsemen. It was this gift that, despite Gabriel's "death" at Lucifer's hands, enabled the brothers to open the Cage and throw Lucifer (as well as Michael) into it, thus ending the Apocalypse and stopping the fight.
Gabriel was, alongside Crowley, Sam and Dean's most valuable new ally at the time.
It is revealed, but unknown to the Winchesters, that Gabriel was never killed and was held hostage by Asmodeus.
After they are sent to the Scooby-Doo Universe, the Winchesters remember how Gabriel previously did something to them and briefly wonder if he's responsible. However, they remember that he's "dead" and dismiss the idea.
However, Dean unknowingly hinted at Gabriel being alive as he mentioned the possibility of his survival.
|“||Gabriel, man what happened to you?||”|
— Sam to Gabriel.
in The Thing
After they return to the bunker, the brothers noted they need archangel grace. Arthur Ketch arrived and revealed the still living Gabriel to them as a gift, to Sam and Dean's shock as they had believed Gabriel dead. Seeing his state, Dean asks what Arthur did to him as the latter explains that Asmodeus had been holding Gabriel prisoner until Arthur rescued him. Once Arthur brought up their need of an Archangel, Sam decides to use Gabriel's grace to perform a ritual, to save their mother and Gabriel's nephew Jack. Gabriel is fearful of this and freaks out until Arthur calms him down, this reaction concerns them. Arthur then hands the brothers a vial of Gabriel's grace that Asmodeus had previously extracted.
Later, Sam tends to him by cutting the stitches holding Gabriel's mouth shut and asks Gabriel what happened to him. Before Gabriel can respond, Dean interrupts with the intention to travel to Apocalypse World immediately. Dean entrusts Sam to look out for the still disheveled Gabriel before he and Arthur pass through the rift, leaving Sam and Gabriel alone in the bunker.
|“||The world needs you. We need you. Gabriel... I need you.||”|
— Sam to Gabriel
in Bring 'em Back Alive
Gabriel is tended to by Sam and shows no signs of improvement only showing fear. Sam tried to get through to him as he is told by Castiel that Gabriel might be too gone but Sam keeps trying to speak.
Very soon, Gabriel reveals his story of how he faked his death and went into hiding before he was captured and sold to Asmodeus. Seeing some hope, Sam tries to get more out of him even telling him he needs him to return to his right mind and starts to leave but Gabriel speaks to him. Relieved, Sam and Gabriel talk before he was given his grace but Asmodeus (who sensed Gabriel regaining power) attacks the bunker to reclaim his prize. As Gabriel is taken, he watches Sam and Castiel being tortured by the Prince of Hell but he breaks free of his captors and stops him.
Sam watched the confrontation between them, which ended with Gabriel easily destroying Asmodeus. Afterwards, Sam caught Gabriel up on everything that has transpired, such as An alternate universe Michael trying to invade their world and his nephew Jack being sent the other world. Sam asked Gabriel to help them but he declines and tells them that he will put his faith in them as he did before. Even after Sam begs him again, Gabriel declines as he wanted no part in the conflict and he left the bunker.
When Dean returns, he is informed of the events that occurred but was angry at Gabriel's refusal to help. Castiel swore to Dean that they'd find Gabriel again, which Dean agreed too.
The Winchesters are tracking Gabriel, to get him to join them but have no luck.
The brothers tracked Gabriel with help from Rowena. Stopping at a motel, they wonder if they'll find him but having sensed Rowena's spell, Gabriel instead comes to them heavily wounded. Sam tends to him as the brothers question him.
They are then attacked by Sleipnir and Narfi who demanded Gabriel. After a fight, Dean handcuffed Gabriel and pressed him for answers and he begrudgingly tells them of what happened after he faked his death. Gabriel then revealed the pagan Loki and his sons had him kidnapped and sold to Asmodeus. The brothers listened to Gabriel reveal his intentions to settle the score and saw he was insistent on finishing it.
Dean criticized Gabriel by stating that his predicament wouldn't have happened if he had help in the Apocalypse. Gabriel voiced he had better things to do than help them and justified by telling them he helped by telling them how to trap Lucifer. Gabriel then declared he was going to finish what he started by killing Loki.
They offered him help but only if he will help them in their endeavors and he begrudgingly agreed.
When Dean confronted Loki, he defended Gabriel after Loki told him his reasons for turning on his old friend. The Winchesters also helped Gabriel by giving him the sword needed to kill the Pagan.
After killing Loki and his forces, Gabriel thanked the brothers for their help before he decided to move on from his past as a Trickster and help the Winchesters with Michael. Though surprised by this, they ask Gabriel if he is sure and he confirms as he promised to help them.
Gabriel continued to help the brothers by trying to provide grace for the spell but it wasn't enough. After Sam came up with a plan, Gabriel played a part by revealing himself to his brother Lucifer who he and Rowena captured and brought to the Winchesters to power the rift.
Gabriel then traveled with them to Apocalypse World to rescue his nephew Jack and Mary Winchester. When Sam was taken by vampires, he appeared worried as he told Jack that he wasn't strong enough to resurrect Sam. Gabriel was shocked to see Sam alive but with Lucifer who brought him back.
When Lucifer appeared, Dean ordered Gabriel to kill him since he was the only one who could but Gabriel was unsure. Gabriel continued to aid the Winchesters in their endeavors and just like them wasn't keen on Lucifer being on their side.
As they were evacuating the humans from Apocalypse World through the Rift, Michael appeared. The three were shocked to see him in person before they watched him easily defeat Lucifer. After Michael notices him, Gabriel told Dean and Sam to retreat as they tried to talk him out of it but he wanted to make up for his past and engaged Michael. The brothers witness the fight between the archangels and were horrified and visibly saddened when Michael quickly killed Gabriel.
However, Gabriel's sacrifice wasn't in vain as it stalled Michael long enough and stopped Lucifer from trying to go to their world as they retreated.
- Gabriel is the first angel, archangel, and primordial entity Sam and Dean met. He was also the youngest out of both.
- Gabriel is the only archangel to date to become Sam and Dean's ally and stay that way.
- Lucifer had briefly become allies with Sam and Dean in We Happy Few.
- Gabriel is one of very few angels overall to ally himself with Sam and Dean, another is Joshua.
- Gabriel's behavior towards Sam in Season 3 may reflect his own past, being forced to abandon a beloved older brother despite his desire to keep him. This may be a reference to Lucifer, who became - in Gabriel's own words - "a big bag of dicks" following his first imprisonment in The Cage.
- Although they are allies, Dean tends to be on edge when working alongside Gabriel, going as far as ridiculing his plan of revenge in Unfinished Business. However, by Beat the Devil and Exodus, Dean appears to have let this go. In spite this, Sam appears to be more welcoming of the archangel, willing to ask for help from him in Changing Channels and tending to him in The Thing, Bring 'em Back Alive, and Unfinished Business.