There are certain characters in Supernatural that were never meant to have redemptive qualities. While the Winchesters have lost the moral high ground several times, Lucifer and Azazel were never placed in a sympathetic light, as their purpose was to antagonize the heroes.
Azazel was the yellow-eyed demon who killed Mary Winchester and began the Winchesters’ crusade against monsters, while Lucifer’s status as the devil made him Azazel’s leader and “father.” Both villains caused numerous problems for all the Winchesters. Due to this, there are good arguments to consider either character as the archenemy of the family.
10 Azazel: He's Been Involved With Each Member Of The Family
All things considered, Azazel is the one responsible for the characterizations of Sam, Dean, and John. He had personal antagonistic connections to each member, stemming from his deal with Mary, who was the first member of the family to be his enemy.
John saw Azazel as his direct rival, as he became a hunter with the sole purpose of confronting the demon. Sam and Dean saw Azazel as the character responsible for their tragic childhood, with the three male Winhcesters sharing their resentment for him. As far as Lucifer is concerned, only Sam and Dean could claim to be his true rivals from the Winchester clan.
9 Lucifer: His Antagonism Of Castiel To Hurt The Winchesters
Castiel wasn’t a Winchester but the brothers were always directly affected by anything that happened to him. Lucifer killed Castiel in both Seasons 5 and 12, with the latter instance shattering the brothers' spirits. In addition, Lucifer took possession of Castiel for the majority of Season 11 to spy on the Winchesters and used this possession to taunt them.
The brothers were manipulated thoroughly by Lucifer during this time, as they couldn’t harm him without hurting Castiel in the process. This made Lucifer the villain who sunk to petty levels in his fight against the Winchesters, who were rarely this helpless.
8 Azazel: He's Caused Tragedies To The Family Across Time
The Winchesters were truly never safe from Azazel, seeing as the demon never let them go throughout much of their lives. In fact, Azazel killed people from their families in the 1970s, ‘80s, and the 2000s. These were the killings of Mary’s parents, Mary herself, and the deal John made for his life.
Even after Dean killed him, Azazel ended up encountering him once more in the past. Essentially, the Winchesters were always under threat from the villain, who seemed to find causing them pain and trauma particularly enjoyable.
7 Lucifer: Every Conflict Leads To Lucifer's Involvement
Interestingly, Lucifer had a hand in just about every conflict the Winchesters had, even the ones where he wasn't directly involved. After all, Azazel began his quest against the family acting on Lucifer’s orders, whereas foes like the Knights of Hell were the products of the devil to begin with.
Lucifer was also the one who hid the Word of God tablet, which became the focus in the season where the devil wasn’t seen. His status as Jack’s father was what ultimately led to the final arc of the series as well, meaning that all of the Winchesters’ problems arose as a result of Lucifer.
6 Azazel: Taking Him Down Was The Winchesters' Main Mission
The first two seasons feel different compared to the rest mainly due to the goal the Winchesters had. At this point, their main motive was to end Azazel, which kickstarted the series’ story. In-universe, this mission had gone on much longer.
The Winchesters had actually been hunting Azazel as far back as 1983, with their success finally coming in 2007. That means their true quest was always to get to Azazel and everything that happened after that was never part of their plans.
5 Lucifer: His Personal Connections To Sam
Over the course of the series, both Sam and Dean filled the role of the villain at various points. Lucifer was responsible for many of Sam’s tragedies, having tortured him relentlessly from Season 5 to 7 and resumed this in later seasons as well.
Since Dean’s reason for living was Sam, this had the effect of ruining his life as well. Lucifer’s connection with Sam was at its worst in the seventh season, where his hallucination brought him to near insanity. Of course, there’s also the fact that Sam is supposed to be Lucifer’s true vessel, thus cementing the latter’s role as Sam and Dean’s overarching villain.
4 Azazel: His Role In Tearing The Winchester Family Apart
It’s not just that Azazel killed Mary, but the fact that her death effectively broke the family. After Azazel burned her in the family home, John became obsessed with capturing him, to the point where his sons never had another home and were always on the road.
Sam’s relationship with John grew to be a bitter one as the youngest Winchester didn’t share his father’s obsession while Dean was always stuck between the two. All this family conflict was Azazel’s doing, who had ensured the Winchesters would never know true peace.
3 Lucifer: He's The Longest-Running Antagonist For The Winchesters
Despite first appearing in person during Season 5, Lucifer’s role as the antagonist was actually set from the get-go since Azazel worked on his orders. Starting from Season 4, he truly became the grand-scope villain and continued in this role later on.
After his return from the cage in Season 11, Lucifer once again became the central antagonist and was gone for only a couple of years when he made his return in the penultimate episode. The Winchesters saw lots of foes come and go, but Lucifer was the constant, and most of their plans involved vanquishing him from their lives.
2 Azazel: He's The Brothers' Greatest Fear
The brothers were shown their greatest fear on a few occasions, and it was Yellow-Eyes who would show up. Dean saw the demon when he was inflicted with ghost sickness, who was shown possessing Sam. In the Season 6 premiere, Dean’s hallucination caused by the Djinn had Azazel attempt to kill him.
No matter how many monsters the brothers faced, it was Azazel who inspired the most fear in their hearts. The family saw him as the representation of all that was evil and this didn’t go away even decades after Azazel had been killed.
1 Lucifer: His Orchestration Of The Entire Lives Of The Winchesters
In the Season 5 finale, Lucifer revealed that not only was Azazel acting on his orders but that he had been orchestrating their lives the whole time. Lucifer had his demons placed wherever Sam and Dean were, with some of their friends having been demons the whole time.
Lucifer was responsible for the direction the brothers’ lives took, having planned on manipulating Sam to give consent to his possession and for Dean to do the same to Michael. In essence, the Winchesters didn’t realize that Lucifer had dictated their lives all that time. When they did find out about this, the brothers understood that Lucifer was their greatest enemy all along.
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