The first prophet that was introduced in Supernatural was Chuck in season four. Sam and Dean find out he wrote a series of books that chronicles the events of their lives. Archangel Zachariah shows up and tells them that, one day, Chuck’s books will be “the gospel of Winchester.” Chuck relieves visions that give him debilitating headaches, and then he uses the visions to write stories. He isn’t the only prophet, though.
In season seven, Kevin Tran is introduced, and his power as a prophet stems from being able to read the word of God from a tablet written by Metatron. Later, Crowley kidnaps future prophets, and, in season 11, Donatello is introduced. Chuck turns out to be a vengeful God. From the moment Sam and Dean meet him, the prophets are worse and worse.
Drunken Chuck, The First Prophet
Chuck isn’t the first prophet ever, but he’s the first prophet that Sam and Dean encounter. He’s drunk, he’s pathetic, and he’s drowning in self-pity. Chuck is plagued by visions that give him chronic headaches, and the only way he feels he can keep them away is by drinking copiously.
His books inspire a fandom that catches up to Sam and Dean often and they hate it. Chuck doesn’t care about that, though. He keeps going and acts like he’s the victim.
Kevin Tran, Advanced Placement
Kevin isn’t a drunk like Chuck, and he’s found by the Winchesters in season seven, right after he became a prophet. He steals his mom’s car and is compelled to drive far away to get to a tablet with the Word of God written on it by Metatron. He is afraid and completely clueless, which is even worse than drunken Chuck. Kevin’s ignorance of the situation makes him a liability and a flight risk, which is more work for Sam and Dean than dealing with Chuck’s growing fandom.
They Brought The Wrath Of The Archangels
When the archangels are trying to get Sam and Dean to play their roles in the apocalypse, they appear at the home of Chuck and let them know that every prophet has an archangel watching over them. The brothers used this fact to bring the wrath of the archangels when he was in the same room as Lilith, but, when it came to Kevin Tran and later prophets, the angels on their trail became an increasingly worse and often life-threatening issue.
The Metatron Problem
The prophets are able to read The Word of God from tablets written by Metatron. When this is discovered not just by Sam and Dean but also by Crowley, that information becalmed more valuable than ever. Other people searching for the tablets brings Metatron out of the woodwork, and his involvement ultimately leads to the angels falling from heaven.
This event sets many more into motion, culminating in Metatron attempting to be the new God. When the angels fall, Sam had been attempting the trials and almost died. Metatron's actions gave the angel Gadriel the opportunity to possess Sam when Dean has a desperate need for help. This puts Gadriel in the position to murder Kevin. After this, Metatron claims he fixed it so that no other prophets would be activated.
Chuck Comes Out As God
As if Kevin’s death wasn’t bad enough, the prophet Chuck returns in season 11 and reveals himself to be God. But, he’s not there to fix all the things The Darkness destroyed. He was manipulating events all along as the writer and crafter of the whole story.
“The Gospel of Winchester” was his design, as was everything else. Chuck as God was disappointing to the Winchesters, to say the least. It was so much worse than Chuck being a drunken prophet. At least, as that character, fans had pity for him.
Donatello, The Soulless
The next prophet that Sam and Dean encounter is Donatello, and his soul is taken by Amara, The Darkness. His condition causes a new set of problems, not least of which is that he’s out for himself. Donatello doesn’t want to help anyone, and he has no moral com compelling him otherwise since he has no soul.
At a time when the Winchesters need a prophet the most, to track Amara, they’re stuck with Donatello because the prophet Chuck is really God and he made his big sister, Amara, angry. The situation is particularly desperate since the Winchesters have no idea if they’ll encounter another prophet if Donatello dies, as per Metatron’s claim after Kevin’s death.
The Many Forms Of Kevin
After Kevin’s death, he appears as a ghost stuck in the veil that asks Sam and Dean for help finding his mother. Later on, after Chuck says “welcome to the end” and the gang is in major trouble, Kevin appears again, this time to help them.
He tells the Winchesters that Chuck threw him into hell, but the reasoning isn’t exactly logical or clear. There’s also Apocalypse World Kevin who is a drug addict who helps Michael kill and torture people from the human camps. The many iterations of this prophet are confusing for fans and convoluted for the plot.
Donatello Goes Dark Side
Donatello goes untapped for a long time until he senses Jack’s birth. He helps Sam and Dean in many ways, including recognizing that Jack’s energy isn’t evil. When Sam and Dean need to open a rift into the Apocalypse World so they could save their mother, they called on Donatello again to translate the demon tablet and find a spell for them. He did, but not before the demon tablet corrupted him.
With prophets of the past, the soul tempered this issue and stopped them from being corrupted. But, Donatello doesn’t have a soul, and the corruption causes him to turn dark and then betray Sam and Dean. They still need the spell, though, so Castiel takes it from Donatello’s mind forcibly, and that leaves Donatello braindead.
The Tragic Case Of Tony Alvarez
A new prophet is supposed to be activated when one prophet dies. Donatello was braindead, and that sent a sort of misfire to activate the next prophet, Tony Alvarez. His powers don’t come in the same way as any other prophet. Instead, Donatello’s healing mind was resonating in Tony’s as the word of God telling him to enact divine retribution on sinners.
He kills two people and attempts to kill a third before he is caught and then he kills himself. After this utter tragedy, the Winchesters and Castiel come to the conclusion that the succession of prophets will always be corrupted this way until Donatello is completely dead.
Donatello’s Failed Redemption
Before Sam, Dean, and Castiel make the decision to kill Donatello, Castiel figures out that his brain is healing and he is able to wake Donatello up. He still has no soul, but he appears not to be corrupted by the demon tablet anymore. He has no memory of his betrayal and goes about his life exactly as he was.
Nick, Lucifer’s vessel, tricks him and captures him. He finds out that prophets can be used as conduits to The Empty and wants to use Donatello to reach Lucifer. Nick’s plan is successful, and, through Donatello, Lucifer tells Nick how he can come back. The ritual revealed by this encounter leads to Nick coming for Jack’s blood, literally.