|Dates||???? - 2015 (killed by Sam Winchester)|
|Episode(s)||10.18 Book of the Damned|
Well, there’s coincidence, and then there’s just providence. See, “The Book of the Damned,” it wants to be found. It wants to come home. Let me guess. You want to use it to get that gift off your arm, don’t you? Power is wasted on the weak. Now the book….can remove that Mark. But you mess around with that, you’re gonna do far more harm than good.
– Jacob Styne, 10.18 Book of the Damned
Jacob Styne's family are practitioners of black magic, stretching as far back as the early 1800s. Over the centuries the Stynes used spells to create disease, destabilize markets, and even help the Nazis rise to power; all the while profiting from the damage they caused. All the spells the Stynes used came from a book of "unspeakable evil" -- the Book of the Damned, which was lost to the family some 100 years ago. When Charlie Bradbury unearths the book in monastery in Spain, Jacob is sent to hunt down and retrieve the book for his family. He follows her all the way back to the United States after searching for her from Russia to Alaska, eventually ending up in Des Moines, Iowa.
Jacob Styne and his men have tracked Charlie Bradbury and the Book of the Damned to Iowa, when Jacob and his man think they have Charlie cornered, they are caught off guard when Charlie goes on the offensive, killing one of Jacob's men and slashing his hand with a sword. When Charlie questions why he is following her, he tells her he isn't, he's following the Book of the Damned. Telling her the book belongs to his family, and that she can kill him, but it won't stop the rest of his family from coming after the book. When Charlie gets distracted by Jacob's tattoo, he takes the moment to knock the sword from her hand and retrieve his gun. As Charlie makes her escape, Jacob is able to wound her, however the shot wasn't enough and Charlie slips away once again.
Using a special compass to track the book, Jacob reaches a dead end when he realizes that Charlie has figured out a way to hide the book. He orders his men to search up and down the stretch of highway the compass lead them to, to see if anyone has seen her.
Jacob makes his way to a convenience store, where he proceeded to kill the clerk before Dean Winchester arrived. As Dean buys some food, Jacob pretends to be a clerk, however Dean gets a look at his family crest tattoo and pulls his gun on Jacob. Jacob is able to get Dean off-balance which allowed for his man to restrain him. Jacob tells Dean that is must be providence that a man with the Mark of Cain just so happened to walk in the store where he is at. He tells Dean that the book can remove his "gift" but messing with it will do more harm then good, and Dean she just give it to him. Dean agrees to tell them, and as Jacob comes closer to hear what he has to say, Dean wrestles out of the henchman's grasp and goes for his gun, empty his clip into the henchman as Jacob makes his escape.
Together with two more of his men, Jacob tracks Dean down to Bobby's cabin. He sends the men in first, who attack Charlie and Dean, one is killed by Charlie and the other knocked out by Dean. As Sam is about the burn the Book of the Damned in a holy oil fire, Jacob bursts through the front door. Dean dives for his gun and fires at Jacob twice, hitting him in the chest. Jacob is unfazed and continues to advance on Sam, as Dean fires three more shots into Jacob, to no avail. Jacob notices Sam burns another book instead of the Book of the Damned, and as he reaches him and begins to choke Sam, Sam stabs him in the gut with a knife. Before Jacob finally dies, he tells Sam that his family will not stop looking for the book.