The Raid on Richard Roman Enterprises was a raid conducted by the Winchesters, Bobby Singer and Charlie Bradbury on Richard Roman Enterprises to retrieve Frank Deveraux's hard drive and hack into Dick Roman's email.



While trying to win the civil war he was in with the archangel Raphael, the angel Castiel took in all of the souls of Purgatory and while he eventually sent them back, he unwittingly unleashed the Leviathans upon the Earth.[1][2][3] The Leviathan leader took on the form of businessman Dick Roman and the Leviathans began working on engineering humanity into the perfect, never-ending food source. During an attempt to learn of the Leviathan plan, hunter Bobby Singer was shot in the head[4] and eventually died of his wounds,[5] choosing to stay behind and become a ghost in order to continue to help the Winchesters in their fight with Dick Roman and the Leviathans.[6]

Following the unleashing of the Leviathan upon the Earth, the Winchesters worked to find a way to stop them, ultimately only finding a way to defeat them, but not kill them with the help of Jody Mills.[7] After receiving a series of numbers from the dying Bobby, Dean turns to computer expert Frank Deveraux for help decoding them and keeping an eye on Dick Roman.[8] Shortly before Frank is apparently killed, he informs Dean that Dick is funding an archeological dig[9] and Dean later finds a report that Dick is funding another archeological dig, making the Winchesters realize that he is looking for something but leaving them unsure of what.[10]


The Winchesters attempt to make sense of Dick's funding of archeological dig sites, but nobody can find a pattern to the sites he's funding and Dean can't find anything in the local lore for any of the sites for fifty miles in any direction that could point to what can be found there that Dick's so interested in. As the Winchesters discuss the mystery, Bobby's ghost manifests before them and as he doesn't know how long he has until he runs out of energy and can't manifest to them again for a while, he starts telling them what he knows about Dick's plans. Bobby tells the Winchesters that just before Dick shot him, he got a good look at his big plan and the numbers, which point to an empty lot in Wisconsin, are the location for a state-of-the-art slaughterhouse for humans. Bobby explains that Dick has put something into meat that dumbs humans down and makes them docile for the Leviathans. While Dean tells him they haven't been back to Biggerson's since the fiasco with the Turducken sandwiches,[4] Bobby informs Dean that Dick has now bought a list of restaurants "10 pages long" to sell his contaminated meat. Bobby tells them that the next step in Dick's plan is to cure humanity of all the diseases that afflict humans in order to engineer the perfect herd for the Leviathans to feed on forever. Bobby warns them that while they've dealt with monsters in the past that like to eat people, they have nothing on the Leviathans who plan to take humanity's spot at the top of the food chain and rule the Earth with humanity as their food.

Arriving to work at Richard Roman Enterprises, Charlie Bradbury is pulled aside by her boss Pete for a meeting with Dick Roman. Dick tells her that he has big plans and he doesn't want the actions of "one tiny little person" to jeopardize those plans. Charlie panics, thinking Dick is talking about her hacking super PACs and transferring money, but he is simply amused by her actions. Dick tells Charlie that she has a certain "spark" that makes her impossible to copy and asks her to hack the hard drive he got from Frank Deveraux and bring the results to him, telling her she has three days to do it in or she's fired.

As Charlie hacks Frank's hard drive, it automatically sends an email to Sam, warning him of the hack and that the hard drive has important information on it about them such as their new aliases, their hangouts and where they've stored the Impala. Frank's email warns them that while he's encrypted the drive well, they should expect someone to break it eventually so he installed a tracking device on the hard drive. Checking the tracking device, the Winchesters are left worried when they discover that its at Richard Roman Enterprises. Bobby suggests that they mail in his flask which will allow his ghost to infiltrate the premises, but Sam and Dean refuse as its Dick's office and if Bobby sees Dick himself, he could turn into a vengeful spirit, something that there is no return from.

Charlie begins attempting to hack Frank's hard drive with no luck, instead crashing her computer when she apparently gets close thanks to a War Games rip-off that turns out to be a joke from Frank and a trap. After around a day of non-stop work, Charlie finally manages to succeed in hacking Frank's hard drive and is drawn to Frank's file on Richard Roman Enterprises and decides to read it despite Dick ordering her to bring the hard drive straight to him once she'd hacked it. Reading Frank's files, Charlie learns what Frank knows about the Leviathans, but just believes that Frank is crazy and goes to find Pete to give him the hard drive. Finding Pete in the garage about to smoke, she witnesses Dick having a Leviathan named Tarrell take on Pete's form and then eat him in order to replace Pete so that he can keep a closer eye on Charlie as she hacks the hard drive. Realizing that Frank is not crazy but right, Charlie flees the building without the hard drive.

Reaching her apartment, Charlie begins to pack and makes up a lie to Pete about why she left so early when he calls her, but realizes she is not alone and attacks Sam and Dean who are waiting for her with a plastic sword, believing them to be Leviathans. Dean tells her they are not Leviathans and after confirming that Charlie knows what borax does to Leviathans, the Winchesters and Charlie splash themselves with some borax to prove that they are humans. Sam and Dean explain the situation to Charlie and that they found her as Frank's hard drive hacked her web cam and sent them video footage of her. While annoyed by this, Charlie is also impressed that Frank thought to do so. Sam asks Charlie how long it took her to hack the hard drive and when she tells him that it only took her a day or so and that so far there's nothing that she can't hack into, Sam asks her if she could hack into Dick Roman's email. After the Winchesters inform her that Dick is the Leviathan leader and that the Leviathans plan to turn humanity into their food source, Charlie agrees to hack Dick's email. Dean tells her to look for anything on archeological dig sites as they need to know what Dick is up to, but Charlie discovers that she can't hack Dick's email as its on a private server in his office not the company server. The only way they can access his email is with Dick's phone or from his computer in his office. While Charlie, the only one who has the skills to hack Dick's email initially refuses to break into Dick's office to do it, she realizes that she can't go back to her old life now that she's seen everything on Frank's drive and Dick will kill her for it. Charlie reluctantly agrees to help them by erasing Frank's hard drive and breaking into Dick's office to get at his email in hopes it will help them find a way to defeat the Leviathans. With Charlie now on their side, the Winchesters sit down with her to plan their raid while Bobby watches from nearby, invisible.

That night, the Winchesters station themselves outside Richard Roman Enterprises in a van with Charlie's laptop to put the security camera footage on a prerecorded loop for her on her signal. Charlie set her computer up for a fifteen-minute loop, telling them that if it takes her longer than fifteen minutes to hack Dick's computer, she deserves to get eaten. Dean spots Bobby's flask in Charlie's bag on the security cameras and they realize that Bobby put it there so he could follow her inside even after they told him to stay outside. Unwilling to call off the raid as they will only get one chance at it, Dean contacts Charlie who is wearing a Bluetooth headset to keep in contact with him and tells her to take care of the flask, calling it a family heirloom. Charlie panics for a moment about actually going through with their plan, but Sam convinces her to go by reminding her of what Hermione from Harry Potter would do. Emboldened, Charlie enters the building and rides the elevator to the fourth floor where her desk is. Once she gets there, Sam activates the prerecorded loop of an empty elevator and Charlie switches the backing of her security pass for that of another and rides the elevator up to the eleventh floor where Dick's office is.

While the looped footage tricks the security guard in the lobby, Charlie finds another one guarding the eleventh floor and not looking like he's planning on leaving soon. After learning that the guard has shown signs of being attracted to Charlie when he sees her at work everyday, Dean tells Charlie she will have to flirt her way past him. However, Charlie tells Dean she can't do that as she's a lesbian and doesn't know how to flirt with men. Dean decides to talk her through flirting with the guard, Bill and while he succeeds, Sam is left highly amused and Charlie repeats everything he says including the parts that are not flirting, nearly ruining the effectiveness of the tactic. However, it ultimately works and Bill agrees to let Charlie use the executive bathroom rather than the downstairs one. Once she's past Bill, Charlie slips into Dick Roman's office and begins hacking his computer. Charlie quickly breaks Dick's password and begins copying Dick's emails onto a flash drive, but her being gone so long draws Bill's suspicions and he goes to check on Charlie. To buy her time, Bobby closes the door to Dick's office and locks it, buying Charlie time to get into Dick's bathroom before Bill can get into the office. Bill goes into the office and nearly leaves when he doesn't see Charlie, but stops when he spots her purse on Dick's desk. Seeing this, Charlie emerges from the bathroom and claims that she misunderstood Bill's directions and got the wrong door. To buy herself more time, Charlie gets a pen from Dick's desk and uses it to give Bill her phone number. Afterwards, seeing that the download is complete, Charlie removes her flash drive and returns to her desk to check what she got from Dick's computer and to erase Frank's hard drive.

Reaching her desk, Charlie sends the Winchesters all of the emails she got off of Dick's computer about the archeological dig sites. At that moment, Pete comes in to check on her progress and Charlie promises to get back to him in a few hours. Pete leaves and as she promised to get to him in a few hours, she decides to stay and finish the job rather than leave and draw suspicion to herself. Reading Dick's emails on the digs, they learn that Dick stopped digging days ago and realize he must've found what he was looking for. Charlie discovers that whatever Dick was looking for was found in Iran and has been moved through armored cars and private planes and will be arriving at a nearby airport for pickup soon. While the Winchesters don't know what it is that Dick wants so badly, they realize that it must be important and decide to intercept the package themselves. Charlie finds that the package will be arriving for pickup in forty-two minutes so Dean asks her to buy them more time. Charlie does so by sending an email to Dick from the travel department stating that the package was delayed due to inclement weather. Charlie then sets to work on erasing Frank's hard drive before she will flee the building.

After erasing Frank's hard drive, Charlie gets up to leave, but Dick himself arrives to check on her progress before she can get very far. Charlie tells Dick she didn't find anything about his company on the hard drive and due to her deleting it, nothing comes up when she does a search on Sam and Dean Winchester. While Dick talks to Charlie, Bobby watches and tries to keep control of himself due to his anger at Dick murdering him. After finding no results on the Winchester search, Dick asks if they could still find the files even if they were deleted, but Charlie tells him she can't if they were deleted well. Disappointed, Dick asks her how she hacked the hard drive since it was supposedly unbreakable, trying to understand her "spark" that makes her so special. Charlie just tells him that nothing's safe if you keep at it long enough which Dick likes and expresses disappointment that he can't clone her. Before he can question her further, Victor contacts him to let Dick know he has the package. Dick leaves to meet with Victor and Charlie quickly flees.

At the airport, Sam and Dean, disguised as baggage handlers, are able to get the package before the Leviathan Dick sent to pick it up, Victor. Instead, Victor gets a suitcase with a borax bomb in it. Sam and Dean are confused by the block of clay inside their stolen suitcase, but decide to figure it out later. When Dick opens the suitcase Sam and Dean left for him, the borax bomb goes off, injuring both Dick and Victor. Dick, who recovers quickly, realizes that Charlie betrayed him and orders the building locked down.

Charlie reaches the exit only to find it locked down on Dick's order. Bobby quickly freezes the glass, causing it shatter, but not break out of the frame. Pete goes after Charlie while Bobby goes after Dick. On his way to Dick, Bobby shoves Pete out of his way, sending Pete crashing into Charlie, breaking her arm. As Sam and Dean break in and knock out the human security guard and douse Pete in borax, Bobby attacks Dick, throwing him into a cabinet. Bobby briefly becomes visible and attacks an amused Dick every time he tries to get up, but is unable to keep Dick down for long. Knowing they can't defeat Dick now, Sam and Dean flee with Charlie and Bobby, leaving an enraged Dick behind.

Driving away from Richard Roman Enterprises, Charlie tells them she is not okay as Bobby's attack broke her arm. When Charlie questions why they didn't just kill Dick, Sam informs her that they can't yet but that they will before she passes out from the pain.

Dick returns to his office, calling another Leviathan on the phone and demanding that they retrieve the suitcase before the Winchesters figure it out. A recovered Victor begs Dick not to bib him, but Dick tells him he's not going to bib him and waste a perfectly good meal. Dick eats Victor for his failure, killing him.[11]


With Charlie now in danger for helping them, Sam and Dean get her medical treatment and then send her away to start a new life on a bus. Charlie tells them that its not the first time she's disappeared and not to contact her again[11] though she leaves them a way to hack into SucroCorp's security system.[12] Despite Charlie's request, Sam and Dean later encounter her while doing a case around a year and a half later, Charlie having come out of hiding once Dick was dead and Richard Roman Enterprises went bankrupt.[13] Following that encounter, Charlie starts to keep in touch with and aid the Winchesters and becomes a hunter herself.[14]

Following Bobby hurting Charlie while trying to stop Dick, the Winchesters become concerned that he is starting to show signs of becoming a vengeful spirit which he can't return from.[11] Their fears end up realized when Bobby becomes a full-fledged vengeful spirit and goes after Dick, forcing them to put him to rest.[12][15]

While the Winchesters initially have no idea what's in the package they stole from Dick, they discover that its the Leviathan Tablet with help from Castiel and Kevin Tran and that it contains information on how to stop the Leviathans.[16] Using the information from the Leviathan tablet, the Winchesters are able to create a weapon capable of killing a Leviathan and use it to kill Dick Roman, effectively defeating the Leviathans.[12]


  • Introduction of Charlie Bradbury who later becomes an important ally of the Winchesters.
  • First signs of Bobby starting to become a vengeful spirit as Sam and Dean feared.
  • Introduction of the Word of God tablets, an important plot point in the coming seasons though the Leviathan tablet isn't seen outside of its clay casing until Reading Is Fundamental.
  • Charlie comments that the really evil bad guys always need "a special sword" to kill them. This proves to be prophetic as the Winchesters end up having to create a special weapon to kill Dick Roman and defeat the Leviathans. The package they stole from Dick during the raid contains the Leviathan tablet which contains the instructions for such a weapon. There are also other occasions where "a special sword" is required like Charlie said such as with the First Blade and Abaddon.
  • While Dick uses Richard Roman Enterprises as his headquarters during the raid, he soon moves to SucroCorp where the final battle with the Leviathans takes place. During the episode the raid takes place in, a SucroCorp ad is shown and its mentioned in the following episodes though it isn't actually seen until There Will Be Blood and Survival of the Fittest.


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