Why me?

Arrow/Supernatural Crossover

Chapter 1 - Reconnections and Revelations

Oliver was engaged in a firefight. He had chased down some Triad members who were in town. Apparently there was a bidding process going on for the contract to kill the new district attorney. Several of the criminal elite in Starling were looking for a good assassin. The more he found out about the criminal element and how it worked the more he realized it ran just like the government. The irony of his mother running for mayor grew stronger every day.

He ducked and rolled as bullets came flying from his right. He found some shadows to hide in to try to get a line of sight on the gunmen. He sensed a presence on his left., he spun and saw a man that looked completely out of place standing there. He was in a beige trenchcoat, a blue tie, suit coat and slacks. He had short wavy black hair and an odd expression on his face. He was also completely exposed to the gunfire.

"Are you insane?" Oliver yelled as he dove forward to push the man down. When he connected it felt like he had run into a granite cliff. The man did not move a step.

"No. I'm an angel."

Oliver felt a hand on his shoulder then came the strangest sensation. He felt like he was traveling at an incredibly high speed. He swore he saw the planet Earth from space then everything stopped and he was in the middle of a different firefight.

"What the hell? " Oliver swore as he ducked down and tried to get his bearings. Instead of a dark alley in Starling City he was outside of an abandoned farmhouse.

"Cas! Really? " he heard a familiar voice. A voice that he shouldn't be hearing.

"Dean, you need help. I have to find Sam and you can't do this alone. So I brought him." the man with the trenchcoat replied.

"Dean?" Oliver said, stunned. "Wait weren't you in..."

'Yes." Dean interrupted.

"How'd you get.." Oliver started again

'Him." Dean pointed at the man in the coat.

"Who are…" Oliver went for a third question

"Castiel. I am an angel of the Lord. I pulled Dean out of hell."

"Am I going to get to…"

"No. We're busy Oliver. Ask later. " Dean cut him off and started firing a shotgun at something.

"Care to at least clue me in on who's shooting at us? " Oliver snapped.

"Who do you think?" Dean retorted

"Ok. Well I am not equipped to to shoot demons. I left the salt in my other suit. " Oliver ducked as a bullet ricocheted off a rock.

"Here." Dean threw Oliver a shotgun . " Aim it that direction and pull the little trigger thingy. Sorry it's newer technology."

"Dean. " Castiel said in a scolding tone. He crouched down next to Oliver. "Sam Winchester is missing and we are trying to get an artifact out of the hands of the demons that are in that house. Lucifer has been raising the Four Horsemen and he needs Pestilence and Famine. We stopped War once, Death got out. "

"Lucifer?" Oliver asked incredulously as he aimed the shotgun and blew a demon's face off. "What happened?"

"Hey you can shoot a gun. Why do you use arrows? " Dean asked

'Why do you drive a 67 Impala?" Oliver replied. Dean looked at him, cocked his head to the side, nodded a bit and kept shooting.

"Touche." Dean smirked.

"It's a long story Oliver Queen. Dean and Sam are part of a plan to end the world. "Castiel replied. "They are fighting their destinies though. Sam disappeared and I have to find him before things get worse. You have to help Dean. " then Castiel vanished.

"What? Why me? " Oliver said. "This is not my area of expertise."

"Damn it Cas! " Dean snarled. " Could he have brought me another hunter? No. He brings me someone who has no idea what's going on. " Dean snapped another shot off. "Ok, so short version. As Cas said we have to get into that house. There are some bones from some genocide that Lucifer needs to let Famine out. Sam disappeared three days ago. For all we know Lucifer took him somewhere. Cas has to focus on that so I get to do this and apparently you have been drafted to help. "

Oliver was trying to process as fast as he could. Lucifer? Famine? He shook his head. " Focus on the people shooting at you" he thought to himself.

"Ok, tell me the rest later. " Oliver said. He snuck a look around the rock he was crouched behind. He counted 5 demons outside all blocking the entrance to the house.

"Do you know how many are inside? " He asked Dean.

"Cas said about 4 more in the house." Dean replied

"Wait this Castiel, he's an angel. Can't he just send these demons back to wherever?" Oliver asked.

"Yeah, not so much. He's disobeying orders so he's gotten cut off from a lot of his power. Heaven really dislikes independent thought." Dean said.

"Alright. Well there goes that idea. " Oliver replied. He peeked around the rock again and looked for other access points.

"You wouldn't happen to have more of those pumper trucks?" Dean asked hopefully.

"They, like the salt are in my other suit." Oliver replied dryly "Are we on a deadline? " Oliver asked.

"Not really. We just need to get the bones away from the demons as soon as we can. I think the demons are still looking for them seeing as how they haven't disappeared. There's always the other possibility that's it a trap. It usually is. "

"If it's a trap why do you keep falling for it?" Oliver pointed out. Dean shot him a glare.

"They know we know that they need these things. So when they find one they always try to trap or kill us when we come to take it away. We're not complete idiots. " Dean snarled.

As they had been talking Oliver had continued to scan the area. It was a scrubby grassland type area, not a lot of cover. There were a few trees close to the house. His eyes mapped a path from where he was to the trees. If he had enough of a distraction he could probably make it.

"Dean, I have an idea but I will need a distraction. If I can make it to those trees I can hop on the roof of the house and create an access point. Do you have a shotgun with a strap I can throw over my back, I'll need both hands. " Oliver asked.

"Yup. " Dean passed him a sawed off shotgun, a box of shells and a flask. "Holy water in there. Dip your arrows in it. It should work. What's the plan? "

"I'm going to climb those trees, use one of my exploding arrows to make a nice hole in the roof, shoot through it, in theory kill the demons inside. Then jump into the house and bust out a window. You and I can grind the remaining ones up in between us. " Oliver said.

"Great idea, except that if one of them throws you off the roof you'll be stuck right in the middle of all of them." Dean pointed out.

"Other options?" Oliver snarled.

"Don't have any. Just thought I'd point that out. " Dean replied. "So when do you need that distraction? "

"Now." Oliver said and he started running, crouched low, along the path that he had plotted out in his mind.

"Great. " Dean said. He stood up started firing shots into the crowd of demons and ran the opposite direction of Oliver. He waited until the shotgun clicked on empty.

"Awww out of bullets Dean?" He heard one of the demons say. Dean didn't have to try too hard to act nervous.

"Well, like you guys always say. I'm the moron." Dean replied. He watched as the 4 remaining demons walked slowly up to him. Oliver had actually killed one with the shotgun earlier. Dean had placed himself next to another rock and a tree he could duck behind. He just had to wait. He saw Oliver ghosting from rock to rock behind the demons moving as fast as he could. Dean moved his eyes back to the demons so they wouldn't get suspicious.

"It's so cute you try to fight us without Sam around. He's really your only protection against us. Daddy doesn't want Sam to get accidentally hurt when we rip you to shreds." Another demon spoke.

"Well that's touching. " Dean retorted. They were almost close enough. He flicked his eyes to the trees and saw Oliver jumping from the tree and landing on the roof of the house. "Now or never." Dean thought.

Dean yanked the Colt out from his waistband and fired as fast as he could. He took out 2 of the demons then heard an explosion from the roof. One of the demons flicked a hand and Dean got flung back into a tree. He managed to keep a hold of the Colt and fired as he landed. He missed but Oliver didn't. One demon yelled and black smoke came out of his mouth. As he fell forward Dean saw an arrow sticking out of the demon's back. Dean pointed the Colt at the remaining demon it vanished. Dean got up and ran to the house. He saw Oliver firing the shotgun into the hole on the roof. Oliver went flying backwards and barely caught the edge of the roof as he went over it, managing to save himself from a full story fall. Oliver dropped down, shot the window he landed in front of out with the shotgun, threw the now empty shotgun down and started shooting arrows.

"Dean, there's a bit more than four in there. Try six." He shouted as Dean headed to the door. Dean changed his direction and headed towards Oliver who was ducking and running to the door out of the line of fire of the demons.
"Here. Sam said you're damn good with a knife. " Dean tossed him Ruby's knife, Oliver caught it. Dean reloaded the Colt and ran to the window. 'Count of 3. I'll cover you." Dean said.

'Wait a knife? " Oliver replied.

"Kills demons one hit. Now go." Dean snapped.

"And you made fun of my arrows? " Oliver retorted. Dean glared at him. Oliver ran to the door and looked at Dean.

"1, 2, 3!" Dean shouted as he ran around in front of the window and started firing the Colt into the room. Oliver kicked down the door hoping Dean wouldn't shoot him by mistake. As he burst into the room he saw 6, no wait 5, demons standing in front of him. Dean had nailed one as Oliver had burst through the door. Three were looking at him the other two were shooting at Dean. Oliver gripped the knife, took three steps and sliced at the first demon. He barely connected with the demon's arm who screamed and dropped. Oliver didn't stop moving. He spun to his right and ducked as the second demon fired a shot. Oliver's arm cut lengthwise across the demon's stomach, she started screaming and dropped to the ground. Dean had taken out another one with the Colt and the remaining two looked behind Oliver and just vanished. Oliver heard a step from behind him and saw an older gentleman standing there. He put his hands up.

"Stop, don't stab." he said with a superior look on his face and a bit of an accent. "I'm Crowley. Dean knows me. The bones are behind that wall. " He said as he pointed to a wall to the left of Oliver. "Behind the copy of "The Scream" painting. Oddly appropriate. Those others won't be back for awhile. You're welcome. " then he vanished. Oliver was really getting sick of people vanishing into thin air.

"Thank you, you SOB." Dean said into the thin air. Then he walked over to the framed print of "The Scream" pulled it off the wall and started tapping the wall to find a hollow spot. Once he found it he looked took the Colt by the barrel and slammed the butt of it into the wall. The wall cracked and splintered and eventually Dean had created a decent sized hole in the wall. Dean reached in and pulled out a bag, he opened it, grimaced and closed the bag back up. "Yeah this is what we needed." He tucked the bag into his jacket and started walking out the front door.

"Alright Oliver, let's see if we can get you home. Sorry for all of this." Dean said as Oliver caught up with him.

"Here's your knife back. " Oliver said.

"Thanks I'll probably need that later. C'mon, the Impala isn't too far from here. " Dean started walking up the gravel driveway. Oliver pulled his phone out and saw he had minimal reception.

"Dean. Where are we? I should probably text Felicity and let her know I'm ok since she tracks me. She's probably in full blown panic right about now.. " Oliver asked

"We're about 50 miles outside of Billings, Montana. I am heading to Wyoming but I can drop you off at Billings if you want to catch a flight. " Dean replied.

"Dean, look at me. " Oliver stopped and waited for Dean to turn around

"Oh. " Dean looked and finally realized that Oliver was in his vigilante attire. "Don't suppose you have a series of books being written about your life and people go to conventions dressed like you dress and acting like you act? If so you can just say you're going to one of those. "

"Not that I am aware of. Who'd want to dress like me anyway? "Oliver replied.

"You're lucky. Trust me. It's creepy. Well you'd probably fit some of my spare clothes. We're about the same size. You can just mail them back to me when you get home. "

"Dean. " Oliver heard a voice from behind him. He spun around and had an arrow nocked before he realized it was Castiel. This was going to give him a heart attack if it kept up.

"What Cas? " Dean replied. His voice nonchalant as if this happened all the time.

"I found Sam. I can't get him out though. " Castiel said, his tone concerned.

"Why?" Dean's voice had grown harsh.

"Lucifer has him. " Castiel says.

"What do you mean has him? Sam said yes?"

"No. Sorry I'll rephrase. He has him in a trap. He's showing him realities without you in them. He's trying to break the bond between the two of you. Lucifer knows the only reason Sam hasn't said yes is because of his love for you. If he can break that or make Sam give up hope he knows Sam will accept him." Castiel said. Oliver noticed that Castiel's voice was oddly emotionless.

"Fuck! Where is he? " Dean said.

"Ohio. I can't take both of you. I'm losing too much power. I need to have some to help you with Lucifer. " Castiel said

"Oliver isn't part of this. Take me. " Dean said. He sounded as if he was ordering Castiel. Oliver saw something cross the angel's face. Some hint of expression.

"No. I can't take you and all your gear. Lucifer isn't leaving Sam unguarded. " then he looked at Oliver. Oliver felt like the angel was reading his entire life history directly from his mind. His gaze was piercing. He had never felt so emotionally exposed in front of someone, it was incredibly uncomfortable for him.

"Oliver Queen. I need to speak to you. Dean. Wait here. Come with me Oliver." Castiel turned and started to walk away.

"Cas, we don't have time for this shit. " Dean snarled. Castiel turned and looked at Dean. Something in his posture gave the impression that he was silently challenging Dean. Dean winced and backed down. "Fine." Dean turned and walked to the house, fierce anger evident in every step. Oliver hadn't spent a lot of time with Dean but he knew Dean didn't back down from many people.

Oliver took a few steps and caught up with Castiel. They started walking, Castiel's face was pensive and troubled.

"Oliver. I didn't choose you at random to help Dean today. You helped Sam after Dean was taken to hell in fulfillment of his contract. " the angel paused as if searching for the words. "I find that I no longer am certain of anything in this world on in heaven. Sam and Dean fighting their destinies, demons rebelling against Lucifer, angels acting like demons. Nothing is clear anymore. "

"Castiel, I wasn't much of a church goer growing up so I am not really clear on all of this. " Oliver said.

"Yes, I suppose this is a bit overwhelming. I tend to forget most humans are not as informed as the Winchester's. As Dean says, long story short. Sam and Dean are the vessels for Lucifer and the Archangel Michael respectively. Vessels means that they are the ones destined to be possessed by the two to fight for dominion of this world. In this case the brothers have to give their permission to be possessed. Angels can't just jump in and take over a human like demons can and Lucifer is still technically an angel. The brothers are refusing. However it's a bit more complicated than that. You see the brothers also caused Apocalypse to start and freed Lucifer. This was also part of their destiny. When Dean broke in hell and started torturing seals it opened the first seal to let Lucifer out of his cage. When Sam killed Lillith he broke the last seal. "

"Wait. Back up" Oliver said. " Dean broke? He wasn't gone that long." Oliver said.

"Time in hell runs differently. To Dean it wasn't a few months. It was 40 years. He was tortured every day for 30 years then for 10 years he tortured others. He was a righteous man who shed blood in hell, thus opening the first seal. " Castiel said with his eyes full of sorrow.

"Why didn't heaven save him earlier?" Oliver asked, horrified at what Castiel had said.

"Heaven is not what you may think. I am coming to believe that God is either dead or not interested in this world or the end of it. I wasn't ordered to save him until after he gave in. I know the angels above me knew about it well before before they told me to save him. We all knew when he had been taken to hell, the demon's screams of triumph told us. " Castiel looked away from Oliver, frustration and shame on his face. "We lost track of Sam. I think some demons were concealing him without his knowledge. It appears that you helped him deal with Dean's apparent death but.."

"But what?" Oliver was almost afraid to find out. He had hoped when Sam left Starling that he would be able to stand on his own. It didn't sound as if that had been the case.
"There was a female demon named Ruby." Castiel said.

"We met. She warned us of the trap in Starling the first time I met the brothers."

"Yes, very helpful she was. She helped Sam to become stronger by using the demon powers that Azazel imparted in him as an infant. She helped Sam become addicted to demon blood and then manipulated Sam into freeing Lucifer. " Castiel's face and voice had grown colder and colder as he spoke. "Sam was trying to compensate for Dean not being alive. Ruby showed him a "safer" way to exorcise demons where the human was not hurt and told him that he would eventually be strong enough to kill Lillith, the original demon, she who killed Dean. I brought Dean back before Sam freed Lucifer. Unfortunately, Sam and Dean had a falling out and Sam chose Ruby over Dean. "

Oliver stopped moving he was so stunned. "Why would Sam do that?" he couldn't believe it.

"I have a hard time understanding the complexities of human emotions. Angels aren't allowed to have emotions. Emotions are what caused the original rift between Lucifer, Michael and God. " Castiel said, his voice was empty but his eyes were not.

"You have emotions though." Oliver said quietly.

"Yes. They are what have been influencing my choices. I think my choices have been correct though. I dislike seeing humans as merely pawns, pieces to be moved around by others. It's not right. These complex emotions that the brothers have. They are why I picked you to help Dean today. " Castiel stopped and looked directly at Oliver. Oliver found himself almost squirming under the intensity of his gaze. "Dean needs to forgive Sam and himself. Lucifer manipulates with the truth, he uses the weakness of human emotions to convince people to do his bidding. Lucifer never lies, he doesn't need to. He merely exposes a human's insecurities and fears then reinforces them. Sam has a great many insecurities and so does Dean. They both know Sam has betrayed Dean once and Dean expects Sam to do it again. So does Sam. Dean spends many hours condemning himself for breaking in hell. His father lasted longer in hell and never broke, Dean sees himself as less than his father. I don't have the words to get through to them. " Castiel said.

"I think you have the words. You just explained their innermost thoughts to me." Oliver pointed out.

"There's a great difference between explaining their emotions and getting them to face them. You and your followers, Felicity Smoak and John Diggle. The three of you got through to Sam. If he had stayed with you longer I think he would not have fallen to Ruby." Castiel said.

"Castiel, Sam was a wreck when I found him. He was out of control and in a place where he was somewhat willing to listen. I don't know Dean all that well but it seems stubbornness is one of his strongest traits. "

"Yes, that is true." Castiel agreed. "That stubbornness has been the only thing that has kept the world from ending. Understand Oliver, they are on the precipice of their ability to fight Michael and Lucifer. If Sam accepts Lucifer, Dean will be forced to accept Michael. "

"To what end. What is the point of it all? " Oliver asked. As soon as he saw the immense amount of sorrow in Castiel's face he instantly regretted asking the question.

"Lucifer and Michael will fight to the death. They will be doing it using Sam and Dean's bodies. Sam and Dean will be aware the whole time. One of them will kill the other." Oliver stopped and leaned against a tree to catch his balance as the immensity of what Castiel had told him sunk in.

"What a sadistic bunch of bastards! These are angels who are doing this?" Oliver's voice crackled with anger.

"Yes. " Castiel said.

"Who's idea was this anyway?"

"God's." Castiel's voice was empty.

"Well fuck that and fuck God. " Oliver snapped. "I still don't understand how I can help."

"You are stubborn, like Dean. You have been tortured, like Dean. In your own way you became evil. You have killed, you have tortured others. Even if it wasn't physical torture you used fear as a weapon to get people to do what you wanted which is a form of torture. On some level you have enjoyed it. You understand loss and betrayal, you understand rage and you understand forgiveness. You understand feeling like you are less than your father. You also understand happiness and a "normal" life like Sam. You have in some measure forgiven yourself for what you have done. You choose not to kill anymore which shows that you have reclaimed some of your humanity. Oliver Queen, you are both Sam and Dean in one person. Dean will listen to you. He must. If he goes to where Sam is and doubts Sam, Sam will know it and he will give in to Lucifer. You have to get through to him like you did Sam. " Castiel stopped and just stared at Oliver. Oliver realized that this angel, this powerful being was begging him for help. He was also incredibly unnerved at what Castiel had said. The angel had seen the depths of his soul in a way no one, including himself, had.

"I...I don't know what to say. I wouldn't even know how to start this conversation with Dean. " Oliver admitted.

"Dean is ready to talk. He just hates to. Maybe buy copious amounts of alcohol. It seems to be a commonly used tool among humans to release inhibitions. " Castiel quite scientifically pointed out. Oliver was having difficulty keeping up with the switches in Castiel from cold emotionless angel to a being with emotions. He had to chuckle at that last bit though, it reminded him of something Felicity would say. He turned his head and looked at Dean who was leaning against the Impala, impatiently waiting. He really looked at him. Dean was on edge, he was scared and angry. He was trying incredibly hard to conceal it but everything about him radiated fear and hopelessness. If Oliver could see it Sam would and the demons could probably smell it a mile away.

'Dean knows I have money and can fly us to Ohio in a matter of hours. That won't be enough time to talk to him. " Oliver said.

"Dean hates to fly, plus he won't leave the Impala or the weapons. Actually he won't leave the Impala, he really could care less about the weapons. " Castiel replied.

"You want me to ride with Dean for what, 3 or 4 days? I have things to take care of back home."

"It's a 22 hour drive to Ada, Ohio where Sam is.. You can break that up into two days. Dean probably won't let you drive the car. Oliver, if Sam gives in to Lucifer it won't really matter what's going on in Starling City. There won't be a city left for you to save." Castiel pointed out.

"Are you going to overrule his objections? I don't think I will be able to. " Oliver said.

"Yes. Dean owes me in ways that he won't refuse me. Are you choosing to help?" Castiel asked intently.

"As long as I am not selling my soul to someone, then yes. " Oliver said. Castiel looked hurt.

"My brother's may act like demons but I don't. I am still an angel and I still remember what it is we are supposed to do. " Castiel said softly.

"My apologies." Oliver said humbly.

"I forgive you." Castiel's voice was serious. Oliver realized an actual angel was forgiving him. He felt an immense sense of power coming off of Castiel. He realized that there was something more to those words than people understood.

"Thank you." he said, his voice almost awestruck at what he felt. The sense of power faded. Castiel nodded at Oliver, turned away from him and started to walk towards Dean. Oliver followed at a respectful distance behind Castiel. He slowly realized that he was in the presence of something otherworldly that was deserving of immense respect. Even though Castiel was losing his power he was still an angel and not to be trifled with.

'Are we done with the emotional pow-wow? Everyone caught up now? " Dean said, his voice rough with anger and impatience.
"Dean Winchester. Enough. Have I ever done anything that wasn't needed?" Castiel spoke, his tone was filled with steel. Oliver watched as Dean's eyes narrowed. Dean looked from Castiel to Oliver and back.

"You want him to come with me and we're driving. You're not taking me to Sam."

"Correct. " Castiel replied.

"Castiel, Sam is with Lucifer. Have you forgotten his history with demons? " Dean snapped.

'I have not. Have you forgotten that I know Lucifer better than you? If you cannot trust or have faith in your brother Lucifer will use that to destroy the both of you. You need time to reflect and you need Oliver to help you when you get there. "

"Sam is fucking weak Castiel. You know it as well as I do. I have had to keep him on the right path his entire life. It took less than 2 months for him to go darkside after I died. " Dean shouted.

"Sam is not weak Dean. " Oliver said.

'How the fuck would you know?"

"I helped him, after you died. He was far gone. Your death destroyed him, yes. He fought his way back from the brink of suicide. All he thought of was you, he had nightmares of your death. He told us how he had failed you because he couldn't save you from hell. He was shattered. Between your death, Jessica's death and your Dad's death. Think for a minute what he went through. He was living his own life and was as happy as could be. Then it all got ripped away. You were all he had left. Think." Oliver spoke quietly, not wanting to enrage Dean further. Dean closed his eyes.

"Cas. I don't need mental or emotional help. I need to save Sam. " Dean's voice was getting desperate.

"Dean. Look at me. " Castiel said. Dean opened his eyes and looked at Castiel.

"Do you trust me? " Castiel asked. Dean didn't speak a word. Castiel's eyes narrowed. "Of all the angels and demons that have come into your life. I am the only one that has not tortured, threatened, coerced or manipulated either you or Sam. I have earned your trust just as you have earned my trust. Now will you speak the truth or will you deny me. " Dean rocked back as if Castiel had punched him. There was a reference in that statement that Oliver was missing.

"I trust you Castiel. " Dean's eyes were lowered and his shoulders sagged in defeat.

"Good. Oliver will need clothes. Call Felicity Smoak and tell her to get some for you. I will pick them up later today and bring them to you. Oliver is not hidden from angels like you are Dean so I will keep them off of you until you reach Sam. If Sam gets moved or is in further danger I will let you know. " then Castiel vanished.

Dean took a shuddering breath and looked at Oliver. "Let's get you out of that suit. It stands out a bit much during the day." He walked to the back of the Impala, popped the trunk and pulled out a pair of jeans, a shirt and a spare jacket for Oliver. Oliver texted Felicity with an update and told her to get some of his clothes and a cell charger for him. Then he told her not to call right now, that he would call her later and explain further. She sent a simple OK back. She had grown used to unusual requests.

"Dean." Oliver asked as he was changing. "The last thing Castiel said to you, about denying him. It was phrased almost like a Bible quote." He wanted to figure out why Dean had been so affected by it.

"Yeah. Peter denied Christ three times after he was arrested. Peter was one of Christ's most loyal followers until it came down to Christ being crucified, then he disowned him because he was afraid to suffer the same fate as Christ. Basically Cas was calling me out. Castiel has given up everything for us, well me more specifically. Sometimes I forget that. " Dean turned away and headed to the driver's seat of the Impala.

Oliver slid into the passenger seat his mind spinning. Angels, God, Lucifer? He looked over at Dean and wondered how often Dean and Sam had asked the question that was ringing in his mind. Why me?