"I couldn't help but notice that Dean and Sam weren't exactly the Rebels the Garrison described. When Dean was captured, I begged him to tell the Angels what they wanted to know. He, of course, refused. When we reached Heofon, Dean was thrown into prison and tortured. I cannot go into detail of his imprisonment. It was not my place to oversee his torture; I was only able to hear news from other Angels supervising the prison."

"When you say tortured…?" Sam questioned

"Angels tried just about everything. He was beaten, whipped, poisoned, water boarded, just to name a few. Of course they had to avoid extreme measures as to not kill him. They became increasingly frustrated, however, when Dean would not break." Through John's perturbed look over learning some of the details, Castiel could have sworn he saw a small look of pride coming off the leader at his last statement.

"But the Angels were not about to resign their efforts. After three months of fruitless torture, the Angels decided to try something new. They brought in other Rebels that had been captured and began torturing them in front of Dean. These Rebels that were brought in… they were… expendable. They could be tortured in ways Dean couldn't; they could be killed. And all of it took place before Dean's very eyes."

Castiel paused. "It is rumored that Dean broke for the first time in his cell that night.

"They began to alternate the two tactics. One day he would be tortured and the next he would watch it happen to a fellow Rebel. After a week of this, they say they had gotten farther with Dean in that time than they had within the previous three months. It was then that I devised a plan to escape with him."

Castiel walked down the grand hall, too consumed in what he was about to do to admire the elaborate décor the Garrison favored so much within their buildings. So absorbed was he, in fact, that he nearly missed a superior Angel passing by him. Just in time, he moved aside to the wall of the hallway and stood at attention, averting his eyes in the custom sign of respect. His heart rate quickened at the fear that somehow, someway, the superior Angel would know what he was about to do, would confront him about it. He released the breath he didn't realize he was holding when the Angel disappeared around the corner, and he continued on his way to the dungeons. Descending the stairwell, Castiel noticed an immediate change in the atmosphere. All traces of the grand décor had disappeared, replaced by bleak stone walls. The temperature had dropped considerably, and an air of despair filled him. He gagged as the smell of human waste hit his nose, and then took to breathing through his mouth. Absently brushing his pocket, he reassured himself the key to Dean's cell was still in his pocket.

He scanned the cells as he made his way down the row, each prisoner looking as pitiful as the last. Some of the prisoners were worse off than the others however; not all prisoners were tortured for information, only the important ones. Reaching the storage room, he quickly grabbed a vile of antidote from off the shelf. He took a sheet of linen cloth and threw it over a cart, and then began to place random torture devices off the shelves onto it. Rolling the cart out of the storage room, he made his way to Dean's cell.

When he finally reached it, he grimaced. Dean looked worse than he had thought he would; and he prepared himself. He pushed the key into the door and slid into the small cell. Dean was sitting on the ground against the wall, his arms chained above his head. Castiel kneeled next to Dean and shook him slightly.

"Dean" he whispered in an attempt to wake him. "Dean, wake up. Dean."

Dean jerked slightly upon his awakening, rustling the chains keeping his hands suspended above him. It seemed to take him a moment before his eyes adjusted and recognition set in.

"Cast-" Dean began, but Castiel threw a hand up to Dean's mouth to silence him. He internally cringed at how raw Dean's voice sounded, but there was no time to dwell on such details.

"Dean listen to me very closely," he whispered urgently. "I'm going to get you out of here. But you must do exactly as I say. Understand?"

Dean merely stared at him. Castiel thought he was still half-way out of it when he recognized the look on Dean's face. He was being scrutinized. There was no time for that.

"Dean, do you understand me?" he asserted. Dean looked at him for another moment before nodding in agreement. Castiel removed his hand from the Rebel's mouth and unlocked the chains keeping him against the wall. Dean let out a grunt as his arms fell to his side, but Castiel gave him no time to recuperate. He helped hoist Dean to his feet, and the pair stumbled over to the cart. Dean stopped short when he saw the items on top of the cart.

"You have to trust me Dean." He lifted the linen cloth to reveal a small space underneath. "Hide under here and don't make a sound. I will tell you when it is safe for you to come out." Dean's eyes flashed between the weapons on the cart to Castiel, then finally crouched and fit himself into the cart with Castiel's help.

He rolled the cart toward the dungeon exit, his heart beating a thousand times per minute. Forcing himself to calm, he exited the prison.

"Castiel."

He froze and turned to the Angel guarding the door to the prison. The other Angel looked to his cart and then back up to Castiel.

"What were you doing inside the prison? And what reason do you have for removing its weapons?"

"Jeremiah was unable to sustain his responsibilities for the day, so I offered to take his post." And by 'unable to sustain his responsibilities', he really meant Jeremiah was currently unconscious in a closet. "As for the weapons, Uriel has ordered me to bring these to him."

"Why must he have them?"

"I did not question his order," Castiel snapped. This Angel was equal to his rank. "If you wish to know his reasons, you can ask him yourself," he finished coldly. The Angel's eyes widened briefly at the mere thought of it, then he cleared his throat.

"That will not be necessary. You may continue."

Castiel rolled the cart away, shooting the guard a cold look as if to strongly disapprove his mere mention of questioning an order. He turned around the corner into an alley. Looking around to make sure he was alone, Castiel lifted the linen cloth.

"We're outside the prison. Dean, you have to stay here while I locate the shipment we will use to smuggle you out in. Stay here and remain hidden," he asserted, helping Dean out of the cart. If anyone identified Dean outside, the results could be disastrous. He led Dean over to behind a stack of barrels and lowered Dean down to sit on the cobblestone street.

"Stay here. Got it." Dean grunted back weakly. His breathing was labored; all the movement was clearly causing him pain.

Castiel nodded and moved out of the alley. He would have to move quickly. He didn't think anyone would have business in that ally for some time, but if someone were to wander there by happenstance... He didn't even want to think about it. His eyes scanned the streets as he strode down them. There was no need to worry if he stood out among the masses; every Garrison member within the city moved with purpose. There was no one walking through Heofon at a nice leisurely pace, enjoying the view. Everyone here had a purpose and if they were not fulfilling that purpose they were soon replaced with someone who was. The entire Garrison operated like a well-oiled machine.

Finally, Castiel found his mark. A trailer, tied to a horse, was being loaded with supplies to be taken out of the city. Castiel watched their progress until the last item was loaded onto the trailer. The workers then began to put the tarp over the supplies to protect them from the environment. Castiel turned and retraced his steps to the alley where he had left Dean. They had fifteen minutes.

When Castiel returned, an insurmountable amount of panic overtook him.

He wasn't there.

Dean. Was. Not. There.

His first thought was that this was the wrong alley-way. That small comfort was quickly ripped away from him, however, when he spotted the cart he used to wheel Winchester out of the prison. He spun around wildly for any sign of the Rebel, almost ready to leave the alley when he heard a small grunt. He snapped his head toward the source of the noise. Walking further down the alley, a foot came into view, followed by a leg. Dean soon became visible behind a different stack of barrels. Relief swept over Castiel, yet his heart still pounded in his chest, adrenaline pumping through his system from the panic attack moments before.

"Winchester," he hissed, attempting to regain control of his emotions, "I told you to stay in one spot. You have no idea how-"

He cut himself off as he beheld Dean in front of him. The man was panting, clutching his side. A thin layer of sweat covered his skin, and there was a line of blood spilling from his mouth. Castiel looked the Rebel up and down, then looked back from the spot he initially left Dean. There was a barrel knocked over and, upon further inspection, he could see blood on the ground. He looked back to Dean. He didn't walk over to this new spot; he stumbled. He was trying to get away himself. He didn't trust him. While it was understandable, it was rather unsettling. But that was the least of his issues.

There was one thing he didn't take into account. And it was sitting right in front of his face. He was a fool. He took everything into account but the simplest and perhaps most pertinent detail.

"Dean… Can you walk?"

"Yeah I can walk," he snapped with his raw throat, "I've been doing it my whole damn life."

Castiel inspected him for another moment. "Dean, now is not the time to be proud. The shipment we must smuggle you out in draws near. I must be outside this alley in order to stop the trailer, allowing you to slip in under the tarp that covers it. Now I will ask you again. Can you walk?"

Dean tilted his head that was resting against the stone wall up to give Castiel an inspective glance. He then leaned up off the wall and moved to stand, obviously struggling. He made it about three steps before he gave an involuntary hiss and clutched his side yet again, falling against the wall once more. He gave a small, sad glance at the long distance down the alley, and then turned his head away from Castiel. After a moment Dean shook his head, still refusing to look at him, admitting defeat.

"Damn," Castiel muttered under his breath.

He needed a new plan. Fast.