A/N: I promised you all that even though I wasn't going to be in the DCBB I'd still post the story! Unfortunately, if you read this story via you miss out on the great art! Please head over to Ao3 or my Tumblr to see the artwork I've done for each chapter. The story is complete, but I have to do art for each chapter, so postings will be staggered. Enjoy the ride (pun intended)!

Castiel removed his glasses and rubbed at his weary eyes with the back of his hand. Blinking through the blurriness he glanced at the clock across the room and sighed at the time the bright green letters yelled back at him. Translating this piece of text had become such an important task for him that the man barely slept at all these days. At this point however, he was becoming quite useless in the task.

Leaving his glasses on the desk he made for his bedroom, clothes falling to the floor in a trail behind him. The bed sank underneath his weight as he finally allowed his fatigued body to fall. Just as he was shoving his feet under the covers his cell phone, still on the bedside table from when he plugged it in yesterday, rang. Castiel let an exasperated sigh fall from his lips as he reached over to tilt the screen enough for the caller ID to show.

Gabriel.

Frowning, Castiel sat up in the bed and accepted the call, suddenly feeling wide awake as concern filled him. He and his brother rarely spoke, both too busy with their respective lives to do much more than pass messages on through Anna. Gabriel wouldn't call him himself, not unless something had happened. "Gabriel? What's wrong?"

Gabriel's voice was shaky as it came through the receiver. "Castiel… It's Anna."

Castiel felt his skin grow cold. His room was already quiet with its bare walls and lackluster colors, but it went completely as he forced himself to ask: "What is it? What's wrong with Anna?"

"Bro…. She's dead."

Castiel's breathing stopped as he brought his free hand to his mouth, trying to digest that simple sentence. There was a moment of denial and then question after question shot through his brain. "What...What happened?"

"Drunk driver… Hit her dead on. They say she died instantly. Cassie, I need you to come down here. I don't know what to do. The farm… the horses. What's going to happen to it all?"

Castiel wiped the tears from his eyes and took in a deep breath, pushing aside his grief for now to focus on Gabriel. "I'll get the first flight out to Lexington that I can. Can you pick me up?"

"Yeah, of course. Just let me know your flight information when you get it."

Thankfully, it didn't take long to get a flight from D.C to Lexington. It only took a single call to his boss at the Smithsonian to get two weeks leave approved to handle funeral arrangements and the farm, but she had not been pleased about it despite the circumstances. The only part of the flight Castiel even remembered was take-off and landing. It was much needed sleep, especially since he feared it would only get worse as the lawyers started coming in.

Once he'd gathered up his bag from the conveyor, he stepped outside the terminal and there was Gabriel, waiting for him as promised. His older brother looked even worse for wear than the reflection Castiel saw that morning in the mirror, the age lines usually overlooked in the face of Gabriel's never ending energy standing out prominently on his face. For half a moment Castiel felt the distance between them as a living thing, overwhelmingly great and hopelessly insurmountable. Then Gabriel caught sight of him and smiled, his relief clear, and the moment passed. Castiel stepped forward into his brother's tight hug. "Gabriel… It's good to see you."

"Yeah, you too, bro. Just wish it weren't like this," Gabriel responded as he helped his brother get his bag into the trunk of his car.

Sadness tinged both their expressions at that. "Me too."

The silence after that felt very awkward to Castiel, though a glance suggested Gabriel was not bothered by it, perhaps taking it in stride as they rounded the car to settle in. Still, he struggled to think of something to fill the void. "I saw where you won the Breeder's Cup on Asia," he eventually settled for, thinking Gabriel's career would be safe ground as he settled into the passenger's seat.

Gabriel gave an amused snort despite the still lingering sadness. "That was two years ago, bro."

Castiel's cheeks flushed red. "Oh…"

"It was a good race though. Nothing like singing 'Heat of the Moment' to your competitors as you blaze right past them."

"I apologize. Time seems to just… fly by these days."

Gabriel started the engine and began easing out of his parking spot. "I don't know how you keep time straight period, being a badass historian and all. Is that still going okay for you?"

Castiel gave a halfhearted smile at the familiar joke. Honestly, historian was an oversimplification of his career, but he no longer took offense at it as he once had, having recognized eventually that Gabriel's insistence on ignoring his corrections was teasing, not insult. That it had taken many long conversations with Anna to reach that point was irrelevant. His brother tried and that was what Castiel took to heart. "Yes. I enjoy it very much, despite its long hours. How has riding been? And the farm?"

"It's good, been good… It's been real good. We've…" Gabriel had to pause to keep himself from choking up. "We've had good horses and good wins, bro. The past year we haven't reallyhad anything because Asia had just given birth, but her filly is ready to start. I mean… We were really hoping for a colt. It was always Anna's dream to get to the Derby – and shit, mine too – but Laz isn't going to get us there. All our other horses are racing great, but they're all over three and need to be put to stud soon."

Castiel's eyes narrowed in confusion. "I don't understand. Are fillies prohibited from running in the Derby?"

Gabriel gave him an exasperated glance and the corners of his mouth tugged up. "How are we even related? No, but they aren't as fast as the colts. I mean, there's been a few to race in the Derby – maybe thirty-five, but of those only three won. The odds just aren't good. I'd finally convinced Anna we needed to start looking for some young colts to break, and then…" He swallowed hard and stared straight ahead, his golden eyes focusing on the road too intently to really be seeing it. "I don't know what we're going to do, Cassie."

"Why don't you take over the farm?" Castiel suggested quietly. "You know the business better than anyone."

Gabriel was shaking his head before the words had even finished leaving his mouth. "Hell no, bro! I can't be a jockey and try and run the business, too. It just doesn't work that way." He shifted in his seat and, with one last glance at Castiel, turned the radio dial up so that the rest of the drive involved no further conversation. For Anna's memory, Castiel chose the side of tact and pretended neither of them knew he wasn't suggesting that Gabriel do both.

Meadowland Stables was nothing like Castiel remembered and everything all at once. There were a hundred acres of beautiful green grass and the stables were located on the east side of the house like he recalled, but everything looked newer and more expensive. Anna really had done well for herself. Castiel spoke with her over the phone often, but neither of their schedules allowed for them to see each other much and when they did it was always her coming to him when a race brought her that way. He hadn't been back to the farm in what he was only now realizing was years.

Gabriel drove up the driveway, its path lined by a beautiful white fence nicer than Castiel remembered and thick oak trees. The large iron gate was already open and inviting as they drove through and towards the main house. Gabriel pulled in towards the garage and muttered out a curse as he noticed the black suburban already parked there.

"What's wrong?" Castiel asked.

"That's Anna's lawyer, Victor Henriksen. He's a good guy, I just… Shit, this makes it all real, you know?"

Castiel nodded in understanding and put a comforting hand on his brother's shoulder. "Come on, let's get this over with."

Victor had been waiting in his car and opened his door in unison with the two brothers. "Gabriel. And you must be Castiel… My condolences." He held out his hand and shookeach of theirs in greeting. "I know you are both grieving, but we really need to go over Anna's Will and get all her finances sorted out."

Castiel nodded. "Of course. Follow me."

Shortly enough they were settled in the drawing room, Victor's leather briefcase open on the mahogany coffee table as he pulled out a considerable stack of papers, and without even time to set his luggage in his room, Castiel found himself waist-deep in this new world without his sister in it. Gabriel was by his side initially, but soon the legalese - or the reality of their loss - had the man fleeing out of proclaimed boredom, instructing his brother to come fetch him when his name was mentioned anywhere. Victor had paused at that, casting concerned looks at Castiel's rumpled appearance and suggested they all break for lunch, but Castiel shook his head and motioned for him to continue.

They made good time, but there seemed to be no end to the papers to sign or accounts to be reviewed, and by the time he and Victor made it to the heart of things Castiel was well and truly exhausted.. But there it was, the end of things, the final pages in his sister's life. Anna left the horses and personal effects to Gabriel and most of the finances to the farm itself. She wished, quite clearly, to be cremated and buried with her previous horses in the back acre. And of course...

"That leaves the farm itself." Victor flipped to the next page of the Will and began to read: "I devise, bequeath, and give all of the remainder of my estate and Meadowland Stables as follows: 100% to Castiel Novak."

Castiel's pen dropped to the table with an abrupt clatter. "What?"

"Castiel, she's leaving the farm to you," Victor reiterated.

Castiel pushed his glasses up on his nose and shook his head. "That's not possible. I know nothing about this business."

"Well, it's about time you learn - or sell the farm."

Castiel rubbed his temple and swiped a hand over his face before pushing his chair back and standing. "I need a moment, if you please…"

"Of course." Victor nodded, beginning to fill out some paperwork as Castiel left the room.

He headed for the kitchen, not sure what he intended to do, but thinking distantly of splashing water on his face. He found Gabriel there, sucking down a beer pensively.

As soon as Gabriel noticed Castiel's entrance, he gave him a curious look. "Geez, Anna come back to haunt you already?"

Castiel didn't respond at first, his head down, before he finally realized his brother had been speaking to him. "What?"

"Jesus Christ, kiddo, you look like you've seen a ghost. What did Henriksen have to say?" Gabriel popped the top to a second beer and offered it to his brother.

With shaking hands Castiel took hold of the beer, and downed the entire thing before wiping at his mouth with the back of his hand. "She left the farm to me."

His older brother's eyebrows shot up. "You're joking. I mean, I kind of wondered when it wasn't left to me, but you?"

"Gabriel, I… I can't, I-" Castiel grabbed at his chest, the fog that had settled into his head while he went over Anna's will suddenly creeping further into his awareness as it seemed to get harder to breathe in air.

"Whoa!" Gabriel jumped up, dropping the beer on the table in favor of grabbing onto his brother's arms and guiding him to sit in a chair in the living room. He practically shoved Castiel's head between his legs. "Breathe, baby bro. Inhale, now exhale. There..." He knelt down so that he was looking up at Castiel's downcast face. "Anna left the entire farm to you?"

Castiel nodded, still feeling panicked. "Gabriel, I barely know anything about horses. How could she possibly do this?"

"Hey, calm down." He put a comforting hand on his brother's. "You deal with most of the business stuff at the Smithsonian, right? All the costs as far as managing and getting ancient books and stuff you need, right?" There was a nod. "And a lot of being a historian is record keeping?"

"Well, technically-"

"Yes or no, bro?"

Hesitantly Castiel nodded.

"Well, see, you're halfway there."

"But I know nothing of what horses are the best to buy or bloodlines to breed to!" Castiel protested.

"Research, buddy. That's all that is, and I'm pretty sure that's something you are good at, considering. I'll be here to help you every step of the way, I promise." He took both of Castiel's hands in his. "Please, bro. I need you to try. You can't sell the farm."

Castiel sucked in a shuddered breath, nodding slowly. "I couldn't do that. Not to Anna... This was everything to her."

"Good," Gabriel smiled as he stood up. "The first thing you need to know is that as a business owner you're going to have to deal with bad news a lot. In fact, I have some for you now. When our previous trainer found out Anna has passed, he didn't want to stick around to see what would happen. We officially have no trainer for our horses."

"So then we need to hire another one," Castiel inferred.

"Yup."

"I don't suppose you have anyone in mind?"

Gabriel snorted. "Who's going to want to take on a filly as the main prospect of the farm? Yeah, right. We need to buy colts to attract trainers, but we need trainers to buy the colts."

With a heavy sigh and an even heavier heart, Castiel shoved his face into his hands. How was he ever supposed to manage all of this?

/*/

"Come on, baby, come on. Push him to the outside, there you go."

Dean Winchester gripped tightly at the railing in front of his seat, bet stub firmly in his hand. He was wearing a worn sport coat with patches where the fabric had withered away to bare threads. His slacks were faded and the soles of his boots were so thin he swore he could feel the gravel on his skin as he walked. The green striped tie was about the only thing on him that did not look like it had seen a war. He couldn't even manage an actual dress shirt, instead wearing a lighter green polo underneath the coat.

The horses rounded the final turn. "Come on, Khan; come on, baby. Come on, Don, let him go! The hole is right there!" Dean gripped at his bangs as he watched his horse slip further and further to the rear across the finish line. "Son of a bitch!" He threw down the stub in anger and made his way out of the stands back towards the stables. His boss was just ahead, storming towards him which was great because that was just who Dean wanted to see. "Rufus, Don needs to go!"

Rufus crossed his arms as he came to a stop in front of him, his dark face as forgiving as stone as he stared hard at the trainer. "Yeah? Well I'm sorry, Dean, but it's not Don that needs to go."

Dean's green eyes widened and he jerked back, feeling a horrible sense of foreboding. It was a force of will that had his spine straightening and his mouth going seconds later, ready to defend himself. "What?! Rufus, come on! Don didn't let go! Khan had plenty of stamina left if the fucking idiot had just let go!"

Rufus shook his head. "I'm sorry, kid, but you are just bad for business these days. You had your run and it's over."

Dean grabbed the taller man's arm as he turned to walk away. "Rufus, I need this job! I don't have anything left."

"You should have thought of that before you went and blew everything you had. Boy, you were one of the best. You had everything. It ain't my fault you didn't know how to handle your money better." Rufus shook Dean off his arm and continued on.

Dean stood there unmoving, feeling himself going into a state of shock. "Rufus, please," he begged.

"Sorry, Dean," Rufus responded without turning back, the man having no intentions of carrying on the conversation any further.

Dean turned his back and tilted his head to the sky to try and blink the tears back. With a hand rub down his face and a pinch of his nose he began a slow amble to the only thing left he had to call home. The Impala was sitting there as it always was, black paint spotless and chrome shining bright. Dean drove to a small liquor store a few blocks away from the track and pulled out the last wad of cash he had to pay for a bottle of Jack.

When the trucks and trailers cleared from the race track he parked back behind the barns and moved to the back seat where blankets were sprawled out on the floor. Shucking himself out of the jacket he bundled it up and stuffed it underneath his pillow. With a deep sigh he crossed his arms and let his body settle on its side into what was likely to be a permanent bed for the foreseeable future.

Just as Dean finally felt his eyelids begin to close his phone began vibrating violently underneath his head. It took some groping to find the pocket and get the phone out, but eventually he had it in hand, the name "Bitch" sprawled in white across the screen. "Hey, Sammy," Dean answered as he settled back down.

"Dean! You never called to tell me how the race went!"

Dean swallowed. "It uh, it went good. Didn't win, but in the money." He hated lying to his brother. There was always the feeling of guilt in the pit of his stomach, but Sam had enough to worry about between his law-firm and wife.

"That's good! When are you finally going to come visit?"

Dean rubbed at his eyes, suddenly uncomfortable. He'd had this conversation enough to recognize the direction it was heading in. "I don't know, Sam. You know I'm busy."

There was an annoyed sigh at the other end. "Dean, is it the money?"

And there it was. "No," he insisted, too defensive by far. Wincing, he tried to cover. "I just don't have the time. Maybe in a few months, alright?"

"Dean, you know I'd help you out if you needed it, right? All you have to do is ask."

"Stop worrying yourself, Samantha, I'm fine," Dean reiterated.

"Okay… Well, just, call more often, alright? I worry about you."

"Yeah, yeah, this is about to become a serious chick-flick moment. Tell Jess hi for me, okay?"

"Sure thing. Bye, Dean."

Dean hung up the phone and tossed it into the front seat. He knew his brother would spot him any money he needed without hesitation, but to be honest he had far too much pride to ask for even a penny. No, Dean got himself into this mess so he was going to somehow see himself out. But the road in front of him seemed to go on without an end in sight… For the first time since his mother had died, Dean cried himself to sleep.

/*/

For the twenty-fifth time that day, Castiel found himself hanging up the phone in disappointment, now with only five days left before he had to be back in D.C.

Gabriel had introduced Castiel to the staff and the horses the day after the funeral. Bobby was the stable help, a gruff old man who always had something to say. Charlie was the groom, a cheerful young woman who had bonded well with Gabriel between their crude jokes and references to things Castiel did not understand. Then there was Lazarus, the young filly Anna had seen so much promise in. She was young and had a bright spirit, always running around in the pasture with the other horses.

Castiel had researched Lazarus's blood lines and gathered all the information he needed to sell the filly to potential trainers, but they all laughed in his face at a filly being the farm prospect. Removing his glasses he placed his face in his hands and let his shoulders fall. Gabriel had given him hope at first, but now it all seemed like an impossible task.

There was a soft knock at the door and Castiel looked up through blurry vision. Reaching for his glasses his sight cleared to find Bobby at the doorway. "Ah, Mr. Singer. What can I do for you?"

"Not to snoop into business that ain't mine, but I got a call from an old buddy of mine a few days ago. Said he had a guilty conscious about firing his trainer and wanted to know if I knew anyone who could help the kid out," Bobby explained.

Castiel's lips tightened in a thin line. "Why not simply hire the man back if he feels so guilty? Why was he fired in the first place?"

"It ain't his skill or character if that's what you're thinking. He used to be one of the most successful up-and-coming trainers in the business, but he started to hit a spell of bad luck. People in this industry are a tad suspicious about those kinds of things. As soon as word got around, no one wanted to touch him with a 10-foot pole."

"But you are suggesting I do as such?" Castiel frowned.

Bobby shrugged. "Doesn't sound to me like you're having much luck on finding anyone else."

With a contemplative sigh Castiel rubbed at the side of his temple before pushing his glasses back up the brim of his nose and making eye contact. In all honesty, he needed a trainer so badly, it wasn't much of a decision. "What's his name?"

"Dean. Dean Winchester."