The house that Castiel had provided for Dean to live in was small, but it was the most amazing and glorious thing Dean had ever seen; even when he was winning and making money, he had still never lived in anything bigger than a one room studio. It came furnished with basic items such as kitchenware, a couch, and an honest-to-god bed to sleep in. He had opted out in joining in on dinner the night before, still feeling out-of-place and awkward, which resulted in a pissed off stomach. Dean had exactly $2.26 to his name and he was not about to spend it unless he had to - but that also meant he'd be forced to mingle with the crowd for meals sooner rather than later.

Rummaging through his duffel bag he found a pair of jeans and a polo without holes in it and slipped them on. It was a gorgeous day outside and he was excited to begin working with the horses, especially Lazarus. Bobby had already fed them, and was pulling out supplies ready to start working on stalls after he turned horses out. "Leave Lazarus in," Dean requested as he pulled up his jeans on his hips. The leather on his belt had worn so much it snapped one day and there had been no money to buy another one.

"You gonna finally start that filly, huh?" Bobby asked casually as he reached for Asia's halter.

"Well, I gotta find out what I'm working with," Dean nodded. "I'm assuming Gabriel will be around to ride her?"

"You say that like she's actually been worked before," Bobby scoffed. "Gabriel's gotten a saddle on her and hopped on a few times, but no one has actually ever run her before."

Dean rubbed at his stubble, a bit agitated at the news, but with a sigh he decided it wasn't worth getting upset over. "Ok, well, no time like the present to do it. Is Gabriel here, yet?"

Bobby shrugged, "Haven't seen him, but doesn't mean he ain't hiding somewhere. Charlie was in the tack room cleaning some grooming tools."

Dean nodded, "Yeah, ok. I can have her get Laz ready until Gabriel finally decides to show."

"Not to fear, the Trickster is here," Gabriel purred as he bound playfully up to Dean. Gabriel was well known amongst other jockeys as the Trickster or Loki because of the practical jokes he always loved to play in the locker rooms; Dean resisted the urge to roll his eyes at the way Gabriel wore the title like a badge of honor. "So, am I finally going to have something to ride?"

"I want to see Lazarus on the track," Dean nodded. "I've got to know what I'm working with here."

Gabriel hummed, "Well, she definitely won't go into a starting gate yet."

"That's fine," Dean waved the comment off, "She's still a baby, I'm not worried about that. I just want to see if she'll even run."

Gabriel ran a hand through his long hair and stretched his body out. "Whelp, here we go. Alrighty, boss man, let's do this thing."

Dean was extremely grateful that Meadowland Farms had their own bullring. It was nowhere near the size of actual racing tracks, but that was easily made up for by running a few extra laps. Having it on property also saved money and time in trailering to an offsite facility.

Once Charlie had groomed Lazarus Gabriel tacked her up and grabbed his helmet, handing off the lead back to Charlie. "Alright, we're ready to go. Best way to the track is that-a-way," he nodded his head off towards the north end of the barn.

"Lead the way," Dean motioned and shoved his hands in his pockets, fiddling with the stopwatch that rested there. He was nervous. Even though this wasn't a race, this was a preliminary to see if the filly could even run.

"Do you want me to keep her in hand?" Gabriel asked as they followed Charlie and Lazarus up the dirt path.

"No," Dean shook his head, "I've got to know what she can do. I'm not expecting any record breaking times, she'll need conditioning, but I gotta know I have something to work with here. I'm not going to spout lies to your brother about her, no matter how much potential Anna thought she might have."

"A slow horse isn't good for anyone," Gabriel agreed. "He'll appreciate the honesty, either way."

"Honesty in what regard?"

Gabriel peeked over his shoulder at his brother, "About your horse sucking."

Dean turned his body enough so that he could still walk but acknowledge his boss. As he has been the day previously, Castiel was well dressed but with tousled hair. It was as if the man simply couldn't be bothered with trying to tame his bedhead. Dean couldn't help but imagine his fingers through it. "Morning, Cas."

"Dean," Castiel nodded. "I look forward to seeing Lazarus run."

Dean gave a nervous huff, "I hope it's worth seeing. Alright, Charlie, you can go ahead and stop her here." Dean laced his fingers together and offered a boost to the jockey. Charlie had to keep a heavy hold on the filly once Gabriel sat on her back. Lazarus began prancing, ready to go. Dean motioned for the groom to hand him the lead and he took hold of the filly and walked her through the gate onto the track. "When I give her to you just let her get comfortable and warm up around the first lap. Once you hit that first pole, you give her all you got. I'm gonna clock her at the second quarter-mile pole, give her some time to get her at full speed."

When Gabriel gave a nod of his understanding, Dean unhooked the clip and let the filly go. Pulling out his stopwatch he made his way back out to the outside of the fence next to Charlie and Castiel. "Well, she's got a lot of energy I'll give her that."

"She looks great," Charlie beamed.

"Are you not worried how wound up she is?" Castiel asked with a furrowed brow.

"Nah, she's just fresh. It's not nervous energy," Dean explained. "Alright, here we go." Gabriel had Lazarus in a canter and was riling her up into a gallop as they approached the first pole. The three watched in silent unison as Lazarus lengthened to full stride. As she approached the second marker Dean started his stop watch. Everyone held their breaths as Lazarus snorted her way along the track, and then there was the click of the watch once more. All three sets of eyes moved to the watch. Dean's mouth dropped and his body froze.

"Your watch is broken," Charlie murmured, her face in equal amounts of shock.

"I don't understand," Castiel frowned, "is that a good time?"

"How'd she do?!" Gabriel called from the other end of the track, trotting a snorting Lazarus back towards their direction.

"That can't be right," Charlie took a step back, "That's faster than War Emblem and Funny Cide's quarter-mile at the Derby!"

Dean gave a slow blink and shook the stopwatch thinking the time might change, but it didn't; The hand was irrefutably still stopped at 24.2 seconds. "Son of a bitch."

"That's good, correct?" Castiel asked, impatiently looking between the two of them looking for some sort of explanation.

"Don't leave me hanging!" Gabriel groaned as he brought Lazarus back down to a walk despite the filly's protest. "She felt pretty fast."

"24.2," Dean answered plainly.

"WHOA!" Gabriel was instantly off Lazarus and grabbing for the stopwatch in Dean's hand.

Charlie hopped the railing and took hold of Lazarus before she could run off. "She was amazing!" The groom gave the filly a loving pat and rub.

"So this is good?!" Castiel asked again.

Dean shook his head violently, "Yeah. Yeah! I mean, there's a million factors that could still come into play - like track conditions, how she reacts to dirt in her face, traffic - but," He put his hands on his head and rubbed one down his face. "This is awesome." Dean could not even begin to explain how awesome this really was. A fire was suddenly ignited within him, and he felt so alive. "Charlie, go ahead and cool her down real well before turning her out. I'm going to get a training regiment going on her immediately. We'll need to pull out those gates over there, too, and start training her on that.

Charlie gave an excited nod and began walking Lazarus back, a bounce in her step as she snaked an arm underneath the filly's neck and began patting her over and over with praise.

Gabriel unfastened his helmet and placed his hands on his hips. "I'll be damned. Maybe Anna knew something we didn't. Bu-u-ut," he drew the word out purposely, "Dean is right."

"Hmm," Castiel hummed in thought. "So, if I understand correctly, she has the talent, but it is uncertain how she'll perform under stress."

"More or less," Dean confirmed. "We can simulate those conditions to a point. A lot of trainers never do. They throw them out on the track for their first race and that's the first time they've had dirt fly in their face or have another horse bump into them-"

"Which is illegal, mind you!" Gabriel interjected.

Dean gave a roll of his eyes, "Anyway. It might be beneficial to think about hiring on another jockey if we do pick up some colts so that we can prepare them for an environment similar to race day."

"Uh, I'll pass, thanks!" Gabriel protested.

"I'm not throwing you to the curb," Dean began, "But if we do get more colts and they all turn out to be successful, it's not like you can ride all the horses in the same race."

"Watch me! It'll be the best damn trick I've ever done!"

"Gabriel, honestly," Castiel sighed in annoyance. 'If Dean feels that is best-,"

"Oh, so now it's what Dean feels is best." The pissed-off expression was what both Castiel and Dean expected, but instead they received a devilish grin and wiggling eyebrows. "What do you find feels best, Dean? My dear bro isn't really that experienced, and it's better if you just tell him what it is you like and -,"

"Gabriel!" Castiel's face was completely red in embarrassment. "Please, that is enough."

Gabriel threw his hands up in the air in defeat, "Ok, ok. I'm just trying to be a good brother here and help you out, but I see where I'm not wanted."

Nervously sliding his glasses back up onto his nose Castiel turned back to Dean who had the most amused grin on his face from the situation which only heightened his nerves. "Dean, I was really hoping you could join me for lunch-"

"Oh-ho!" Gabriel had begun walking away but fast-tracked it right back in between the owner and trainer. "Look at you, Cassie! I'm so proud of you asking Dean-o out on a date so quickly!"

Castiel's body shrunk in on itself, "No, I-I didn't-,"

"You dog, you," Gabriel purred in approval.

Dean couldn't help but laugh, blissfully reminded of the days spent with Sam bickering over mindless things. Even if Castiel wasn't asking him out on a date, there was a big quiver of his heart at the invitation. "It's ok, Cas, I knew what you meant. I'd be happy to have lunch with you to discuss business." He might as well step in and help save the poor guy from his brother.

"Business! Yes," Castiel nodded fiercely. "Strictly to discuss business."

"Getting down to business is more like it," Gabriel cooed as he finally decided to walk away from the two.

"I am so sorry," Castiel spoke, still blushing like a complete virgin. "That was extremely inappropriate of him."

"Don't sweat it," Dean smiled, placing an encouraging and lingering hand on the man's shoulder, "I have a brother, too, you know." With a gentle squeeze he let his hand fall and shoved it in his pocket. He hoped that Castiel understood what it meant. They continued to walk down to the barn in silence, and Dean feared that either Castiel didn't understand, or he did not want to act on it, but then he finally decided to speak.

"I had initially intended that you simply join us for lunch at the main house, but with Gabriel being on a roll with his antics, I think I'd prefer it if we went somewhere instead."

Dean let out the breath he had been holding. Perfect. Dean didn't feel comfortable asking his boss out, but if it were the other way around...Granted, he could hear Sammy in his head yelling at him for being attracted to his boss in the first place, but it wasn't like this was some corporate work place. "Sure, whatever you want, Cas."

"Um," Castiel stopped in front of the barn. "I don't exactly...Well. I don't drive. I mean I can, I just-,"

"Well, it's your lucky day because I have a car and can drive." And he hoped to fucking God that baby still had enough gas to get them there and back. "What time did you want to go?"

"It's still early yet. Perhaps right at noon?" Castiel suggested.

"Sure. That can give me some time to have Gabriel work some of your other horses."

"I'll leave you to it, then," Castiel gave a soft smile before turning on his heel and heading back to the main house.

Noon took a lot longer than Dean would have liked to come along, but Castiel was waiting and ready for him at his house by the Impala right on the dot. "Beautiful car," he commented. "Impala. What's the year? '67, '68?"

"Oh, so you know a little something about cars?" Dean asked, impressed, as he opened up the driver's side door. "'67," he answered as he hopped in. Both passengers shut their doors and he lit up the ignition. "How did you get to know that?"

"I'm a historian. Was," he sighed, clearly showing some disappointment that it was no longer the case.

"So that's what you did before you came here?" Dean made his way down the driveway and Castiel pointed to the right.

"Yes. I worked for the Smithsonian."

Dean's eyes lit up, impressed with the fact, "Geez. My brother would have a field day. He's a huge nerd. The two of you could go at it all day long."

"What is it your brother does?" Castiel inquired.

"He's a hotshot lawyer out in California. Went to Stanford. Got himself a wife," Dean knew he had a goofy look on his face, but he couldn't help it when it came to talking about his brother. The kid was definitely his pride and joy.

"You sound very proud."

"I am," he boasted confidently. Looking down at his gas gauge he bit the inside of his lip. This place better not be too far out there. Thankfully, it wasn't, as Castiel instructed him to pull in to a small but nice cafe.

"I've never eaten here," Castiel admitted as they made their way out of the Impala, "but Missouri suggested this side of town for places to go. I hope this is alright."

"It's fine," Dean assured. It was more than fine. It was something other than gas station garbage bin leftovers. He just really hoped Castiel had intentions of paying...Dean really wished he could avoid any talk about how he had been homeless prior to being hired on.

They got a table for two by a window and ordered their drinks and food. Even though it was a small and rather inexpensive cafe, Dean still felt out of place. Everyone looked a lot like Castiel; nicely dressed and sophisticated. There was definitely nothing but money in the area.

Castiel took a sip of his coffee and struck up conversation. "So after your first day with the horses, what are your overall thoughts?"

"Well," Dean wiped his hands on his napkin, "We already know I think Lazarus has a lot of potential. I think all the other horses you have got about a year left of some Grade III and maybe Grade II races. They are in really good shape for how many starts they've all had. Anna took good care of all of them, but I still think it's a good idea to get a few colts in case Lazarus gets hurt or just doesn't perform."

"No, I agree," Castiel nodded. "You said you had some in mind?"

"There's two that I really like, and I think if you don't mind paying for them, we should get them both. There's French Mistake who has a lot of great sprinters in his bloodline, and then Mystery Spot who has a lot of distance, but also some sprinters. You have a great chance at winning one of the Triple Crown races with those two." Dean had seen both of the colts in person before, and he had been dying for the longest time to be able to train them, but it wasn't until now that the possibility seemed real.

"If those are the two you want, I have no reason to disagree. I would like to have you present during the dealings. You know more how it is done, and what they are worth me paying." Castiel took another sip of his coffee and thanked the waitress when she took his plates and asked if he wanted a refill.

"Yeah, that's no problem. I can get you all the contact information when we get back," Dean smiled, excited to see the deals go through.

Castiel cleared his throat and fiddled with the rim of his cup, "I know I said this was a business discussion, but I was rather hoping we could get to know each other a bit further if we are to be partners in this business."

Dean swallowed, uncomfortable with the thought of what his employer could potentially ask, but he nodded anyway. "Sure. Ask away."

"This goes both ways," Castiel said. "If you have a question, I hope you ask it. May I inquire as to what got you into racing?"

"My dad," Dean answered simply, not feeling a desire to explain it any further. Unfortunately, Castiel wasn't going to leave it at that.

"Yes, I...didn't mean to overhear, but when you and Bobby reunited in my barn he mentioned something about your father. May I ask what happened?"

"No," Dean replied without hesitation. Dean promptly noticed Castiel flinch at the response and instantly felt regret. "I'm sorry, I didn't mean-,"

"Nonsense," Castiel interrupted, "you clearly don't feel comfortable with the subject and I should not press the issue."

"It's not...that," Dean ran a hand across his temple and sighed. "Look, it's not like you couldn't find out if you really wanted to know. It's practically plastered all over the internet. I don't know how much you knew about me before hiring me on, but I'm considered really bad luck in the racing world."

"Yes, Bobby and Gabriel did mention you've had some bad horses of late," Castiel nodded.

"It's not just that," Dean groaned. He leaned back against the chair and stared up at the ceiling, contemplating the best way to go about explaining. "My dad was a trainer, too. One of the best of his day. His horse, Michael's Sword, was horse of the year. Everyone was saying he was going to win the Kentucky Derby and probably the Triple Crown. My dad decided to race him in a stakes race two weeks before the Derby - which was fucking stupid - and the horse had a bad break and got caught up between two other horses. The horse broke its leg and the jockey went down getting trampled underneath the field. Michael had to be euthanized on the track. The jockey was already dead by the time the ambulance got to him." Dean couldn't bear to look at Castiel. Instead he focused on the cup that was in between the man's hands. "Everyone blamed him for the horse and the jockey's death. No one would hire him and he began drinking really heavily. He got so drunk he turned violent and," Dean sucked in a shuddered breath and licked his lips, "He got violent with my mom, and she killed herself."

Castiel let a gasp escape his lips. "Dean, I'm so-,"

"Save it," Dean sighed. "For some crazy reason my mom put up with it, still believing he could get past it, but my dad doesn't give two shits about moving on. If he really wanted to get better he'd get off his ass and check in to a rehab center. Bobby blames himself. He and my dad had always been best friends. He feels like he didn't do enough to stop it. I don't blame him, but he still cut himself off from me." Dean remembered night's worth of trying to get a hold of Bobby on the phone and never hearing a response. It had killed him thinking he'd never speak to him again. "I really am sorry about Anna."

"Hmm," Castiel drew out a sigh. "I'm just sorry I did not take more opportunities to meet with her. I was always so involved with my work that I blew off every opportunity to just be with my family, and now she's gone forever. My father ignored all of us when I was younger, and I did not appreciate it. It turns out I turned out just like him; focused far more on my work than my family."

"Is that why you decided to leave your job to take over the farm? You thought maybe it was a second chance?" Dean asked curiously.

"Not a second chance, but rather...a way to redeem myself. I suppose, if redemption is even possible," Castiel let his gaze fall as he took the final sip of his coffee. "I loved my job. I already miss it dearly, but I realized that they could easily find someone just as qualified as me to fill my shoes if I were to leave. If I decided to abandon the farm, I would completely destroy people's lives; Bobby, Charlie, Gabriel, Missouri...you."

Dean's eyes locked with Castiel's. He could feel his heart beating in his throat. "Cas...you didn't have to feel obligated-,"

"I did not decide to stay until after I had already hired you on," Castiel admitted. "I realized that if I left and sold the farm, youmost likely would not be held on as trainer. I just...I couldn't do it."

"Cas," Dean felt himself choking up. He had never had a boss care anything about his own well being. "I...you've changed my life. You've changed everything. As selfish as it sounds I'm glad you decided to stay."

Castiel let his lips curl into a smile. "I could say the same for you. I called countless of trainers, and not one for them would even meet with meet face-to-face. If it weren't for you, I would have given up and gone home regardless. You took a chance on someone who knew nothing about horses."

"And you took a chance on a loser who can't win a horse race," Dean chuckled. "I guess we are even."

"Indeed," Castiel agreed. Taking in a deep breath Castiel grabbed the check and pulled out his credit card. "I believe we have some horses to buy, then?"

Dean nodded, a heavy weight suddenly lifted off his shoulders. "Let's do it."