Note: This little story has been stirring around in my brain so I figured I would get it into writing! I like the idea of older brother Harvey so this is my take on it. This story is slightly canon divergent, it exists in a time where Pearson Specter Litt is fully in tact and Mike (and Rachel) and Jessica have yet to leave the show. It won't really follow a lot of the regular show legal drama plot but we'll see.

I have tried to follow the Specter family backstory as best as possible, I'm not sure it exactly lines up with the canon plot. In The Painting, Lily mentions Harvey has been mad at her for 20 years. In this story, Lily was pregnant with her and Bobby's daughter when she finally split from Gordon, but I'm making that have happened 23ish years ago instead. Loose timeline change. Mainly trying to follow the basis of Harvey;s backstory otherwise. So, Harvey was 19 when she was born and Marcus was 16 or so.

Anyway, no need to explain anything else because this is a fanfiction! Enjoy! If you aren't into original characters, this likely isn't the story for you.

Harvey Specter was not the type to drink a fancy coffee. Yes, he had a French press and preferred a Brazilian roast. But most mornings a plain black coffee from the cart outside was sufficient.

The only time he granted himself a specialty coffee was Fridays. He and Donna had a long-standing tradition of Friday morning lattes from Stomping Grounds, a busy standalone cafe in the village. It was a bit of a distance from the office, but on Harvey's dime, Donna didn't mind.

"One large dirty chai latte with skim milk, one large iced coffee and one large hazelnut latte with whip for Donna!"

"Thank youuu!" Donna sang out her praise, reaching towards the counter to grab her tray of drinks. She balanced it on top of her white cardboard pastry box and smiled at the barista.

"Let me know how your boss likes those ginger snaps," the young girl commented as she continued to work, flashing Donna a smile.

"Well, he still won't shut up about your triple chocolate cookies so I'm sure these will be great." Donna returned the smile and waved goodbye to the girl, stepping outside into the warm September air. She saw Ray waiting for her up the street and headed into the car.

Donna made it to Pearson Specter Litt just after 8:30 and headed straight towards Harvey's office with the drinks.

"Thanks, Donna," Mike said as he grabbed his iced drink from the tray. She handed Harvey is hazelnut latte and left the box of baked goods on the table between the two as they sat on the couches.

"You should be thanking me, you know," Harvey joked with Mike, reaching down to grab a cookie.

"Harvey's money, my time," Donna gave Harvey a skeptical look.

Mike bit into one of the cookies and paused to smile, "I don't understand your loyalty to this coffee shop but I will admit the cookies are always delicious."

"You know, you could easily just not be invited to our Friday morning coffee tradition," Harvey replied to him, raising an eyebrow. "More cookies for me, then."

"You need to watch your figure, champ," Mike laughed at him, standing up. "I've got a date with some civil litigation case. Thanks again, Donna."

"Don't forget we've got that disposition at 11," Harvey called to him as he walked out.

"So," Harvey turned to Donna who was leaning against his desk, "Status report?"

Donna smiled and tilted her head at him, "She looks a bit more tired than usual, but otherwise her chipper demeanor remained. It was busy so we didn't really get to chat. I assume her classes are starting up again soon."

Harvey just nodded as he glanced down at the box of cookies, "This is my mom's recipe. Actually, my grandmother's." He smiled as he reached to grab another before standing up.

"You know, you could go do the coffee run next time," Donna suggested to him, her voice soft. "Check up on her yourself."

"It's not that easy, Donna," Harvey responded, letting out a breath. "You know our history."

"I'm not here to argue with you about it again," Donna continued, "But it's an olive branch. Sometimes the hardest thing and the right thing are the same, Harvey."

Emilie Bryant had a long, boring, terrible summer. She was looking forward to returning to her routine and busying herself with another year of school assignments. Studying Digital Art and Design was proving to be exactly what she wanted: a creative outlet paired with technological innovation.

Just past 1PM that Friday afternoon, she was pulling off her navy blue Stomping Grounds apron and falling onto a stool in the coffee shop and bakery's kitchen. She spent most of her time on the espresso machine, but early every Friday morning she whipped up a specialty cookie to sell at the front counter, too.

"Your ginger snaps were a hit, kid." Emilie smiled at the praise for her coworker Jackie. She was a full time baker and original founder of the bakery.

"Can't beat grandma's recipe," she replied, shrugging. She pulled her dark blonde hair out of it's tight ponytail and shook her head.

"So, excited for your last year of school?"

Emilie always appreciated the supportive chatter Jackie provided.

Living in the city could be a bit lonely, even if her mom and dad were just a phone call away. Em had worked hard to repair her relationship with her mother after being a terrible teenager, but the distance was difficult. Not having family around was hard, even though technically her older half brother lived and worked in Manhattan.

She was just 11 years old when she understood how she came to be. Her two half brothers, who were hardly a facet in her life growing up, were significantly older than her. It wasn't the first time hearing the word accident but it was the first time she understood it what it really meant. She later realized she was the product of her mother's affair. She cheated on her first husband, Gordon, with Emilie's father, Bobby. Her life was unintentional, a not-so-happy surprise. It tore up Lily's family and took a long time to fix.

And for Lily, having another child late in life was not the plan. Her father, Bobby, was happy to have a daughter and doted on her as she grew up.

They made it through. It wasn't easy. Emilie acted out in high school - drinking on the weekends, mouthing off to teachers, a long term battle with an eating disorder, ditching school. It didn't stop her from having good grades, but she knew she added a lot of stress to her parents' life.

She had a positive relationship with her brother Marcus. She babysat his kids when she used to live at home for the summers. But her relationship with her brother Harvey was an entirely different story. His animosity towards Bobby and their mother often left her defensive and hurt. Despite her previous desire to be kind towards him, they hadn't spoken in months. On the surface, it truly just felt like Harvey never liked her. So, she didn't care much for him either. Their issues stemmed from one accident and one fight when Emilie was a teenager. It never got back to normal. Of course Harvey did finally make amends with their mother, and that left Emilie and him to be civil, mostly.

After graduating, she did one year of community college in Boston before moving to Manhattan to go to NYU. Now, she was starting her senior year and looking forward to moving to the west coast after graduation.

"I guess I'm excited. I miss the routine! I'm also just grateful I still get Fridays off with my schedule this semester," Emilie finally responded to Jackie. She wasn't sure if she was being honest. She was just happy that summer was over. She grabbed her water bottle to take a sip, a yawn escaping her lips.

"Looks like it's time for your afternoon nap, Em!" She rolled her eyes as her coworker Ethan popped into the kitchen, grabbing a tray of fresh bread. Ethan worked full time at SG and Emilie had really taken a liking to him. She had only worked there for about six months now, and she was grateful to have a friend, albeit an annoying friend, in him. It helped they also had found a beneficial friendship outside of the coffee shop.

"On that note, I'm outta here. See you Sunday, Jackie." Emilie hopped off the stool and grabbed her backpack, smiling at her boss and waving to Ethan on her way out the back kitchen door.

She paused once she was in the back alley, plugging her headphones into her ears. As she walked away from the cafe, she could feel her spirits fade. She was looking forward to having the rest of the day free, but was dreading returning to her apartment. She still had to stop herself from heading toward her old place.

"You live in Queens now, dummy," she said quietly to herself. She sighed then continued on her way. She had a date with the gym, a welcome distraction from her worried thoughts.

She stared at herself in the mirror after running on the track at the NYU gym. A nice addition to the monstrosity that was her tuition. She was lucky to have help from her parents (and her brothers, though she never asked) to pay for college but she worked hard every summer to save for rent payments and normal spending.

Her eyes swept over her body frame in the mirror. She was tall enough and comfortably lean but she couldn't stop herself from criticism. She liked to run and had strong legs - but she still never felt like herself in her body. She ran her fingers through her shoulder length dark blonde hair and sighed. Her relationship with her body was an ongoing battle and today, she felt defeated.

As she left the gym, she called her friend Leah - they were volunteering at the orientation events at NYU the next morning and planned on ending their week with a wine night. Emilie was also hoping to sleepover with Ethan one night over the weekend, too.

She smiled to herself as she headed towards the subway. One more year in the city then life would go on. She may as well make the most of it.

Emilie knew it would be hard to ask for help. Especially from Harvey. But she didn't realize the first roadblock would be even getting into the Pearson Specter Litt office.

"I'm sorry, but if you don't have a badge, code or a registered appointment with a business in this building, you cannot access the elevators."

Emilie swallowed hard before letting out a breath. It seemed her first idea of asking politely wasn't working in her favour.

It was Thursday. She had hardly slept the night before and had been up early for a lecture. She wanted to skip it but she felt guilty missing classes in her first week of the semester. She had spent most of her class researching tenant rights in New York State again. She was left feeling pretty defeated but she didn't want to give up without a fight.

She smiled politely at the security guard in front of her. She took a quick scan of his name tag and tried again. "Look, Charles, I'm really in a bind here. Is there anything you can do to get me upstairs?"

He shook his head, then leaned forward at his desk, "Card, code, or appointment, sweetheart."

Emilie bit her tongue to save from swearing at the gruff man in front of her. She put her hands up to him as a sign of defeat and stepped back.

"Fuck," she let out quietly. She noticed a grey leather couch near the window. She wasn't even sure if her brother was in the building. It was late afternoon. She couldn't just wait. Or could she…

She plunked herself down on the couch and pulled a book out of her backpack. She gave the security guard a spiteful smile as he looked over at her. She knew this ploy wouldn't last long but she had nothing to lose.

"You can't just sit here all day," Charles said as he walked over to her. She knew he was right but she also knew all he could really do is ask her to leave then maybe consider calling the police about loitering. It seemed like a waste of resources but she had a feeling Charles' low intimidation factor didn't work out very well for him.

"If you had just let me go upstairs, I likely would have already come and gone. C'mon, Charles, I won't tell anyone you let me bypass the rules." She gave him a genuinely kind smile this time.

Charles didn't smile back

"Listen, Miss, you're going to have to leave," he said calmly, motioning to the door.

Before Emilie could continue protesting, a young dirty blonde 20-something stopped in front of them, a cup of coffee in one hand and a pretzel in the other.

"Chuck, didn't I say I owe you a pretzel?" he extended the salty snack to the security guard, flashing a smile. "What's going on?"

Charles took the offering and relaxed, "Just politely asking a loitering stranger to leave. But I think it's time for my 15. Promise me you won't be here when I get back." He nodded his head towards Emilie. She just shrugged at him. He rolled his eyes as he walked away.

The young man in the suit her a quizzical glance, "Are you reading The Hobbit in French?"

She nodded her head, her cheeks flushed as he looked at her. She tucked the book into her backpack.

"Huh." He smiled at her. "I would recommend you listen to old Chuck. He's not much for scare tactics but he has a friend in the NYPD branch a few blocks away. I've seen him excuse people for less than sitting. He runs a tight ship in this lobby."

She sighed, "Thanks." She paused as he smiled and began to walk towards the inside of the building. "Wait, do you work upstairs? Do you mind letting me through with you? I assure you I'm not a threat to this building."

"Sounds like something a threat might say," he laughed, then shrugged. "Sure." He motioned for her to follow him, as they headed to the elevators.

"What floor?"

She paused as the doors closed, glancing to the small directional sign. "Uhm, 41."

"Pearson Specter Litt?" He shot her another strange glance.

She nodded, turning to secure her backpack on her shoulders.

They rode up the elevator in silence, the suit quietly sipping his coffee with one hand and typing into his phone with the other.

When the elevator arrived at the 41st floor, he motioned for her to step out ahead of him as he followed.

She paused when she saw the front desk. The three receptionists were busy directing phone calls.

"Who are you looking for?" The suit asked her.

"Uhm, Harvey." She sighed and slowed down. "Harvey Specter."

"I'll show you his office. Is he expecting you?"

She laughed at his question, matching his calm pace as they weaved through the office. "Definitely not."

Emilie couldn't remember the last time she had seen Harvey in person. She had called him at the beginning of the year when she needed his help for something else, and he had not been responsive or helpful. In fact, their entire phone call had unravelled into a huge fight. Regrettable things had been said on each side. She had deleted all her contact info for him out of her phone. It wasn't their first fight by any means, but it was their worst one.

Despite her pride, she wasn't sure who else to turn to this time. She didn't have money for a proper lawyer and was really hoping he could set aside their differences and help her.

As they approached the end of the hall, Emilie took in the large glass walls, peering into each office as they passed by. They stopped in front of the generous corner office.

"Ten bucks says he comments on your jeans," the suit tilted his head to her, a smirk on his face. She glanced down at her legs. They were adorned with a pair of light denim, which had a few decorative holes. She let out a sigh. Her brother's comments about her clothes were the least of her concerns.

The young man in the suit tapped on the glass door and pulled it open, causing Harvey's attention to pull away from some documents on his desk. He glanced at Mike then to the girl beside him, with a confused look on his face. He stood up quickly, giving a double take to the pair at the door.

"Emilie," he took a few steps away from his desk. "Mike, you can go."

"I'd love to see how this plays out." Emilie glanced at the excited look on Mike's face, putting a name to the mysterious suit.

"You owe me case files for Berkow, so that should be occupying your time right now."

Mike shrugged and walked away, taking one last glance towards Harvey's office.

Emilie wasn't invited in so she remained on the outside of the door frame.

"Harvey, I need your help."

"Harvey, I pushed the partner meeting up to four, if you don't mind. Your calendar looked clear." Jessica paused as she remained outside his doorway. It was a warm Thursday for September, and she was hoping to enjoy a glass of wine on her terrace for once.

Harvey glanced up from the paperwork in front of him, noticing his boss at the door.

"Does Louis know we're not ordering in Malaysian then?" He smirked at her, shrugging. "Four is fine." He glanced at his watch. 3:40 already.

Jessica rolled her eyes and smiled, "Well, I'm hoping we can keep it under an hour tonight."

Harvey returned to his notes as she walked away, knowing full well that a partner meeting running less than an hour was a pipe dream. He sat back in his chair and glanced outside for a moment. It had been a long day. For whatever reason, he had been inspired to go for a run through the park in the morning, but his eager morning energy had certainly depleted.

The cool morning air was a refreshing reminder that fall was coming, which gave Harvey a strange sense of comfort. Fall was easy – crisp, warm. He shook his head from the distracting thoughts, returning to the notes from his recent disposition on his desk.

Moments later he heard a tapping on his glass door. He assumed it might be Donna – it wasn't uncommon for them both to hit a wall mid afternoon and need a break to chat. As he turned his head, he spotted Mike at the door with someone. Someone. His eyes widened for a moment when he realized he knew who that someone was.

That someone was his little sister Emilie.

He hadn't talked to Emilie in months. After making up with his mother a few years ago, he tried his best to continue an amicable relationship with his sister, especially since she was going to school in the city. But it hadn't panned out how he wanted. He made sure Donna checked in on her every week when she visited the coffeeshop she worked at, but seeing his sister in person after so long was a shock to his system.

Despite his tumultuous relationship with his mother, which he worked hard to repair, he had tried to be in his sister's life. He knew Marcus had more of a relationship with her. Most times he thought of her, which was more often than he would admit to most people, his mind immediately jumped to a younger version of her. Four-year-old Emmy building a card tower at the kitchen table in Marcus' old apartment. Twelve-year-old Emilie belting out a song at her school Holiday concert. Stick thin 16-year-old Em rolling her eyes with a cigarette in her hand. Those were fragmented memories of moments with his sister.

But standing at the door now was 24-year-old Emilie. No, 23-year-old Emilie. An adult version of his little sister. She had on short laced boots, eye roll worthy ripped denim, a plain black t-shirt and a heavily worn army green jacket. She had a backpack hanging from her shoulders. Her dirty blonde hair was pulled into a messy half ponytail thing. But it was her eyes that stood out most to Harvey – piercing blue, like his own. But they looked especially empty when he looked at her – empty and tired. He had seen her looking worse, much worse, at the peak of some troubling high school years. But seeing her in person here was comforting in a way. A reminder she was alive and well.

It was comforting until he remembered the last time they spoke.

He sighed and stood up. Emmy.

"Emilie." He took a few steps towards the door. What does she want now? It was unfair to assume his sister had some sort of alternative motive, but he knew this was not a social visit. Emilie and Harvey don't do social.

"Mike, you can go."

"I'd love to see how this plays out." Harvey did not have time for witty banter with his protégé.

"You owe me case files for Berkow, so that should be occupying your time right now."

He watched Mike walk away, knowing full well a strange interrogation was in his future.

Emilie remained at the door, hesitating to step into Harvey's office.

"Harvey, I need your help."

Harvey pursed his lips together and motioned for her to come in. He bit his tongue to avoid any unfair comments, a wave of memories of their last interactions coming to mind.

He returned to his desk chair and watched as she looked around his office for a moment.

"So, what's up kid?" She hated when he called her kid. "Do you really intentionally buy jeans with holes in them?"

Emilie dropped onto the couch and looked at her brother, ignoring his commentary, "I'm having an issue with my landlord."

"Again?"

"It's a long story. But I want to break my rental contract if possible without paying a penalty. I just don't know how to do that."

"Didn't we go over this before? You need to find a sublet or hope you have a forgiving landlord." Harvey sighed. He wasn't well versed in landlord and tenant law in the city anymore, he had bigger things to worry about.

"I'm trying but this is a bit more complicated than that, I think. I don't know. I just need some advice. If you would let me just explain everything." Emilie did her best to control her breathing and tone. Harvey's arrogance often came out when she asked him legal questions. She just needed an easy explanation.

"I don't have any time for this today, Emilie." He glanced down at his watch. "And I have a meeting right now."

"Harvey, come on, you know I wouldn't even be here unless I really needed -

"Free legal advice from your piece of shit lawyer brother? Wasn't that the term you used last time this happened?" He stood up from his chair, grabbing a stack of documents off his desk. Emilie sighed and rolled her eyes as she followed him out of the room.

"Harvey," she quickened her pace to meet his as he stopped outside of a board room. "Please, this is really hard for me to explain but I found-."

"My family and friends billing rate is $300 an hour." He said simply, cutting her off.

Emilie bit her tongue to stop herself from swearing at him. She wanted to fight back, and she knew he expected it, but she knew it wasn't worth it.

"Well, never mind. Thanks for nothing, Harvey." He raised his eyebrows at her calm response then went into the conference room, leaving her standing alone in the hallway.

Emilie didn't even bother giving him another glance. She just turned on her heel and headed back towards the elevator area.

She stopped when she saw Mike and a familiar looking redhead at the end of the hall. They were both leaning against another reception.

"Sorry to interrupt," she started, looking between Mike and the redhead. "Wait, do I know you?" She was a Friday morning regular at the cafe. "Dirty chai latte."

"I'm Donna, hi." Emilie smiled curtly at the introduction. "I've worked with your brother for years."

"Wait, what? Harvey's your brother?" Mike's jaw dropped open, looking from Donna to the younger girl.

"Half brother. Unfortunately." Emilie responded, a dry look on her face. "Would you have any recommendations for a legal clinic in the area?"

"Why? What do you need help with?"

"Mike," Donna said his name with warning. She looked over at him, doing her best to discourage him from getting involved.

"I need to get out of my rental agreement and Harvey charges $300 an hour, apparently." Emilie rolled her eyes and defensively crossed her arms. "Don't worry about it though, I'm going to just leave before he realizes I'm still here with his stupid Harvey spidey senses. It was nice to meet you both."

She smiled at them again then hurried away.

"Hey, wait up." She turned to see Mike catching up with her at the elevators.

"You know he's not going to act positively if you help me."

"I can handle Harvey. And I can spare 15 minutes, if you want some free legal advice."

"You had me at free."

"So, how come you don't talk about your secret sister?"

Harvey rolled his eyes as Mike quipped from across the room. Between the appearance and his argument with Emilie, plus a frustrating partner meeting, he didn't want to put up with Mike's shit, too.

"Emilie is not a secret."

"You've never mentioned her."

Harvey sighed, "What do you want to know, Mike?"

"Everything? She looks like you, now that I think about it. It's the smirk. Or the eyes."

Harvey wanted to shut him up. "Here's the summary: she's my half sister. My mom was pregnant when she left my dad. I didn't grow up with her, hell, I'm old enough to be her father, really. She goes to NYU studying something related to design and computers. She's turning 24. She works at a coffee shop. She's got an attitude problem and only talks to me when she's in trouble these days."

Mike watched him as he spoke. "Listen, Harvey, I'm not trying to insert myself into this part of your life, but I talked to her when she was leaving and-"

"Of course you did." Mike Ross and his do-gooder curse.

"I think there's more to this landlord situation than she told you. Or me. I don't know, she looked kind of scared."

Harvey looked over at Mike. Who was he to analyze his sister's emotions? Scared? Harvey would have noted if something was really wrong. He did catch that she didn't have much fight in her - usually she didn't give up so easily when someone said no, especially Harvey himself. Her eyes had looked tired. And empty. Maybe worried.

Harvey sighed. Maybe it was his turn to get the Friday morning coffee.