/this is purely a culmination of speculation and headcanons. It also strays from canon./
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Winter remembers the early days of her training. Her Father took it upon himself to teach her personally and in the beginning Winter was almost flattered to be scheduled into his busy schedule.
Her initial happiness was quickly extinguished when she found how cruel and demanding his training regime was. Hands that had never been worked became red and raw, palms splitting into angry bloody blisters. Her knuckles had been broken far too many times to fix, and as she grew older she hid her swollen, misshappen fingers beneath gloves.
He groomed her to be without flaw. Any mistake, no matter how miniscule, was punished. She would spend several hours training, alone in a room full of hired hunters and huntresses, as well as a few skilled fighters her Father paid handsomely to show little to no mercy when battling her.
Perfection was not a goal. It was a necessity. It was an ultimatum. Be perfect or face the consequences.
When she was of age she was enrolled at Signal. The rigorous training paid off, despite the permanent damages that it left her with. She was a favorite of many Professors, though it was nothing less than expected from the eldest Schnee.
When it came time to begin her term at Beacon, the subject of her future was once again broached. She was an heiress and there were certain expectations that would have to be met upon her graduation.
Winter would inherit the company from her Father when she was of age. She would run the company and she would be expected to marry soon after and continue on the line of Schnees.
It was an ever looming reminder that her life was not her own. She trained harder, pushed herself to the limits and made her name known to her classmates. Winter Schnee was a force to be reckoned with.
Her team was not memorable. They did not have the drive she did. They had nothing to prove, no limitations, no weighing expectations. They did not challenge her. She breezed through classes, hardly having to put in effort. She was forever restless with her coursework, always hungry for a chance to truly compete with someone on the level she worked at. It was halfway through her second year that she met someone just as motivated and hungry as she was. He was brilliant, however unassuming. If Winter was a force to be reckoned with, Qrow was a quiet storm.
Of course, he was horribly irritating. He moved effortlessly, put little thought into his fighting style. He moved smoothly, deliberately, clearly confident in his ability. It was exhilarating, to meet someone who was on the same plane as she was.
She made the mistake of adding feelings into their relationship, which had previously just comprised of battle training and mild teasing and bickering outside of class. It had happened so suddenly, so unexpectedly.
She had kissed him, to make matters worse. Winter had prided herself on being so controlled but he pushed her- and mid battle just as he had struck she caught his arm and pulled him to her.
He could have pulled away, could have ended it right there. Things would have been different if he had just rejected her.
He didnt, though. He didn't and it made everything so much more complicated.
In their third year he gave her a ring. It was incredibly presumptuous and he terrified her out of her wits when he presented it.
It was a promise ring, if sorts. A promise for the future. The thought of a future with Qrow was concerning. He was most definitely not a suitor her Father would approve of. He was reckless, had little to no respect for authority or her Father's company.
Still, she accepted the ring and wore it proudly.
She didn't tell Qrow that she hid it when she was around her Father.
It wasn't until the tail end of her third year at Beacon that the idea of taking another path other than the one her Father designed even occurred to her.
She met James Ironwood. He was stern, commanding respect and attention whenever he walked into the room.
Winter had the attention, was earning the respect, but she craved the uniform he sported.
He stood in as a guest speaker in classes for the week. She could feel him staring at her when she fought, felt his gaze boring down on her.
The need to be absolutely perfect was more pressing than she had ever remembered it being.
He approached her after class, finally, and she had been breathless when he offered her his hand. She had never met someone so worthy of her admiration. Ironwood offered her a position after she graduated.
"Your skill sets would not be properly utilized as a huntress."
Blood was pounding in her ears when he stepped away, leaving her with his card and a multitude of thoughts frantically racing in her head. She kept his card hidden and carried on with the remainder of her time at Beacon.
Her relationship with Qrow was strong and for just a slight minute she had allowed herself to truly believe that she could have everything. Having Qrow and a future as the Schnee matriarch were not two things that word coinside. Once her Father became aware of her relationship he threatened disownment. She clenched her fists behind her back and struck a deal.
Only minutes after her graduation she signed herself over to the Atlesian military and cut ties with Qrow.
Winter willed herself to keep a dry eye in front of him. She took his hand and pressed the ring into his palm. His rough fingers had curled over hers and he had asked her to stay. His eyes were a familiar, burning red, a color he only adopted in battle and when his emotions were not under control.
She swallowed, her throat thick, and said no. He pressed the ring back into her hand and said, his voice suddenly filled with resentment, that she could keep it.
"Maybe it'll help you find some humanity after Ironwood drills it out of you."
Winter rose through the ranks quickly, once again finding her place and excelling. She became Ironwood's second, a vital member of the Atlesian military.
She lost her position as heiress in exchange for a life in military. She gave up Qrow and in return was allowed to keep her name and the power it weilded.
And she was content. All of those sacrifices felt small in comparison to what she had achieved.
The ring hung around her throat, strung by a plain silver chain and tucked beneath her collar. She felt it's cool touch against her skin each day. It served as a quiet reminder of the cost of her success.
Years passed before she heard his name again. Ironwood began issuing reports of hunters and huntresses doing work for Ozpin. She found Qrow's name in one and she reached for the ring on impulse. It was easy to read about him, to watch his progress and whereabouts as a seemingly unaffected, indifferent party. She wrote the reports and issued commands from afar.
Then they came face to face.
She had regarded him with a stiff stance and wary eyes. He had only looked at her once and she heard him snort, saw him shake his head and curse," Fucking terrific."
He looked well, if not tired. His hair was beginning to gray at his temples, most likely caused by stress.
She wanted to touch the ring. It had become a worry stone if sorts, something she touched or held between her thumb when she became especially distressed.
She made a point to keep herself poised.
"Hello, Qrow." She greeted.
He inclined his head in a mock salute and said in return, "Ice Queen."
Anger bubbled in the pit of her stomach and her fists clenched in an attempt at restraint.
"I take it you two are familiar with one another?" Ironwood questioned, not immune to feeling the tension in the room.
"We were classmates." Winter spoke up.
Qrow snorted again, loudly and derisively. "Classmates that fooled around on a daily basis." He corrected.
"Qrow!" She shouted, glaring at him.
"For almost two years." Qrow added in, as an afterthought.
Ironwood cleared his throat. "Ensure that your previous relationship will not cause problems in the future. You two will be working closely from now on."
Winter tucked her arms behind her back, nails digging into her forearms.
"Understood, General." She said, voice tight.
"Not a problem." Qrow said, his gaze averting from her.
Thankfully, their interaction was primarily through letters and reports of his whereabouts and actions. Even in those he was infuriating, skipping on details and lagging on his submission dates.
She went almost another two years without an incident.
Weiss started at Beacon, and though she was proud of her sister, Winter resented the fact that she had endured the exact training regiment that she had experienced. Her sister had come out if training with a scar across her eye.
Winter wrote to her sister often and in return received letters about her sister's adventures and experience at Beacon. She had not made team leader as Winter had, a fact that drove their Father absolutely mad, and the title instead went to an unassuming young girl named Ruby Rose. Her team was compromised of two other formidable warriors. As she researched Weiss' team she noted, to her disdain, that one was a direct relative to Qrow, the other his step neice.
A confrontation was inevitable, but Winter held off on visiting until it became impossible to avoid seeing her sister and meeting her team.
The Vytal Festival was a tradition that Winter had always enjoyed. When she discovered her sister had progressed to the next rounds, she decided to pay her a visit.
It was there that she met Qrow. He was drunk, which had become very common with him, and she had been impulsive.
It had been disastrous, to say the least.
When she was alone in the privacy of her hotel room, she peeled off her clothing and stared at herself in the mirror. The necklace hung around her throat, chain falling down her chest, the ring settling between her breasts. She picked it up and studied it.
She wondered what would have happened if she had said yes. Said yes to him,said yes to staying. She wondered where she would be, what her life would be like.
She imagined she would be a huntress, and that they would have had a child by now.
She clenched the ring in her fist. No. She liked her life. She loved the military, loved what she did, loved feeling the exhilaration that being in command gave her. She was meant for this life.
But, she thought, rolling the ring between her fingers, that didn't mean she wasn't allowed to regret.
