Nicknames: T, anything really, Troystopher (only by Charlie)
Character Age: 38
Height: 6 ft
Parents: Edmund and Victoria Windsor
Siblings: Charles Edmund Windsor III
Occupation: Attorney General of the State of New York
Birthday: December 27th (Capricorn)
Faceclaim: Theo James
Hometown: NYC
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Character Inspiration: Lucifer Morningstar (Lucifer), Sebastian Valmont (Cruel Intentions), Elijah Mikaelson (TVD), Logan Echolls (Veronica Mars), Derek Hale (Teen Wolf), Ryan Atwood (The OC)
tldr;
– TROY WINDSOR had always had it all, until he didn’t. He grew up in a family of lawyers, therefore he always felt as if he had his future already planned out for him. It was a surprise to no one when the only child ended up in Law School. What was surprising though was when he married right after graduation. His job was something was great at, but never loved it, his heart laid with his wife and son. Until the night of the accident; where Troy not only lost himself but his family. A hit and run had left the DA at the time all by himself. This was when he realized the power that he could have and how he ended up as the Attorney General just a few years later. Gone were the family nights and soccer practices, turned into late nights of drinking, lust and mornings that started with popping pills for breakfast. A profession that he’d despised became an easy escape, he had so much power and so much and so little to lose that he used his position to his advantage and often chooses the highest bidder when it comes to the gangs, some would call it being smart, others call it a path to self-destruction. The past year Troy found love again, and he's not navigated it well, but recently, he feels as if his life is taking course again - almost if he now has a second chance.
READ BELOW for fun facts, biography, possible connections.
biography
TW: drugs, car accident
troy was born and raised in NYC. His father, a lawyer like most of the side of his family and his mother a wannabe actress that never really made it to hollywood, but that seemed quite happy when both her boys were born and decided to simply be their mother
growing up, troy mostly saw the good things in life. he was a lucky child, that saw real love between his parents despite how dysfunctional their relationship could be. no marriage was perfect but Edmund and Victoria were a team, through everything
after many catholic boarding schools, Yale felt like a breath of fresh air and troy didn't take it for granted. he had fun, and eventually, he found love.
marriage happened right after college, soon after he was working in the DA's office. troy never really loved his job back then, it was more something that he did because it was expected of him. but he was good at it, so good that he began to move up in his department with time.
he was already a district attorney by the time that his son was born and it felt like a blessing; a fairly easy job that allowed him to spend time with his loved ones, he couldn't really ask for more. his family, at one point, had become his entire world.
until one night, five years ago, when they were driving back from a work event and a car ran a red light. it hit them hard enough to turn the car upside down. when troy woke up hours later, he was the sole survivor.
since then, troy has struggled to find a purpose in anything that he does. he couldn't figure out what happened back then and to this day, has yet to find the person behind the wheel. it almost feels like he has gone completely.
before this, troy's knowledge about the gangs came solely from his brother's, Charlie, involvement in them - the youngest windsor had always known to look out for him, where he could help, even when he was still a relatively clean member of law enforcement
it was this accident that allowed him to see how much power he could hold with his job. what had once been a profession that was instilled in him at a young age, became everything to him. he could hire people to look for answers, and in the process, he could get things from them as well. with money, all the small vices from his college days came back in full force
while his drive to work with the organizations initially came from his path of self-destruction, nowadays troy found multiple connections that make emotionally invested in their safety: his brother, the biggest one and then a man that eventually became a part of their family. he will work for any gang but will always be partial to his brother, just won't say it out loud
random facts
went to a few catholic schools growing up, got expelled out of one and he can't remember why
still wears his wedding ring, but on his right hand
loves spending money, especially on clothes
addiction problem remains, though lately he's found himself trying to let go of it, still feels attached to the feeling
loves reading and art and will come off as very pretentious (also another thing he spends millions of dollars on probs)
can be very calculating, but is also very easily distracted
will do anything for charlie and those he considers his close friends
obsessed with esra durmaz - a feeling he never thought he'd be able to have again
possible connections
work related: he was an ADA, then a DA so he did the court system for years. so lawyers, detectives, maybe civilians involved in some of the cases that he prosecuted. could be positive or negative connections, very open.
business: when it comes to the gangs, he really doesn't care. his office is open for anyone willing to pay good enough and/or to service him in any way. he keeps his options open and while sometimes probably picks and chooses, the only person that he ultimately is loyal to is no one but himself. that could change, who knows.
ex-party friends, and still party friends: he's been a mess the past five years. his image is very clean to the public eye, but he definitely attends parties, clubs and simply knows how to hide it all to keep his reputation in tact. opportunities are endless, maybe they hate each other because troy is a douche or maybe they have used his lil secret against him, or maybe they're simply just friends that party?
past flings/hook ups/exes: self-explanatory. was married for a long time and then his wife passed away, so anything in the past five years has probably been kind of rocky, lots of ups and downs, and very confusing (at least for him)
enemies: whatever comes to mind really, could be for a reason, could be personalities don’t match, he's probably crossed a lot of people in his lifetime, actually so go wild on this, etc.
+ anything that comes to mind, could be drug dealers that his supply stocked, work friends, people that he basically drinks with, etc.
It's inexplicable. The lingering tether between them despite standing several yards apart, separated by the endless expanse of pool and too many mingling bodies to count. Or how Esra feels his eyes on her before ever managing to sneak a glance in his direction. The one she does shoot him is quick and discreet, hardly noticed by the two influencers who were attempting to coax her into a business partnership. Attempt being the key word as her interest in the collaboration waned with every passing second, although her expression refused to betray said boredom.
Then, as if she summoned him by pure will, there Troy stood in the midst of their conversation. All effortless charm and commanding authority, dispersing the two women with little more than a passing remark. No stranger to how unmistakably gifted his appearance was, when their eyes widened slightly before scurrying off, Esra almost smirked. The ghost of it still dances across her lips while she turns to look up at him properly. Sunlight breaks across his face in the form of a smile and she mirrors it with her own, shameless and clearly infatuated as he admits to the lie.
"You almost gave the blonde one a heart attack." Far from chastising, her voice carries obvious notes of amusement. "Even with the glasses." Gingerly, she reaches up to remove the designer shades from his face, searching for the only pair of eyes that actually see her. It was a miracle that she managed restraint with him for as long as she had— now it all flew out the window with careless abandon. "I don't think I can endure another two hours of socializing." Not when she knew their presidential suite sat blissfully empty upstairs. Away from the crowds. Away from the world.
"Don't sound so surprised," By his effect on people, that was. She was, or had been, almost immune to it - to him - for a long time. Though a part of him was certain that she was just good at hiding it. Optimistic and delusional of him. It didn't really matter, for at the end of the day, Esra had finally looked at him how he wanted her to. To think of the last time they had both worn white as the beginning of their relationship would be accurate. That was the moment when Troy realized he did not want to be who she thought he was. And now he can't picture his life without her guiding him in way more ways than she is even aware of.
Using his hand on her lower back to being her closer after she rid him of his sunglasses, he leaned in for a soft kiss; not a care in the world about the people around them. "You want to ditch?" His tone is playful, and more on the side of unbelievable but there's no real bite or shade behind it. Rather, he knows her friends organized this event, a part of him thought he would ask her to leave. Puling back just enough, Troy looked around them, for the first time in a while there seemed to be less tension than at other events. It would be a waste not to disappear into their own world not just for the night but the entire weekend, honestly. Suddenly, he's looking for an exit strategy.
Where humour might have existed in the karaoke situation, there was none on his face. It belonged, as far as he was concerned, in a category of stupid and nothing else beyond that. "Also had the braincells to check the weather forecast for the day." Cami wouldn't have missed a detail, he was well aware. Add that to the stationing of triple security that historically did the trick, though he had lost the ability to rely on people not succumbing to blackmail tactics. No matter how loyal someone was, the examples were right in front of his eyes - everyone had a weak point if pressed upon hard enough they'd react to. "Charles has his hands full for the evening, anyway." His chin tipped lazily towards where Charlie stood with his date - his drunken date, that was - somewhere within the crowd. As for his sister, he was well aware right where she was. "Vicky doing her summer in the Hampton's this year?"
Troy barely chuckled at the mention of the weather. It seemed almost silly now, thinking back to the private island event and everything that could have possibly gone wrong with it - going wrong that night. Granted, Celestina and Camilla knew what they were doing, not their first rodeo and whatnot, so he wasn't surprised at all. His gaze moved back to his brother, entertaining Alix Harrigan, an easy smile appearing on his face. "At least for the next hour." They made so much sense, sometimes it surprised Troy. Charles Windsor III was one of a kind, and so was Alix, for them to find each other as effortlessly as they had seemed surreal. "Yeah, you can't get her out of here until after Halloween. Retirement life hates to see her coming."
"Is that what they say? Are you the wicked one? I remember seeing Wicked on Broadway, that was fun." It was almost like a word association game for Rachel, she was pretty sure that he was still following along, but she wasn't totally sure. If she was slightly more sober, she might question what he meant a little bit more by there not being rest for him. Obviously she knew about the fires, and honestly in general New York was probably an insane place to be an AG. "Somewhat, actually...I mostly know of them from Esra. Big fan of her, by the way. How long have you guys been together?" She didn't know if he felt any type of discomfort with her asking about his relationship, though it wasn't like she was asking some jealous ex, but rather just curiosity as a friend.
"A classic," Not that musicals were places he constantly sorrounded himself with - hard to miss a big one though. However, it seemed to track for someone that existed in the journalism word, someone like Rachel. Troy didn't even try to hide his smile as the woman brought up Esra, for he had never really bothered to hide their relationship. Neither of them ever had, not even when they weren't together; the two had been to so many events together anyway, by the time they really began dating, everyone half-expected it. "Since last November." Technically, it was longer than that, but he had been to blame for their short break after the gala at the museum, therefore he always counted from that day in his office, when Esra had approached him and out everything on the line with only a few words. He tilted his head to the side, wondering how well she and Esra knew each other. "Are you still not wanting to get back to journalism?"
"This is a pretty immaculate hotel. I feel like if I squint I could almost pretend I'm in France. Or maybe just have one more glass of this." She raises the glass of wine she was having, unsure what number glass she was on. Enough for her to feel no qualms about chatting it up with anyone, but also not enough for her to be slurring her words. It was the perfect in between where she was still fun to be around and her cheeks were slightly pink. "How have you been? I feel like it's been awhile since I saw you."
Troy managed a small grin at Rachel's words - always finding her views of the world almost amusing. They weren't the same people that they were in college, that much was clear. Their lives had different purposes, and yet, he still kept in touch with her. Since the Pantheon text, Troy did wonder how she was involved in this darker world that surrounded them - and now here she was, a retired journalist at a Mob event. "No rest for the wicked, as they say." Though it wasn't himself he was referring to, but the anonymous entity that had made his role as the Attorney General entirely too difficult and almost pointless. Helpless. "Do you know the hosts?"
"Don't worry, I think Cami and Cel hid all mics to avoid another karaoke scene." Troy murmured teasingly as he found an empty seat next to Aslan, his glass of whiskey placed on the table. Unlike a few months ago, when Troy had used a party like this as the perfect excuse to get shitfaced, he had been nursing the same drink for the past hour, not even intending on finishing it. Esra would never live down the karaoke fiasco from the masquerade a few months ago - mostly because it was hilarious, even if all the singing had been courtesy of Troy's own brother. "But we should probably keep Charles and Esra away from each other just to be safe."
The sea of people wearing white did nothing to erase the rush of recognition when Troy found himself reminiscing of another time when both he and Esra had worn white. The memory is still clear as day even if it has been longer than a year and there is a stark difference in who they were to each other while they stood on the yacht - his jacket covering her shoulders after the night had went wrong - and who they are now. His Brunello Cuccinelli sunglasses do little to hide his gaze as it lands on Esra while she stands on the other side of the pool, chatting away with Troy hasn't paid enough attention to recognize from this far.
He merely mumbles a goodbye to the Councilman that has been talking his ear off for the past fifteen minutes, deciding the mingling portion of the evening was coming to a close and making a beeline in his girlfriend's direction. "Cel needs you for some pictures." Troy announces to Esra and her companions, his hand finding its place on her lower back. A lie entirely for his benefit since he wants her all to himself as usual. It takes seconds for that to happen, and he smiles. Despite dating now, Troy can still see the same woman that stood before him last April and made him question everything about himself - now he knows her even more, and it's surreal, how much he admires her. "Cel doesn't need you for pictures, but I needed them gone."
Perhaps she was, well intentioned jest or not. To an outside perspective, surely her behavior over the last year read as entirely off-kilter and erratic to a concerning degree. Willing to put her fragile hopes on the line at the slightest provocation from him. Her seasoned and stony demeanor reduced to ash whenever he glanced in her direction, when he shot her with that entrancing smile — a reminder of how he'd unraveled this game long ago and simply waited, still waits, patiently for her to catch up.
But they both knew she had a propensity to overthink with him, to dwell on precise phrasing rather than speaking plainly. As if uncertain whether the slightest move, one too sudden or unplanned, might send them both skittering away into the dark. Thus I want to be with you as often as possible and I'm in this for however long you'll have me tumbled out as a real estate proposal instead.
Her lips part slightly to amend the statement when Troy approaches, looking positively elated and concurring without a breath of hesitation. The quiet uncertainty still coiled in her sternum unravels as soon as he's close enough to touch. "Immediately?" Her gaze drifts from his eyes to his mouth and back again with faint amusement. "I suppose it does seem urgent. My career is on the line." She's covering the obvious sentiment and curbs that instinct before it goes any further. Pushing up onto her toes and wrapping both arms around his neck, Esra kisses him deeply for a long moment to reaffirm that this means far more to her than any ease of logistics.
"Thank you." Not for his permission or his instantaneous agreement. Rather for being unequivocally himself, for making the entire conversation so simple it seems almost ridiculous to have allowed herself even a flicker of concern. And then for all the ways in which he's learned to read between the lines. Absorbing context from the gaps. Finding unspoken words written on her face, instead of taking everything she says at face value.
What a bizarrely wonderful thing it is to be known.
"Caprese..." The answer came without thought as she dug into a large work bag set out upon the vanity, eventually sighing in defeat because the missing item simply wouldn't materialize despite her best efforts. "I left Kimmel's file at my place and we have a meeting at nine tomorrow." Which meant waking up even earlier to swing by her house before heading into the office, effectively decreasing their already limited time together. Inconvenience upon inconvenience when it came to morning logistics and, more selfishly, disrupted their semi-slow mornings together. A life balance ritual that had become rather sacred in her book. Brows threaded together as she ran through eight different scenarios to get out of this knot, but each one reached the same inevitable conclusion and that alone made her readily accept the waiting glass in his hand.
As she sipped, dark eyes swept the bedroom, absorbing the myriad of ways that she had slotted into his home. Evidence of her life seamlessly blurring into his was dotted throughout every room. Her charger on the nightstand, shampoo in the bathroom, an assortment of clothes hanging in his closet as if they'd always resided there. Esra couldn't readily recall the last time she'd even fallen asleep without him at her side— not since November at least. It felt a little foolish then to keep an entirely separate home for... what purpose exactly? Future headaches to mimic this one? The illusion of her requiring independence? As if they weren't emotionally bound to one another in every way that mattered.
What is really stopping us from doing that?
His question from the car echoed louder this time, reverberating through her mind as the idea crystalized and took hold. They'd never discussed it outright, neither of them willing to pressure the other into moving faster than necessary, but now seemed as good a time as any to broach the long awaited subject. "What if I sold my house?" Her gaze returned to him, hovering with anticipation. "It would make things easier if we didn't have to sprinkle a little bit of ourselves in both places. No more bouncing back and forth or deciding where to go." Meant to soften the enormity of the subject, although Esra realized after staring at Troy for several beats that she simply just wanted to live with him. "Tell me if I sound insane."
For someone incredibly observant, Troy did not notice his girlfriend's far away look after giving her the glass of wine, for he simply walked further inside the room and sat down on the bed that was now, basically, their bed instead of just his. Though they shared their time between their homes, usually depending on which house was closer to their locations, his was more often the culprit because his job needed him at the office way more often than hers did.
Naturally, when Esra's words left her lips, and Troy processed them, he only turned his head to look back at her.
"What if I sold my house?"
She sounded insane. Mostly because she didn't need to sell her house, they could keep both. Unless she really wanted to sell. But he was fairly sure that what he needed to focus on, right then and there, was the fact that Esra Durmaz was alluding to moving in with him. The penthouse that he currently resided in was fairly new, Esra had been there with him while he chose from a long list of options, for he had managed to let go of the home where his only child and late wife had lived up until their last breath. In a lot of ways, it was already theirs.
"You sound insane." He started, but in seconds his smile appeared in his face, almost taunting her. If it weren't for the fact that Troy was just ecstatic. "You don't have to sell your house." Troy admitted lightly as he moved to stand up, joining her by the vanity and her work bag - and her attempts at finding a file that clearly was at her place. He tried to hide just how giddy he was at the idea of having her around even more often - permanently. Tried was the keyword though, since it was written all over his face as he spoke up, "unless you want to, of course. You can move in here whether you sell it or not though. And I think you should move in immediately, actually, so this file missing thing doesn't happen again and whatnot."
"I'd be a fool not to acknowledge the organized crime that moves about in the city. I knew that. You knew that. I think anyone with a clear head on their shoulders knew that. Knows, not just past tense but it's felt different lately. Before I knew what I was up against. No who, they don't exactly hand out member lists or business cards, but now it feels... unnerving." That was the only way she could put it, in order to summarize how it felt. Crime was as old as humanity itself, from smaller things to what it was now. That had always been the case and although she disliked it, she couldn't very well fool herself into pretending that wasn't a thing.
Val leaned back against her own chair, the frustration evident yet pushed back down for the moment. A question of strategy. "All of this is entirely speculative. I don't know what I am up against, we are playing chess blind. But based on that, I have to assume that these people, whoever is pulling the strings have their reason. What do they gain from this, any of it. How do you play against someone who does not seem to be in it for personal gain. Well, what we might define as such. Or perhaps their personal gain is something we can't see." Honestly, the chaos had her stumped for answers. Normal logic did not seem to apply since from all the case files on her desk, none of them seemed to indicate wealth as an option. "Control or chaos. Before long we're up against someone just wanting a laugh." It was nothing more than a throwaway comment. ❧ @troywindsor
Troy sat silently as Valeria's short speech seemed to go off for hours. If she was aware of what was happening in the city, then she wasn't being productive enough with her time to let the people of Manhattan know it. One look at the news and it was hit after hit taken for their office and law enforcement - granted Troy helped the very same people that were running the city's underground more often than not. But he knew how to look worried and preoccupied. "It doesn't matter who we're up against, Valeria. You are the District Attorney, you should have answers even if they're bullshit." He reminded the woman with a small frown. "So what's your plan and how can I help?"
"do you think this means something?" after she'd made her order and wandered down toward the collection area, lola found herself in the same space as someone she'd used to see with some regularity. "it's been... what, how long?" somewhere in the region of a year but the nurse didn't trust her memory on that fully so she left it up to troy to fill in the blank there. "unless you're someone that believes in coincidences..." clearly, by the way lola had stated that meant that she did not. "seems the universe thinks we're not done with each other." someone squeezed between them to collect their drink order and she somewhat grinned at how rude and impatient people could be, then regained ground near troy. "how've you been? been seeing someone else, have you?"
The Attorney General pulled a move that he hadn't used in what felt like years - he kept his sunglasses on as Lola made herself known to him. Not too long ago, the woman had been almost a permanent name on his contact list; once or twice a week, they'd meet up and exchanged money for whatever goods she had on her or a special order for one of his parties. "You could say that," He was all charm, despite choosing to keep his sunglasses on for their interaction, not that he thought they were enough to hide him from the curious eyes if they recognized him from the news channel. "Coffee is my newest addiction, if that tells you anything."
Technically the windows of a high rise, especially one as tall as his, weren't meant to open. Safety reasons, air pressure differentials, whatever the contractor had droned on about when Jamie hired them to make sure at least one could be cracked for this very purpose: exhaling cigarette smoke through a narrow crack into the already congested New York air. "You know, I remember a time when we used to be fun." Well, attempted fun in the wake of Troy's life imploding six years ago. Back when his oldest friend longed for little else beyond self-destruction and Jamie would've walked through fire if it meant keeping an eye on him through the drug spiral. "Now it's all overpriced dinners and bedtime at eleven. Either we're becoming old or you're becoming boring and I'm catching it by proximity."
Troy just smiled, taking a sip of his drink. "I can't believe you miss me in my crashout era." He joked lightly, though he understood what the other man meant. Troy had this issue with finding limits - had always had it, really. He was either all in, all the time, or completely out of it, ever. Addictive personality is what he'd heard his parents call it as he grew up; before his life had completely changed as an adult. Something had triggered it, and he and everyone close enough knew exactly what nowadays. People like Jamie, who'd always been around. Sometimes he had wondered if he would get out of that cycle, and somehow, now he had. "Hey, we opened the windows of your high rise, some would consider that a suicide missions. We're not as boring as you're making us out to be."
