Chapter Text
Hailey knew in many ways that she was luckier than most people. She'd gotten a good education, which had led to a good job, her dream job. One where she was surrounded by good people. And sure, her childhood was…less than ideal, but she also knew it could have been a lot worse. There was one thing, though, that more than gave her a leg up in the world. One thing that not many people in her life knew about. Hailey was rich.
Her Grandfather, Yiannis, had been a stockbroker. And a really good one at that. He owned his own firm, and until he retired - and sold the business for a mint - it was one of the top-rated brokerage firms in the midwest. And while Yiannis knew that there were more important things in life than money, like family, passion and love. He also knew that not having to worry about money made living, thriving and growing easier. So when his grandchildren were born to his only child, his daughter, Arianna, he set up two trusts. One was dedicated to the child's future education should they choose to go to college or university. The other was left in a trust, set to accrue and grow in a series of investments until they turned twenty-one. Then it was theirs to do with what they pleased.
Until she was eleven, Hailey and her family lived with Yiannis in Lake Forest. One of the many affluent suburbs of Chicago. They lived in a big house he'd bought specifically to have his family live with him. Because, after all, as he always said: money is nice, but family is paramount. Though as she grew older, Hailey couldn't help but wonder if it was really just a way to keep an eye on her father. To stop things from getting as bad as they did. Because after Yiannis died, her life changed forever.
Her Grandfather hadn't been sick, but he was a man in his late seventies. He simply went to bed one night in mid-August and didn't wake up in the morning. It had been sad. But ever smart with his money Yiannis Andino had been prepared and did everything he could to make the process as smooth as possible for his family. His funeral had been planned, funds had been set aside, and everything was prepared for probate. And that is when things in Hailey's life really started to change.
Yannis had left very clear instructions in his will. All his money was to be split between his four grandchildren. It was to be added to their trusts to accrue in value. His daughter and son-in-law would have no access to the money. Not unless the kids wanted to give them some or all when they came of age and were free to do with it what they wanted. The only thing that Arianna and Nik got was the house.
Hailey's father had been counting on the inheritance he thought his wife would receive. He had plans for that money, all of it. Big plans about what to do when the 'old bastard' finally croaked, and Arianna, and by extension him, got what he thought they were owed. So he was furious when he found out they got nothing. Sure there was the house; it was a nice one, worth a lot of money, especially before the bubble burst. But it was still pennies compared to what he'd been expecting. Compared to what his children would eventually get.
But Hailey didn't really understand that, not at eleven years old. Didn't understand why her father was so bitter. Why his drinking had become worse and worse. Why his anger, which was always so close to the surface, finally seemed to boil over and never stop. What she did understand was that they were moving. They sold the house in Lake Forest, and all the money went into the restaurant her father bought in Greektown.
It wasn't what Nik wanted. It wasn't the plan, the dream. That had been a fine dining establishment. One with white linen table clothes, candles, atmosphere, and maybe, hopefully - eventually - a Michelin star or two. A cooking empire, something akin to Wolfgang Puck or, even better, Gordon Ramsey. Instead, all he got was a diner.
Now it was a good diner. A popular one that did steady business and was a fast recommendation amongst the locals. And that was a saying something in the oversaturated restaurant market in Greektown. And sure, some years were leaner than others. However, money remained something the Upton family didn't have to worry much about. They were lucky. But it still wasn't the dream, and Nik made sure his family knew that.
Once she got older and had a better sense of what was coming to her in a few years, the money and the freedom that would come along with it, Hailey longed for it. So she worked her ass off to have her pick at universities. And she did. To schools all over the United States and Canada. But she couldn't bring herself to leave Chicago. She stayed on campus, lived in the dorms, and only visited home when she absolutely had to. Her father had wanted her to be a lawyer, and Hailey thought she wanted that too for a while. But not a corporate lawyer like her dad wanted her to be, no doubt so she could find a loophole in the trusts her Grandfather had set up so long ago. After all, he'd paid several lawyers a lot of money over the years to try and do just that. No, her interest was in the criminal justice system. And then, in the middle of her Early Theories of Capitalism final, in her second year, she realized that it wasn't what she wanted. She didn't want to be a lawyer; she wanted to be a cop, she always had. So that's exactly what she started to plan for.
Then on her twenty-first birthday, after she'd already applied and been accepted to the Academy for the fall session, Hailey got a call from the brokerage firm. She was of age now. She had access to her trust. And it was time for her to learn what that really meant.
Her eyes went wide, and her ears went fuzzy as the broker explained to her and her twin brother Paul exactly how much money they now had. It was a lot. Like a lot, a lot.
"Now," the broker said once their shock was cleared. "Mr. Andino left instructions for you, what he thought would be best for you going forward, and the advice is still sound. But it's your money now; you can do whatever you want with it."
"What was Granpa's advice," her brother asked. Hailey's brain was still processing all the zeros.
"That we set you up with a monthly allowance," the broker replied. "Everything else we keep as it is, the trust will continue to grow, the investments we can move around as you wish and as the market changes."
"I-I don't know anything about investments and stocks," Hailey finally found her voice.
The man smiled, and it reminded her a little of her grandpa. "That's alright; it's why my job exists. We're at your disposal."
"But you agree with our Granpa," she asked. "About the allowance and everything else?"
"I do. Believe me, the monthly allowance is generous."
"How generous?"
"Ten thousand."
Hailey's jaw hit the floor again. "A month?"
"That's right."
The broker went on. He explained how the taxes on the money would work and how they handled investments to this point. What might be smart investments in the future, and what they're currently invested in that might be worth pulling out of sooner rather than later. "All things to talk about down the road," he assured. "This just gets the idea of it in your head for now."
He wrapped it all up by saying that they'd be set for life if they were smart about their money. "What does that even mean," Paul asked.
"Honestly?"
The Upton twins nodded in unison.
"If you leave this room today and decide that you don't want to work. Then you don't have to. You can live a comfortable life with the money you'll get from the trust. It's not what I would advise, of course. But I won't lie to you and say it isn't an option."
It wasn't an option that Hailey was interested in. She had applied and been accepted into the next Academy cast for the Chicago Police Department, and she intended to go. Paul had joined the air force right out of high school, and he loved it, and he'd built a decent career already, so he wasn't about to give that up either. So they stuck to their allowance.
It helped. It was nice to not worry about money. But honestly, it was too much. So Hailey found a better use for the money: charity. Local hospitals and schools. Cancer research. But most frequently, generously and always anonymously to the Chicago Police Foundation, to be spread out through the various charities the department supported.
The biggest thing Hailey spent her money on was rent. And even that wasn't extreme. Sure it was nicer than someone her age and at a similar stage of their career should be able to afford, but it wasn't some lavish luxury penthouse in the Gold Coast either. At their yearly meetings to discuss the state of her finances, which were always fine, the broker always told her it was smarter to buy than to rent. But Hailey resisted. It wasn't even that renting is what twenty-somethings did, so doing it made her feel like she fit in better with her peers, even if the crush of making rent was never something she'd feel. She wanted to wait until she found a place that felt like home. Just like that house in Lake Forest had been. Like no place had ever felt since.
So she kept searching for it.