Author's Note: This is my response to the prompt for the first day of the second Chair Week, future. It is set during season five circa pre-5x19 and maybe breaks the rules of Chair Week, but you can't fight inspiration.
"We'll type up the papers and courier them over for your signature tomorrow, Mister Bass," the man seated on the couch beside him says as he shuffles his papers and prepares to stuff them into his briefcase.
His associates nod their heads in agreement as they move to stand, and Chuck murmurs his thanks as the team of lawyers gather their briefcases and shuffle out of the room. He reaches for the glass of scotch on the table and raises it to his lips, but the eyes of the man wearing plaid and leaning against the doorframe with his arms cross bore into him and he pauses in his movements.
"Yes, Nathaniel?" He asks before taking a drink, before letting the liquid slide down his throat. It no longer burns him after years and years of partaking, but he likes the taste, likes the way it cleanses his palette of the terrible aftertaste left by a three hour meeting hammering out details and haggling prices.
"Are you sure you want to do this?" His best friend asks. "You can't buy her affection."
"I know that," he replies because he learned with two necklaces and a ring that buying her things will only get you so far. Because money may tie her to the House of Grimaldi, but he's watching her choose a pauper over a prince, over him. "That isn't what this is about."
He shakes his head at his friend's misguided understanding of what exactly he's doing as he reaches for the stack of newspapers on the couch beside him, as he pulls them out from under Monkey's belly and tosses them onto the coffee table. Her face would haunt him even if it wasn't printed on the cover of every magazine; his heart would beat to the rhythm of her name even if it wasn't printed in the pages of every newspaper.
But her face is on the cover of every magazine and her name is printed in the pages of every newspaper as the world fawns over her, over the American beauty turned Princess of Monaco. Special commemorative issues printed and hawked on every street corner with photographs of her wedding gloss over her declaration before the ceremony, her disappearance from the reception. And he is forced to see those moments each time he reads the paper or takes Monkey on a walk.
Yet no one sees what he sees. No one sees the tight smile she's perfected from years of make-believe, from years of pretending to be who others want her to be and suppressing the parts that make her beautiful and unique and perfect. And while the world coos over pictures from her honeymoon, over pictures of her shopping in Monaco, he watches her become more withdrawn and sullen with each passing day. She's a good actress but she has never been able to hide from him because he knows her, because he sees right to her core.
"I walked away. I told her to be with him because she was happy and she glowed and that is all I have ever wanted for her. And now she's not," he replies with a gesture to the array of photographs and newspaper articles. "So what else am I supposed to do?"
Nate sighs, moves away from the doorframe towards the couch to join his best friend. And the truth is that he doesn't know the answer, hasn't known since the accident what to do or say.
"But selling Charles Place? That was supposed to be your legacy, Chuck," Nate reminds him, but the last words of that sentence go unspoken and hang between him and his best friend. Because Charles Place was going to be Chuck's legacy – a legacy untainted by a decision to trade his girlfriend for a piece of property, by his supposed mother and his uncle scheming together to cost him the one thing that mattered. But he had been a child playing in an adult world and realized too late what that one thing was.
"And mortgaging the Palace? That's your father's legacy."
The reminder is unnecessary because he had thought long and hard about mortgaging the Palace, had fought with his team of lawyers over the decision. Yet the number of zeros demanded at the end of the check left him no choice. The Palace has a higher economic value than the Empire, and he cannot fight for the legacy of his father and fight for her future. It is one or the other.
And maybe having a legacy doesn't matter anymore. He still wants to succeed, still wants to prove to himself and his father and the world that he is not the screw-up, the lost cause so many believed him to be. But legacies matter only for those who are leaving someone behind, and that hasn't been in the cards for him since the town car slammed into a wall, since the future he dreamed up sitting beside her disappeared in the blink of an eye.
"This isn't like liquidating your shares in Victrola or paying the eighty dollar application fee to Columbia," Nate begins, but Chuck cuts him off because the price tag may have changed but the sentiment is still the same.
"Isn't it, though?" Chuck questions. "I did all that to help you, to help her because you are my best friend and she – she's the love of my life. At the end of the day, your happiness and her happiness is all that matters."
The truth of his words smother Nate like a heavy, wet blanket, silencing all arguments against Chuck's decision because there is nothing he can say to change the way Chuck feels. He watched Chuck let her go over and over again – stepped aside so she could go to prom with her childhood sweetheart and encouraged the love of his life to be with Louis. And now Nate is watching Chuck choose not to fight her attraction to Dan and choose to nearly bankrupt himself for her freedom because he does love her, because he only wants her to be happy.
"I want her to be happy, and this contract – this dowry prevents that." Chuck explains. "If I have to sell everything I own, give up everything so she can have the freedom to be happy, to decide her future for herself, I will."
"And what about your future?" Nate questions. Chuck swirls the glass of amber liquid in his hand, watches the ebb and flow with the movement before raising it to his lips and drowning the contents of the glass. He lowers the glass to his lip and continues to stare off into the distance.
"If two people are meant to be together," he finally says after a long pause, "eventually they'll find their way back."
"Do you really believe that?"
"I have to," Chuck replies solemnly. "I can't imagine a future where I won't love her, where the pull between us is deniable, where she and I stop being Chuck and Blair, Blair and Chuck."