Maybe that’s why you’re the only one who still interests me, Nathan. Preston and Mallory never understood those chess games. Preston was too busy shadowing Grandfather at the office, learning about profit margins and tax shelters.
He’d gotten his MBA from Wharton, Grandfather’s alma mater, and never let anyone forget it. Every family dinner turned into Preston’s personal TED talk about market optimization and strategic acquisitions. He spoke in buzzwords and PowerPoint slides, turning every conversation into a business pitch.
Mallory took a different approach. She turned herself into a brand, chronicling her life as the shipping heiress on social media. Two hundred thousand followers watched her pose on various boats, in various designer outfits, at various European ports.
She called it building her platform, but really she was just spending Grandfather’s money while waiting for more. Her biggest achievement was getting a blue checkmark on Instagram and dating a Swiss banker who owned a vineyard. Vernon and Beatrice, Preston and Mallory’s parents, were the ultimate power couple in the most hollow way possible.
Vernon had worked his way up to CFO of Whitmore Shipping, though most of the real work was done by his assistant. Beatrice spent her time at charity galas, not because she cared about the causes, but because she liked seeing her picture in the society pages. They lived in a house so big they needed an intercom system to talk to each other.
And then there was me, teaching 43 teenagers about the Constitution, grading papers at a kitchen table I bought at a garage sale, and feeling more fulfilled than any of them could imagine. That was my life before the funeral, before the envelope, before everything changed. I thought I knew who I was and where I came from.
Turns out I was watching the wrong pieces on the board all along. The Rochester Country Club had never felt more suffocating than it did that October afternoon. Grandfather Roland had specifically requested his will be read here, in the same oak-paneled room where he’d negotiated his biggest deals over brandy and cigars.
The mahogany table reflected our faces like a dark mirror, and I could see Preston adjusting his Rolex for the third time in five minutes. We’d just come from the cemetery, where the autumn rain had turned the burial into a muddy mess that Beatrice complained about the entire ride over. Before we begin, Mr. Harwick, the family attorney, adjusted his wire-rimmed glasses and cleared his throat.
I want you all to know that Roland was very specific about these arrangements. He reviewed this will one week before his passing. Vernon leaned forward, his hands already forming fists of anticipation.
We understand, Harwick. Roland discussed the succession plan with me extensively. That was a lie, and everyone knew it.
Grandfather never discussed business outside the office, and he certainly never promised anything to anyone. But Vernon had been telling anyone who’d that he was taking over as CEO, that Preston would be his right hand, and that the family legacy was secure. Let’s proceed then.
Harwick opened the leather-bound folder. To my eldest son, Vernon Whitmore, and his wife Beatrice, I leave the estate in the Hamptons, and the investment portfolio contained an account ending in Fort 471. Beatrice grabbed Vernon’s arm, her diamond bracelet catching the light.
The Hamptons house. Oh, Vernon. He did remember how much we loved it there.
To my grandson, Preston Whitmore, Harwick continued, I leave Whitmore Shipping Industries and all its operational assets, with the condition that he maintains current employment levels for at least one year. Preston stood up so fast his chair scraped against the floor. I knew it.
Grandfather, I won’t let you down. He was already pulling out his phone, probably to update his LinkedIn profile to CEO. To my granddaughter, Mallory Whitmore, I leave the Manhattan penthouse on Central Park West, and the yacht, Serenity, currently moored in Newport.
Mallory let out a squeal that could have shattered Crystal. The penthouse? Oh my god, do you know what that’s worth? And the yacht? My followers are going to die. Mr. Harwick turned to me, and I saw something in his eyes that looked almost like pity.
And to my grandson, Nathan Whitmore, I leave this. He pulled out a small white envelope, worn at the corners, my name written across it in Grandfather’s shaky handwriting. The room went silent for exactly two seconds before Preston started laughing.
Are you serious? Preston’s voice cracked with amusement. That’s it? An envelope? I took it with steady hands, though my heart was pounding. The paper felt thin, insignificant.
Inside was a single plane ticket. Rome. One way, departing in forty-eight hours.
Let me guess. Preston snatched the ticket from my hand before I could stop him. A coach ticket? Oh, this is rich.
The teacher gets a vacation. Mallory was already recording on her phone. This is actually hilarious.
Nathan, your face right now. Don’t worry, maybe he left you some frequent flyer miles, too. Vernon stood up, straightening his tie with the authority of someone who’d just won everything.
Roland always said you lacked the killer instinct for business, Nathan. At least he gave you something nice. Rome is lovely this time of year.
It’s probably his way of saying good-bye, Beatrice added, her voice dripping with fake sympathy. A little trip to help you process everything. How thoughtful.
My mother, who’d been silent in the corner, finally spoke. Is that everything, Mr. Harwick? That concludes the distribution of assets, Harwick replied, closing the folder. There is a personal letter for Nathan, to be opened only upon his arrival in Rome.
A letter? Preston was practically howling now. What’s it gonna say? Sorry you’re poor. Enjoy the pizza.
Preston, enough, Vernon said, though he was smiling. Nathan chose his path. He wanted to be a teacher and Roland respected that enough to give him a parting gift.
We should all be grateful for what we’ve received. I looked at the ticket again. October 15th.
3 p.m. arrival. Alitalia flight 631. Why so specific? Why Rome? Grandfather had never mentioned Italy in all our years of chess games.
He’d talked about Shanghai, London, Hamburg, but never Rome. Well, I stood up, sliding the ticket back into the envelope. I guess I’d better pack.
You’re actually going? Mallory looked genuinely surprised. You’re going to use your sick days to take a random trip to Rome? Your grandfather gave me a ticket, I said, meeting each of their eyes in turn. The least I can do is use it.
Vernon shook his head. Sentimental fool, just like your father. Dennis never understood that emotion has no place in business either.
That’s when I knew I was definitely getting on that plane. Because Vernon was wrong about my father, wrong about me, and maybe, just maybe, wrong about what grandfather had really left me. The ticket weighed nothing in my pocket, but somehow it felt heavier than all the millions they’d just inherited.
As I walked out of that country club, their laughter following me to the parking lot, I remembered grandfather’s last words to me during our final chess game. The best moves, Nathan, are the ones your opponent never sees coming. The rain had stopped, and for the first time that day the sun broke through the clouds.
That night, I sat at my kitchen table staring at the plane ticket while my laptop displayed my bank account balance, $1,847.23. My rent was due in five days. My car needed new brake pads. I had forty-three essays on the Civil War to grade.
Every logical part of my brain screamed that flying to Rome was insane. But I couldn’t stop thinking about grandfather’s face during our last chess game, just two weeks before he died. He’d been different that day, softer somehow, like he’d finally stopped playing a role he’d been performing for decades.
Nathan, he’d said, moving his knight in a pattern I didn’t recognize. What do you know about trust? It’s earned, not given, I’d responded, the same answer he’d drilled into all of us since childhood. No, boy, real trust is knowing when to follow without understanding why.