The Longest Watch

The clock on the wall read 11:42 p.m.

Most people Noah Klein knew were either asleep or winding down with a book or Netflix. His apartment lights blazed like a ship lit for battle.

On the kitchen table:

A sprawling hex-map of the world’s oceans in 1799, printed in high-res and laminated like a museum artifact.

Laptops open to spreadsheets with labels like Quarterly Trade Revenues – East Indies.

Graph paper crammed with doodles of cannons, flags, and figureheads.

Dice—lots of dice—ranging from tiny four-siders to golf-ball-sized twenty-siders.

And at the heart of it: Trade Winds, the game that had devoured Noah’s free time and shredded his sleep schedule for the past three years.

It was like Dungeons & Dragons for history nerds—but instead of dragons, you had Dutch frigates; instead of enchanted swords, you had broadsides; instead of spells, you had the British East India Company’s chartered monopoly.

It was set somewhere between the late Napoleonic Wars and the Golden Age of Piracy—deliberately anachronistic in the name of fun—and it rewarded players for knowing their mizzenmast from their mainmast.

The five of them—Noah, Ravi, Sam, Theo, and Miguel—were in the middle of what was optimistically supposed to be a six-hour campaign.

They were already on hour four.

The Crew

Noah Klein – 24, grad student in history with a focus on maritime trade. Captain of the merchant Indiaman Leviathan. Strategist by nature, procrastinator by habit, fueled by Dr Pepper and stubbornness.

Ravi Sharma – 25, law student and Game Master. Master of the rules, the dice, and the drama. Enjoys adding weather events to sink ships “because it’s historically accurate.”

Sam Porter – 24, software engineer. Currently playing Commodore Étienne Dufort, a French privateer with a taste for British cargo and a record for never losing a ship.

Theo Byrne – 23, literature major, character actor at heart. Playing Seamus O’Malley, an Irish gunner-for-hire who’s perpetually drunk and perpetually muttering about rum rations.

Miguel Alvarez – 24, architecture grad student and the group’s unofficial historian. Plays João Batista de Carvalho, a Portuguese shipwright and occasional smuggler. Known for correcting everyone’s nautical terminology.

23:59 – The Plot Thickens

Ravi leaned back in his chair, grinning like the cat that caught the canary. “So, Captain Klein, you’ve just learned that the French have doubled their patrols around the Cape of Good Hope. You’ve got two holds full of silk and spices from Canton. What do you do?”

Noah sipped his lukewarm Dr Pepper and squinted at the map. “Do I have enough influence with the BEIC to get an armed escort?”

“You could,” Ravi said, dragging it out, “but it’ll cost you thirty pounds sterling, which is…”

“Too much,” Noah finished. “We’d barely make a profit.”

Theo tapped his pencil against the table. “Or we could go south, slip past Madagascar, and cut across to Bombay. Portuguese blockade’s lighter there.”

Miguel perked up. “Actually, in 1805 the Portuguese navy—”

“Historical accuracy is my favorite bedtime story,” Theo interrupted. “But let’s remember we’re not going to bed.”

01:00 – First Blood

An hour later, the Leviathan was in a running battle with Sam’s French 74-gun L’Inflexible.

Ravi narrated with relish: “The French flagship bears down on you, sails taut, cannons run out. The wind is against you, but your crew is holding steady.”

“Load chain shot at the foremast!” Theo shouted in-character. “Let’s see the Frenchies sail without their pretty sticks!”

Miguel, half in-character, muttered in Portuguese about shoddy French craftsmanship while rolling his patch check for the hull.

Sam rolled for Dufort’s counter-maneuver. “Eighteen!” he said triumphantly. “I cut across your wake and rake your stern!”

Noah winced. “That’s gonna hurt.”

Ravi grinned. “You lose four guns and half your mizzenmast. Crew morale drops.”

Theo slapped the table. “Crew morale can shove it—we’re still fighting!”

By 2:12 a.m., the Leviathan limped into Bombay with two masts splintered but her cargo intact. The French ship trailed smoke into the night.

02:30 – The Lull

Between battles, the atmosphere shifted.

The room’s harsh overhead light was off now; only the soft golden pool of the hanging lamp lit the table. Outside, the city was silent, save for the occasional whoosh of a passing car.

Noah’s laptop fan hummed quietly. The air smelled faintly of ramen and burnt coffee.

Miguel sketched in his notebook: a merchantman under full sail, the Union Jack fluttering. Theo hunched under his hoodie, munching pretzels. Sam leaned back, spinning a d20 in his palm.

Noah didn’t check the time. He didn’t want to know.

He thought about how these nights had become their ritual. No matter how hectic their weeks were—Ravi buried in case law, Miguel pulling all-nighters over CAD models, Theo juggling essays—they always carved out one night a month for this. They might be pirates and smugglers and merchants on paper, but in reality, they were just five friends sharing the same deck.

03:00 – Smuggler’s Run

Ravi tapped the table. “Dawn approaches in-game. The French blockade at Mauritius tightens. Captain Klein, what’s your move?”

Noah glanced at his cargo ledger. “We run the blockade.”

Sam laughed. “You’re insane. That’s half the French navy between you and open sea.”

“Better than letting the BEIC take my profits,” Noah said.

Dice clattered. Theo narrated storm clouds rolling in, lightning flashing. Miguel hurled Portuguese insults at imaginary ships.

The Leviathan took heavy fire, losing her bowsprit, but at 4:47 a.m., she broke into open ocean.

04:50 – The Dawn Patrol

The blinds began to show faint silver light.

Theo yawned. “Sun’s up.”

Sam groaned. “I’ve got class in three hours.”

Ravi stretched. “Worth it.”

Noah closed his ledger, looking around at his friends. They’d be zombies today—bleary-eyed, cranky, smelling faintly of ramen—but they’d also be telling this story for weeks.

Flashback 1 – Ravi’s Invitation

Three years earlier, Noah had been the new guy in the grad history lounge—awkward, clutching a stack of books on maritime trade and the British East India Company. Ravi had strolled in wearing a t-shirt that read Tell It to the Magistrate.

“You look like a man who can tell a mizzenmast from a topgallant,” Ravi had said.

Noah had blinked. “I… can?”

“Perfect,” Ravi said, grinning. “We need a captain for Trade Winds on Friday.”

Noah had no idea what Trade Winds was. By the end of that Friday night, he knew the smell of old dice and the joy of declaring war on Sam’s French frigate.

Flashback 2 – Theo’s Audition

Theo had joined later, when Miguel brought his “friend who does voices.”

At first, they thought Theo was too dramatic for the game. Then, in the middle of a boarding action, Theo slammed his hand on the table and roared:

“BOARD HER, LADS! RUM FOR EVERY MAN!”

From then on, Theo was their gunner-for-hire, Seamus O’Malley. Rum was optional; the yelling was not.

Flashback 3 – Miguel the Perfectionist

Miguel had been with Ravi since undergrad. He refused to play unless every map was to scale, every ship design historically plausible.

He had once paused an entire battle for ten minutes to lecture Sam on the correct number of gunports on a French 74-gun. Sam had rolled his eyes but changed it on his sheet.

Flashback 4 – Sam the Nemesis

Sam didn’t join to win—he joined to antagonize. His Commodore Dufort existed to make Noah’s life miserable. If Noah sailed east, Sam was waiting with a warship. If Noah sailed west, Sam had already bribed the local governor.

Sam called it “healthy competition.” Noah called it “piracy with paperwork.”

The Final Push – The Blockade at Mauritius

Back in the present—04:50 a.m.—the Leviathan was ghosting toward the blockade under cover of darkness.

Ravi: “You’re 10 nautical miles out. The French have five ships-of-the-line and three frigates forming a crescent around the channel. Roll for stealth.”

Dice clatter.

Noah: “Sixteen!”

Ravi: “They haven’t spotted you yet. Do you want to hug the coastline or go for open water?”

Theo: “Hug the coast—fog banks are thicker there.”

Miguel: “Historically—”

Theo: “We know, Miguel.”

They creep closer. Sam rolls for the French lookouts.

Sam: “Nineteen.”

Ravi: “A frigate peels off, cutting toward you. She’s faster and you’re carrying too much cargo to outrun her.”

Noah: “We’ll fight.”

The First Exchange

Theo rolls for chain shot.

Theo: “Eighteen—direct hit on her foremast!”

Ravi: “Her speed drops. She fires back with a bow chaser—three points of hull damage.”

Miguel: “I’m below decks, patching. Twelve on repairs.”

Sam: “Another ship-of-the-line moves in range.”

Noah: “Full sail—cut through the gap between them.”

Ravi: “That’s a high-risk navigation roll.”

Noah: “Roll it.”

Dice bounce.

Noah: “Twenty! Nat twenty!”

Through the Teeth

Ravi: “The Leviathan catches a sudden wind, slipping between the two French ships as their broadsides roar. Cannonballs smash the sea around you, but only one hits your aft quarter. You’re in open water.”

Theo: “We’re not out yet. Commodore Dufort’s not going to let us go.”

Sam grins. “You’re right.”

The Duel

Dufort’s flagship, L’Inflexible, bears down on the Leviathan for one last pass.

Noah: “I’ll fake to port, then swing starboard and fire a full broadside.”

Theo: “Risky.”

Noah: “Worth it.”

Roll. Nineteen.

The French ship turns too late—Noah’s guns speak, splintering her rail.

Sam rolls for counterfire. Fourteen. Glancing hit.

The Leviathan cuts past, catching the sunrise on her sails.

05:15 – The Aftermath

They slump back in their chairs as Ravi announces: “The Leviathan is clear. You’ve made it to Bombay with 80% of your cargo and 120% of your reputation.”

Theo claps Noah on the shoulder. “You mad, brilliant captain.”

Miguel adds, “And historically improbable, but we’ll allow it.”

Sam just grins. “Enjoy your little victory. I’ll be waiting next time.”

Epilogue – Sunrise

The light through the blinds is full now—gold and pale pink.

Ravi closes the game log. “Same time next month?”

Everyone groans in mock protest, but they know the answer.

Noah looks around at them—his crew, his rivals, his brothers-in-arms. In a few minutes, they’ll scatter to showers and classes and jobs, the day swallowing them up. But for now, in the last hush before morning fully claims the city, they are still at sea, still running the blockade, still laughing in the face of impossible odds.

Some people stay up all night for deadlines.

They stay up to rewrite history.