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The Best Laid Plans

Summary:

Barbossa has spent three months planning the perfect ambush—charts, calculations, tidal patterns, the works. Jack has a bad feeling. Barbossa dismisses it as paranoia. After all, mathematics don't lie, instincts can't be trusted, and Jack Sparrow has never planned anything successfully in his entire life.

When the plan falls apart in spectacular fashion due to circumstances even the most meticulous calculations couldn't predict, Jack finally gets the one thing he's wanted for years: the chance to say "I told you so."

He intends to enjoy every single moment of it.

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"I'm telling you, it won't work."

Jack leaned against the mast, watching Barbossa pore over the charts spread across the navigation table. The older captain had been at this for hours, calculating routes, checking tides, consulting that worn almanac he carried everywhere.

"And I'm telling you," Barbossa replied without looking up, "that it will. The mathematics are sound. The tides are favorable. The merchant convoy will be exactly where I've predicted, at exactly the time I've predicted, and we will relieve them of their cargo with minimal resistance."

"The mathematics," Jack repeated flatly.

"Aye, the mathematics. You should try it sometime. It's remarkably effective compared to your usual method of pointing at the horizon and hoping for the best."

"My method has kept me alive this long."

"Your method has gotten you marooned twice, killed once, and cursed more times than I can count." Barbossa finally looked up, that sharp smile playing at his lips. "Forgive me if I prefer a more... calculated approach."

Jack pushed off from the mast and wandered over to look at the charts. Barbossa had mapped out everything—the convoy's departure from Kingston, their likely speed based on the season's winds, the patrol routes of the Navy vessels in the area, the precise point where the Pearl could intercept without being caught in the crossfire.

It was, Jack had to admit, impressive work.

It was also wrong.

He couldn't explain why he knew it was wrong. The logic was sound. The calculations were meticulous. Barbossa had accounted for every variable Jack could think of and several he couldn't. By all rights, this plan should work perfectly.

But something in Jack's gut was screaming at him that it wouldn't.

"The intercept point," Jack said, tapping the chart. "Why there?"

"Because that's where the convoy will be most vulnerable. They'll have just passed through the Windward Passage—tired, complacent, thinking the dangerous waters are behind them. The Navy patrol will have turned back toward Port Royal. It's the perfect window."

"And if they're not there?"

"They will be. I've tracked this convoy for three months, Jack. They run the same route every time, like clockwork. Captain Whitmore is a creature of habit—he doesn't deviate, doesn't improvise, doesn't think." Barbossa rolled up the charts with practiced efficiency. "Unlike some people I could name."

"I improvise because plans go wrong."

"Plans go wrong when they're poorly made. This one isn't."

Jack studied him for a long moment. Barbossa was confident—not the false bravado of a man trying to convince himself, but the genuine assurance of someone who had done the work and trusted the results.

That was what worried Jack.

Barbossa was never wrong about the things he was certain about. Except when he was. And when Hector Barbossa was wrong, he was spectacularly, catastrophically wrong in ways that tended to involve curses, betrayals, or decade-long consequences.

"I have a bad feeling about this," Jack said finally.

"You have a bad feeling about everything."

"And I'm usually right."

"You're usually paranoid. There's a difference." Barbossa tucked the charts under his arm and headed for the helm. "We sail at dawn. Be ready."

Jack watched him go, that uneasy feeling still churning in his stomach.

He was going to regret this. He didn't know how yet, but he was absolutely going to regret this.

Dawn came, and with it, Barbossa's plan went into motion.

The Pearl cut through the water like a blade, her black sails full of wind, her crew moving with practiced efficiency. Barbossa stood at the helm, eyes fixed on the horizon, navigating by some internal compass that Jack had never quite understood.

They reached the intercept point exactly on schedule.

The convoy was not there.

"They're late," Barbossa said, frowning at the empty sea. "Whitmore's never late."

"Maybe he changed his route."

"He doesn't change his route. I told you—creature of habit."

"People change, Hector."

"Not Whitmore. He's been running this same passage for fifteen years. He'd sooner cut off his own hand than deviate from his precious schedule." Barbossa pulled out his spyglass, scanning the horizon. "They're coming. They're just... delayed."

An hour passed.

Then two.

The crew grew restless, shooting uncertain glances at their captains. Jack leaned against the rail, saying nothing, watching Barbossa's expression grow increasingly tight.

"Perhaps," Jack offered mildly, "we should consider the possibility that—"

"They're coming."

"—the convoy isn't—"

"They're coming, Jack."

Three hours. Four. The sun climbed higher, the wind shifted, and still the horizon remained stubbornly empty.

Finally, a sail appeared—but it wasn't the convoy. It was a small fishing vessel, weathered and listing slightly to one side, crewed by a handful of sun-darkened men who looked more confused than frightened when the Black Pearl pulled alongside them.

"You there!" Barbossa called down. "The merchant convoy out of Kingston—have you seen it?"

The fishermen exchanged glances. One of them, an older man with a face like cracked leather, shook his head.

"No convoy today, Captain. Didn't you hear? Kingston's closed."

Barbossa went very still. "Closed?"

"Aye. Quarantine. Some sickness came in on a ship from the colonies—half the port's down with it. Nothing's coming in or out for at least a fortnight, maybe more."

The silence that followed was deafening.

Jack felt a smile tugging at his lips. He suppressed it. Barely.

"Quarantine," Barbossa repeated flatly.

"Aye. Terrible business. They say the governor himself is bedridden." The fisherman shrugged. "Bad luck for anyone waiting on Kingston cargo, I suppose."

Barbossa dismissed them with a curt wave. The fishing vessel puttered away, leaving the Black Pearl floating alone in the middle of the empty sea.

Jack waited.

Barbossa stood at the helm, his knuckles white on the wheel, staring at nothing.

Jack waited longer.

Finally, unable to contain himself any longer, he spoke.

"So. The mathematics."

"Don't."

"The meticulous calculations."

"Jack."

"The three months of tracking. The precise predictions. The 'creature of habit' who would never deviate from his schedule."

"I am warning you—"

"Did your mathematics account for plague, Hector?" Jack was grinning now, wide and unrepentant. "Did your calculations factor in the possibility of quarantine? Did your careful, methodical, superior approach consider that perhaps—just perhaps—the universe doesn't care about your charts?"

Barbossa turned slowly, and if looks could kill, Jack would have been a smoking crater on the deck.

"There was no way to predict—"

"I predicted it."

"You did not predict a plague!"

"I predicted something would go wrong. I said I had a bad feeling. I said plans go wrong." Jack spread his hands triumphantly. "I was right. You were wrong. Those are the facts of the situation."

"A plague is not a reasonable variable to account for!"

"And yet, here we are. Convoy-less. Treasure-less. Floating in the middle of the ocean because you were so certain your precious plan would work."

Barbossa's jaw was clenched so tight Jack could hear his teeth grinding. "This proves nothing."

"It proves everything. It proves that all your calculations and charts and mathematics mean nothing when the world decides to be unpredictable." Jack sauntered closer, enjoying every moment. "It proves that sometimes—just sometimes—a bad feeling is worth more than three months of meticulous planning."

"We've lost nothing but time—"

"We've lost the element of surprise. The convoy will run a different route once the quarantine lifts—they'll know their schedule was compromised. We've lost fuel, supplies, and crew morale." Jack ticked the items off on his fingers. "We've also lost the very enjoyable experience of watching you be right about something, which I was quite looking forward to."

"You were looking forward to me being right?"

"I was looking forward to you being right so I could graciously acknowledge it and hold it over your head the next time you dismissed my instincts." Jack shrugged. "Now I'll just have to hold this over your head instead. Less satisfying, but I'll manage."

Barbossa closed his eyes, visibly counting to ten. When he opened them again, some of the murderous rage had faded, replaced by weary resignation.

"Fine," he said through gritted teeth. "Your instincts were... not entirely without merit."

"I'm sorry, I didn't quite catch that."

"I said your instincts were not entirely without merit."

"That's not what I heard. What I heard was 'Jack, you were right, and I should have listened to you, and I will never again dismiss your bad feelings as mere paranoia.'"

"That is absolutely not what I said."

"It's what you meant though. Deep down. In your heart."

"I don't have a heart. You know this."

"You have something in there. Spite, probably. But something." Jack clapped him on the shoulder, ignoring the way Barbossa stiffened. "Don't worry, old friend. This happens to everyone. Well, not everyone. Not me, for instance. But most people. Occasionally."

"I am going to throw you overboard."

"You won't. You need me. Who else would be here to point out when your plans go catastrophically wrong?"

"The plans didn't go catastrophically wrong. They were disrupted by an unforeseeable—"

"Plague."

"—circumstance that no reasonable person could have—"

"Plague, Hector. Your plan was defeated by plague."

Barbossa's eye twitched.

Jack's grin widened.

"I'm going to write this down," he said cheerfully. "For posterity. 'The day Hector Barbossa's meticulous plan was undone by a quarantine he failed to predict, despite his superior mathematics and three months of careful tracking.' It'll make excellent reading on cold nights."

"I hate you."

"No, you don't. You're just embarrassed. It's understandable. I'd be embarrassed too, if I'd spent three months planning something only to have it fall apart because I didn't account for—"

"If you say 'plague' one more time—"

"—the inherent unpredictability of human existence. Which, I might add, is exactly what I tried to tell you. Plans go wrong, I said. But did you listen? No. Because Jack's just paranoid. Jack doesn't understand mathematics. Jack—"

Barbossa moved faster than Jack expected. One moment he was standing at the helm, the next he had Jack by the collar, dragging him toward the rail.

"Wait, wait, wait—"

"You wanted to be thrown overboard. I'm accommodating your wishes."

"I very much did not want that—"

"Too late."

Jack hit the water with an undignified splash.

He surfaced, sputtering, to find Barbossa leaning over the rail with an expression of profound satisfaction.

"There," Barbossa called down. "Now we're even."

"We are not even! You were wrong about the convoy!"

"And you're wet. I consider that a fair exchange."

Jack treaded water, glaring up at him. The crew had gathered at the rail, watching with barely concealed amusement. Even Gibbs was smiling.

"You're going to have to let me back on the ship eventually," Jack pointed out.

"Will I? The mathematics suggest otherwise."

"There's no mathematics involved in whether or not you let me drown!"

"There's mathematics involved in everything, Jack. You should know that by now." Barbossa smiled—that sharp, infuriating smile—and turned away from the rail. "Lower a rope. Eventually. After he's had time to reflect on the virtues of gracious victory."

"I was being gracious!"

"You were being insufferable. As usual."

A rope came down—eventually—and Jack climbed back aboard, dripping and indignant. The crew parted around him, wisely avoiding eye contact.

Barbossa had retreated to his cabin, probably to sulk over his charts and pretend the whole thing hadn't happened. Jack stood on the deck, wringing water from his coat, and considered his options.

He could let it go. Accept the dunking as the price of his gloating and move on.

Or he could continue to be insufferable, because that was significantly more entertaining.

He chose the latter.

For the next three days, Jack found every possible opportunity to reference the failed plan.

When Barbossa suggested a heading, Jack would stroke his chin thoughtfully and ask, "Are you sure? Have you accounted for plague?"

When Barbossa consulted his charts, Jack would peer over his shoulder and murmur, "Fascinating. Does this one factor in unexpected quarantines, or is that still a gap in your methodology?"

When Barbossa so much as mentioned the word "mathematics," Jack would nod sagely and say, "Ah yes, mathematics. The discipline that predicted we'd have a cargo hold full of treasure by now."

By the third day, Barbossa had stopped speaking to him entirely.

By the fourth day, he'd started speaking to him again, but only in clipped monosyllables and creative profanity.

By the fifth day, something shifted.

They were in the captain's cabin—their cabin, technically, though the shared space still felt strange after years of solitary command—when Barbossa finally broke.

"Alright," he said, setting down his quill with more force than necessary. "Alright. You've made your point. Repeatedly. With great enthusiasm and very little subtlety."

Jack looked up from the apple he was eating—Barbossa's apple, technically, but possession was nine-tenths of the law. "Have I? I wasn't sure you'd noticed."

"I've noticed. The entire crew has noticed. The fish in the sea have probably noticed." Barbossa rubbed his temples. "What will it take to make you stop?"

"Stop what? I'm simply making observations. Keeping a record of events for future reference. Ensuring that lessons are learned and remembered."

"You're being a petty, gloating child."

"Also that, yes."

Barbossa glared at him. Jack smiled serenely back.

"What do you want, Jack?"

"I want you to admit—genuinely, sincerely, without qualifications or caveats—that I was right and you were wrong."

"I already said your instincts weren't without merit—"

"That's not the same thing. That's you grudgingly acknowledging that I wasn't completely useless while still maintaining your own superiority." Jack leaned forward. "I want you to say, 'Jack, you were right. I was wrong. I should have listened to you.'"

Barbossa's jaw tightened. "That's—"

"Those exact words. In that exact order."

"You can't be serious."

"I'm extremely serious. I've been waiting years for this moment, Hector. Years. You're always so certain you know best, so confident in your plans and your calculations and your superior experience. And this time—this one, beautiful, shining time—you were wrong and I was right, and I want to hear you say it."

The silence stretched between them. Barbossa's expression cycled through irritation, resistance, and something that might have been grudging respect.

Finally, he sighed.

"Jack," he said, the words dragged from him like teeth being pulled. "You were right. I was wrong. I should have listened to you."

Jack's smile could have lit up the entire Caribbean.

"There. Was that so hard?"

"It was excruciating."

"But you feel better now, don't you? Lighter? Like a weight has been lifted?"

"I feel like I need a drink."

"I'll join you." Jack produced a bottle of rum from somewhere—Barbossa had learned long ago not to ask where Jack kept his rum—and poured two glasses. "To learning from our mistakes."

Barbossa accepted the glass, his expression still sour but softening at the edges. "To never speaking of this again."

"Oh, we're definitely going to speak of this again. Regularly. For the rest of our lives."

"I hate you."

"You keep saying that." Jack clinked his glass against Barbossa's. "And yet, here we are. Together. On your ship. That you share with me."

"A decision I question daily."

"And yet you haven't thrown me overboard permanently."

"The night is young."

They drank in something approaching companionable silence. Outside, the Pearl creaked and swayed, carrying them toward whatever disaster would come next.

"For what it's worth," Jack said eventually, "your plan was good. It was solid. It would have worked, if not for—"

"Don't say it."

"—circumstances beyond your control."

Barbossa glanced at him, surprised by the sincerity in his voice. "Are you... being gracious?"

"I'm capable of it. Occasionally. When properly motivated." Jack shrugged. "You're a good strategist, Hector. Better than me, in some ways. But the world isn't a chess board. Sometimes you have to feel your way through, trust your gut, accept that you can't account for everything."

"And sometimes you have to plan, because gut feelings won't tell you where the Navy patrols are or when the tides will turn."

"True." Jack raised his glass. "Perhaps that's why we work. You plan, I improvise. Between the two of us, we might occasionally get something right."

Barbossa considered this. Then, slowly, his lips curved into something that was almost a smile.

"Occasionally," he agreed.

"To occasional success."

"To surviving our own incompetence."

They drank again, and if the atmosphere was warmer than it had been before, neither of them mentioned it.

"Jack," Barbossa said after a moment.

"Yes?"

"If you mention the plague again, I will maroon you on the most inhospitable island I can find."

"Understood." Jack paused. "What about quarantine? Can I mention quarantine?"

"No."

"Unexpected closures?"

"No."

"Disrupted shipping schedules due to unforeseen medical emergencies?"

Barbossa's eye twitched. Jack grinned.

"You're impossible," Barbossa said.

"And yet, you keep me around."

"God knows why."

"Because I'm charming. And occasionally right."

Barbossa shook his head, but he was smiling now—really smiling, that rare expression that softened his weathered face and made him look almost approachable.

"One time," he said. "You were right one time."

"One time is all it takes." Jack settled back in his chair, thoroughly pleased with himself. "One glorious, beautiful, unforgettable time."

"I'm never going to hear the end of this, am I?"

"Not as long as we both live."

Barbossa sighed, the sound of a man accepting his fate.

"Then I suppose I'd better get used to it."

"That's the spirit." Jack raised his glass one final time. "To us. To the Pearl. To plans that fail and instincts that triumph."

"To somehow not killing each other."

"Yet."

"Yet," Barbossa agreed.

They drank, and the Black Pearl sailed on into the night, carrying two captains who would never admit how much they needed each other.

But they knew.

They both knew.