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Grand Strategist's Gamble

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Synopsis
They gave him a broken fiefdom and a death sentence. He'll give them an empire in return. When Kaito Tanaka, a military strategist deemed too ruthless for the modern world, wakes up as Kaelan von Greyrat, he knows he's been handed the worst deal imaginable. His new family despises him, his soldiers mock him, and a barbarian horde is weeks away from slaughtering them all. But Kaelan has a secret weapon: a System that rewards brilliant tactics with unimaginable power. While knights prepare for a glorious last stand, Kaelan plays a different game. He fights with blackmail instead of blades, with economics instead of armies. Every humiliation becomes a strategic advantage. Every "coward's move" makes him stronger. Soon, the nobles who laughed at him will beg for mercy, the barbarians who sought to crush him will flee in terror, and the kingdom that abandoned him will kneel at his feet. But Kaelan's rise attracts attention from powerful forces beyond his understanding. Other players in this deadly game have been transported to his world, each with their own terrifying abilities. To survive, Kaelan must uncover the truth behind his transmigration and face an enemy who knows all his tricks, because they play the same game. He was given nothing. He'll take everything.
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Chapter 1 - A Strategist's End, A System's Beginning

The last thing Kaito Tanaka knew was the blinding glare of oncoming headlights and the sickening crunch of metal. There was no pain, just a sudden, violent ending. His final, bitter thought echoed in the void. The strategy was sound. They were just too weak-willed to see it through. Too afraid of "unconventional" methods.

He had been one of the Pentagon's most promising strategic analysts, a mind capable of modeling global conflicts with terrifying accuracy. And they had fired him for it. Now, he was nothing.

But then, he was something again.

Awareness returned in a torrent of unfamiliar sensations. The rough texture of a wool blanket. The pungent smell of woodsmoke and unwashed bodies. A dull, throbbing pain in his cheek.

"—cowering in your room while real men defend your walls, you useless worm!" a voice roared, thick with contempt.

Kaito's eyes snapped open. He was lying on a simple bunk in a stone-walled room. A giant of a man, clad in worn leather and steel, was standing over him, his hand still raised from the slap he'd just delivered. The man had a brutal, honest face, contorted with fury.

This wasn't his body. These weren't his memories, but they flooded him anyway, a chaotic stream of information.

His name was Kaelan. Kaelan von Greyrat. Third son of Baron von Greyrat. They were on the frontier, in a place called the Northpass. And he was known to all as "Kaelan the Coward."

The giant, his brother Roderick, grabbed the front of his tunic. "Did you hear me? Goblins! A scouting party is at the gate, and you're hiding like a frightened child!"

Goblins? Kaito's—no, Kaelan's—mind, still reeling, instinctively latched onto the tactical problem. It was a familiar anchor in the sea of madness. Scouting party. Probing defenses. Standard procedure for a weaker force.

"Where... how many?" Kaelan's voice was a rasp, unfamiliar to his own ears.

Roderick blinked, startled by the question, then sneered. "What does it matter to you? Five of the filth, and a shaman. They're taunting us from the tree line by the south gate."

A shaman. That implied magic. A potential force multiplier. The five warriors were a distraction. The real threat was the spellcaster.

As he thought this, something impossible happened. A flickering, transparent blue screen materialized at the edge of his vision. The text was crisp, unfamiliar, yet he understood it perfectly.

[Threat Analyzed: Goblin Scout Party.]

[Composition: 5 Warriors (Tier 0), 1 Shaman (Tier 1).]

[Optimal Strategy Calculated: Feigned retreat from south gate, draw warriors into chokepoint at the old stables. Neutralize shaman with projectile focus. Estimated Success Rate: 92%.]

Kaelan stared, his breath catching in his throat. Was this a hallucination? A dying dream? The System, as he instinctively knew to call it, remained, patiently waiting.

"Roderick, listen to me," Kaelan said, his voice gaining a sliver of strength. He pushed himself up, ignoring his brother's look of utter shock. The old Kaelan would have been sobbing by now. "The shaman is the key. They're trying to lure your knights out. The trees provide them cover."

"Of course they have cover! That's why we charge them and break their line!" Roderick roared.

"No. You'll be hit by a hex or a curse the moment you're bunched up in the open," Kaelan countered, his mind racing, the System's analysis merging with his own expertise. "Order a feigned retreat from the south gate. Let them think they've scared us. They'll get overconfident and chase straight into the narrow path between the stable and the warehouse. It's a natural kill zone."

Roderick stared at him as if he'd grown a second head. "A... feigned retreat? That's... coward's tactics! We are Knights of Northpass! We do not retreat!"

"It's not a retreat; it's a tactical repositioning!" Kaelan snapped, a flash of his old authority, the authority of a man who had briefed four-star generals, cutting through his voice. "Once they're in the chokepoint, your archers on the stable roof can focus fire on the shaman. The rest can pick off the warriors who are trapped. Zero risk to your men. Total annihilation of the enemy."

The words hung in the air. Roderick's fury was now mixed with profound confusion. This was not his brother. The plan was... heretical. And yet, it was chillingly logical. He could see it in his mind's eye. The goblins, thinking victory was theirs, rushing headlong into a trap.

A horn blast echoed from the courtyard below, sharp and urgent. The sound of clashing steel and guttural war cries followed. They were out of time.

"Fine!" Roderick spat, making a decision born of desperation rather than trust. "By the name of the King, if this fails, I'll throw you to the goblins myself!"

He turned and stormed out of the room, bellowing orders to the men below. "Archers, to the stable roof! South gate, fall back! Draw them in! Now!"

Kaelan stumbled to the small, arrow-slit window, his heart hammering against his ribs. He watched the scene unfold below. A handful of his father's men-at-arms, who had been holding the gate, suddenly turned and ran, acting panicked. As predicted, the five goblin warriors, seeing the retreat, let out triumphant screeches and gave chase, their scrawny forms darting forward. The shaman, a taller figure adorned with bones and feathers, followed at a more cautious distance, its hands already weaving a faint, sickly green light.

They poured into the narrow alley between the stone stable and the wooden warehouse.

"Now!" Roderick's voice boomed.

From the stable roof, a volley of arrows whistled down. They were not aimed at the warriors. Every single one flew towards the shaman. The creature looked up, its red eyes wide with surprise, and raised a hand. A shimmering barrier of energy deflected the first two arrows, but the third and fourth found their mark, sinking into its shoulder and thigh. The green light around its hands sputtered and died.

The goblin warriors, now realizing the trap, tried to turn back, but they were packed too tightly in the narrow space. The men-at-arms who had feigned retreat now turned, their faces grim and determined, and attacked from the front, while other soldiers closed off the rear. It was a slaughter. In less than a minute, it was over. 5 goblin bodies lay still on the muddy ground. Not a single human had been seriously injured.

A ragged cheer went up from the defenders.

Kaelan let out a breath he didn't know he was holding. It had worked. The 92% probability had played out. He leaned his forehead against the cool stone, the adrenaline crash making him tremble.

Then, the blue screen reappeared, brighter and more solid than before.

[Battle Conclusion: Overwhelming Victory.]

[Forces: 12 vs. 6. Casualties: 0 vs. 6.]

[Gambit Multiplier Activated: 2.0 (Inferior Force - Perceived).]

[Insight Points Gained: 10 IP.]

Insight Points? A Gamble Multiplier? Before he could even begin to process this, a new, more urgent screen flashed, its text a stark, warning red.

[Critical Alert: Liege Lord's Vital Signs Critical.]

[Baron Siegfried von Greyrat has succumbed to his wounds.]

[Status: Deceased.]

The message hung in the air, cold and absolute. The victory against the goblins was meaningless. The Baron was dead. The leadership of this crumbling, doomed fief, and the fate of everyone in it, had just fallen onto the shoulders of his two glory-seeking older brothers.

And the System had just shown Kaelan the first, terrifying glimpse of the true war to come.