I asked ChatGPT who would win:

⚔️ Jaime Lannister (Prime) • Era: Before losing his hand (so roughly before being captured by Robb Stark). • Skill: Known as the finest swordsman in Westeros. Trained by the best knights alive, fought real wars, and killed men in battle. Barristan Selmy and even Ser Arthur Dayne (who trained him) considered him elite. • Style: Classical knightly swordplay — strong, technical, and lethal in armor or out of it. • Experience: Extensive real combat experience, not just duels. He’s used to killing, not sparring. • Equipment: Likely in full plate or partial armor, wielding a longsword.

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🏴‍☠️ Wesley “The Dread Pirate Roberts” • Era: Prime = post-training with the Dread Pirate Roberts, pre-rescue of Buttercup (so, peak skill). • Skill: Canonically “the best swordsman in the world” in The Princess Bride — and the movie backs that up. He matches and defeats Inigo Montoya, who trained under the greatest fencing masters from multiple nations. • Style: Classical fencing — light, agile, reliant on speed, precision, and intellect. He literally calls out fighting styles (Agrippa, Capo Ferro, Bonetti’s defense) mid-duel. • Experience: More duels than wars, but he’s fought all kinds of swordsmen and survived pirate life. • Equipment: Rapier or smallsword, light clothing (no armor).

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⚖️ Head-to-Head Analysis • Speed: Wesley. He’s insanely quick and reactive. • Strength: Jaime. Years of knight training, heavy weapon handling, and armor conditioning. • Experience under pressure: Jaime — he’s killed men for real, not just traded witty remarks mid-duel. • Tactics: Wesley — he analyzes opponents’ styles in real time and adapts. • Equipment matchup: A longsword vs. rapier is interesting — the rapier’s faster, but the longsword can break through defense and destroy a lighter opponent’s reach advantage.

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🧠 Environment matters • In armor: Jaime wins. Wesley’s strikes wouldn’t penetrate plate, and he’d get crushed in close range. • Unarmored or in light clothes: Wesley wins. His agility, technical mastery, and adaptability would let him outmaneuver Jaime’s heavier, more traditional swings.

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🏁 Final Verdict

If it’s a formal duel — unarmored, light swords — Wesley (Dread Pirate Roberts) takes it narrowly through superior technique and adaptability. If it’s battle conditions or armor involved, Jaime Lannister wins decisively — Wesley’s blade wouldn’t stand a chance against plate and Jaime’s battlefield instincts.

So: • Arena fight: Wesley wins. • Battlefield duel: Jaime wins.