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Frank Castle from Punisher: War Zone.

VS

Bucky from Captain America 2.

Round 1: They fights against each other with weapons in Time Square NYC.
Weapons: Frank has a KA-BAR, AR500 Body Armor, Smith & Wesson M500 with 60 rounds, two H&K MP5K with 300 rounds and a Full Auto supressed AR-15 Carbine w/H&K AG36 Grenade Launcher loaded with 150 rounds and 2 40mm grenades.
Bucky has his knives he used in the movie, SIG-Sauer P220ST with 100 rounds, Vz.61 Skorpion with 300 rounds and a M4A1 w/M203 loaded with 150 rounds and 2 40mm grenades.
Range: They starts against each other from 70m.

Round 2: H2H inside Helicarrier. Frank got a pair of Brass Knuckles and Bucky has his robotic arm.

Who wins and why?

Round 1 goes to Punisher. That dude was an absolute beast with his targeting and weapon use. I'd give him a pretty big edge here over WS

Round 2 goes to Bucky pretty easily. This is a dude who fought on even ground with Cap