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Guide: To play Oswald like a pro, you have to start out with a good damage item. Always keep building damage items in order to get money from your teammates. Always find a way to get your allies murdered. Go out there and find ways to make the game very hard on your team. If you want to go very pro with him, build 6 trinity forces on Oswald and play him jungle, for sure you'll win.
DONT READ LORE IF TL;DR
LORE: Once upon a time, Oswald was an annoying obese college student, then that all suddenly changed when he was accidentally summoned onto summoner's rift. The summoner who accidentally summoned him was probably that midOrAFK guy in your last game. During that time Oswald was on his camping trip, so he had his fishing pole, hatchet, and money in his pocket that kept growing. When Oswald was beemed down, the champions around him were flabbergasted at the sight of an ordinary man. But news started spreading around the League when Oswald turned out to be a very destructive champion. All the trolls started to abuse him non-stop and this became so bad that the high council of The League of Legends couldn't kick him out because of too many technical difficulties. From that day forward, Oswald is now a hated enemy of all the League and Champions. The only ones who really liked him were Trundle, Brolaf, Blitzcrank, Alistar, and Thresh
Passive
And you thought I Was on Your Side: Oswald can preform auto-attacks on his own allies but he'll only deal half damage to them. His own turrets won't attack him nor the spawn fountain.
Q
Wait I Gotta Tell You Something: Oswald throws out his fishing pole and casts his line out in a 750 long skill shot. Whatever the lure hits first, he'll reel in an allied/enemy champion towards him. This also works on non-legendary minions.
W
IT'S MINE LET ME HAVE IT: Oswald's next basic attack causes him to strike an enemy based on their missing health. If he presses the ability the second time costing him extra mana, he'll toss his hatchet out which has 500 distance.
E
Man Full of Gold: PASSIVE - The value of Oswald's bounty increases by 10 gold everytime he gets killed. He cannot decrease his own bounty.
R
You Go Ahead, I'll Stay Here/Hide Under Me, you'll be safe, trust me: Oswald picks up an ally champion within 150 distance of him. He can cast his ultimate again to toss his ally in a straight skill shot from 0 to 800 distance. If he does nothing for the 5 seconds after the first cast, he'll throw his ally under him and sit on him/her for 10 seconds. Both Oswald and his ally are targetable during the sitting.