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Before Lakitu informs Yoshi of the events transpiring in Princess Peach's Castle, Chief Chilly, along with Bowser, Goomboss, and King Boo, ambush Mario, Luigi, and Wario, the latter being put under Chief Chilly's protection. However, when speaking to a challenger, he claims that he locked Wario up simply because the brute challenged the superiority of his mustache. Luigi comes to Wario's rescue and is forced to battle the monstrosity. Despite being the weakest of the three mustached heroes, he manages to beat the boss and push Chief Chilly off of his iceberg three times, giving Luigi the key to Wario's prison. Chief Chilly disappears after the battle to restyle his mustache and to vow revenge. During his first battle, it gets tricky, as every time he is pushed in the water, he knocks off portions upon returning, making it smaller. After taking a second hit, he rocks the iceberg and, when pushed to the edge, maintains his balance for a little before going back to the middle. It is best for Luigi to smash him while he was slipping, In other cases, Mario could also defeat Chief Chilly if the player picks up a Mario cap in the level.

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