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- “Say hello to Big Montgomery, and say good bye to your chances of winning!”
- —Kamek, Yoshi's Woolly World
Big Montgomery appears as the first mid-boss in Yoshi's Woolly World. During his boss fight he uses the background to hide himself. After a short period he jumps out of the background and performs a Ground Pound. When Montgomery does this attack, Yoshi needs to shoot him with a yarn ball as soon as possible to damage him. Big Montgomery later reappears as the mid-boss of World 3 and World 5.
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