It means that everyone immediately thought Will was stupid.
It's a colloquium that refers to this baby toy, with wooden pegs or blocks. Each peg is cut into a different shape: square, circle, triangle, and more. There is also a board with the same shapes cut into it. Each peg only fits into the hole with the same shape. So the baby has to stick the right pegs into the right holes. It teaches babies to recognize and sort shapes.
So in the example willed being "pegged" as stupid means everyone realized that will was the "stupid" shaped peg and fits in the "stupid" hole (category)
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