Water in the boat is always on the wrong side - the added weight shifts to the lower downwind side and pulls the boat further towards the water. If the boat tips enough, the river rushes in and pulls the boat into a capsize.
The Charles River basin is surprisingly shallow; a boat turned completely upside down, or “turtled,” will get the top of its mast stuck in the mud at the bottom and become very difficult to right. Thus it's important to right the boat quickly before the mast digs in.
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