Principal Peskin's sailboat turns up in the school swimming pool with the words 'Class of 2001' emblazoned on the sail in white paint. On board the boat is his dog, Chester, who was kidnapped the previous day. Dawson, Pacey and Jack are all prime suspects in the prank. Pacey is the only senior with access to the boatyard from where Peskin's boat was stolen, Dawson has keyholder access to the school through his father's job (and therefore would have the ability to get the boat into the pool after hours), and a nervous Jack attracts attention from Chester, as well as admitting to buying white paint. After their interrogations reveal seemingly air-tight alibis, another culprit surfaces and some poetic justice is dished out.