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3.
1.) A place where Jon Jon can't swim!

2.) An island where the Kennedy's lived.

3.) Motto made famous by the Mayor of Springfield.

4.) Ridiculous; stupid.

5.) Yelled in rage or frustration
I want to go to Chappaquiddick and see the Kennedy's house!

CHAPPAQUIDDICK! Jon Jon can't swim!

THATS FUCKING CHAPPAQUIDDICK!

Stop being so Chappaquiddick Agnes, you look like a durn fool!
by iThizz July 01, 2006
 
1.
The Chappaquiddick incident refers to the circumstances surrounding the 1969 death of Mary Jo Kopechne, a former staff member in Senator Robert F. Kennedy's 1968 presidential campaign. Edward Kennedy was driving a car with Kopechne as his passenger when the Senator drove off Dike Bridge into the channel between Chappaquiddick Island and Martha's Vineyard. The Senator swam to safety, but Kopechne died in the car. Kennedy left the scene and did not call authorities until after Kopechne's body was discovered the following day. He pleaded guilty to leaving the scene of an accident and was sentenced to two months in jail, suspended.

Chappaquiddick Island is a small island off the eastern end of the larger island of Martha's Vineyard and is part of the town of Edgartown, Massachusetts
by Trentwood22 July 22, 2008
 
2.
A better word than cool, swell, awesome, rad, or even lovely. Not quite as good as clever because clever is clever. All the same, we do our best.
Baby, the way you groove my knob without complaint is just so chappaquiddick.
by eamander December 04, 2010