The Phrase Finder defines the expression means “…to be rapidly deteriorating—on course for disaster.” It goes on to say that it isn’t all that clear why a handbasket is preferred to transport people to hell, although there is a theory that it comes from baskets being used to catch heads removed by the guillotine. An alternate expression is going to hell in a handcart. A medieval stained glass church window shows a woman being taken to purgatory in a wheelbarrow pushed by a blue devil.