This particular phrase quest started with the Regency slang expression ‘in the basket’, which in general means empty-pocketed, unable to pay one’s debts.
According to Mr. Partridge’s Dictionary of Slang and Unconventional English:
‘Basket!’ – a cry directed, in cock-pits, at persons unable to unwilling to pay their debts: C. 18. Such persons were suspended in a basket over the cock-pits. Hence basketed, left out in the cold, nonplussed: late C. 18-19.’ ‘Basket, be brought/go, to the – to be imprisoned: C. 17-18 coll.’
And then I got sidetracked.
(‘Sidetrack: to move from the main track to a siding, as a train; to move or distract from the main subject of course. This stuff is addictive.)
‘Going to hell in a handbasket/handcart’ – meaning deteriorating rapidly, being on a course for disaster — seems to be one of those phrases that gives rise to considerable speculation but has no firm foundation in historical fact. It’s cited in the Oxford Dictionary of Proverbs as being from a 1626 sermon which equates ‘go to heaven in a wheelbarrow’ with ‘go to hell in a handcart’.
Eric Partridge, in his Dictionary of Catchphrases, dates the term to the early 1920’s.
The Oxford English Dictionary cites its first use in a historical work of 1876.
The most colorful – and ghoulish – theory has to do with the French Revolution and Mme Guillotine and the basket that was used to catch the severed heads. (Apparently those poor souls who were beheaded were destined straight for hell.) ‘Head in a handbasket’ is a phrase dating at the least to Samuel Sewall’s Diary, 1714.
The least common theory has to do with the building of the transcontinental railroad in mid-19th century America. Chinese laborers were placed in wicker chairs and suspended over cliffs with ropes. The laborers would bore into the rock and insert dynamite charges and light the fuses. Depending on the strength and speed of the men pulling the ropes, the laborers made it safely to the top or alternately were blown—Yep. To hell in a handbasket.
Whatever may be the case, (and I really like this), the medieval stained glass windows of Fairford Church in Gloucester contain an image of a woman being carted off to purgatory in a wheelbarrow pushed by a blue devil, so the idea itself has been around almost five hundred years.
Back to Mr. Partridge’s Dictionary:
A basket-scrambler is one who lives on charity: C. 17-18.
And a basket of oranges is a pretty woman, as of late c. 19-early 20.