No one seems to know where the phrase, "going to hell in a handbasket" came from. I'm pretty sure based on history that those "criminals" who were beheaded in England and had their heads then displayed on London Bridge until they were picked clean by birds and weather, had those heads carried there in a basket from the scene of the beheading.
Since no one would have disputed aloud that these were not criminals, it was assumed they were going to hell.
I don't consider Thomas Cromwell a criminal or Anne Boleyn, but Henry VIII sure did. He transformed lots of his helpers into "criminals" and, with his unlimited power, had them beheaded.
So, if you are going to hell in a handbasket, you are someone who is messing up their lives so badly that you are looking forward to capital punishment, and then a quick trip to hell for eternity. To sum up? Not good.