Pickering apparently had lost his Senate seat to Dashwood, and so viewed him as his arch-enemy. When Dashwood was elected Governor of the proposed State of Malebolgia, Pickering attended the event as an observer, opponent and minor trouble-maker.
Seeing an opportunity to rid himself of a rival, Dashwood helped the demon Marchosias possess Pickering in 2003. The possessed Pickering publicly dropped all opposition to Dashwood's endeavours, including Dashwood's mental institution and the newly reformed Hellfire Club.
Waldo Pickering's granddaughter Becky Lee Kowalczyck lived with him from time to time. She used his home as a local base in her fight against supernatural evil as a member of the Order of Saint Peter. (AUDIO: Minuet in Hell)