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.