His career as a missionary made him "a well-known figure, universally respected",[1] in particular his interventions and friendship with the notorious Jane Cakebread.
From the age of twelve until he was thirty-three, he was an iron-moulder like his father; a serious accident in 1877 forced him to find a less physical job.
[2] Police-court missionaries were the fore-runner to probation officers, as their initial function was to "reclaim drunkards" and subsequently other offenders too.
This developed into a system of releasing offenders on the condition that they would stay in touch with the missionary and accept their guidance.
Holmes worked as a missionary for twenty years, and dealt with thieves, drunkards, prostitutes, and other criminals.
[7] Jane Cakebread (1827/1828 – 17 December 1898) was a homeless woman notorious for her frequent arrests for public drunkenness; she appeared in court 277 times, and is credited for inspiring the Inebriates Act 1898.
Holmes staged many interventions for her, providing her with clothes and money for accommodation, and she would frequently attempt to go see him whenever she was discharged from prison.
[8] Cakebread told Holmes he could inherit her (non-existent) fortune, and once proposed to him;[9] her prized possessions were the clothes he gave her.
He worked there for ten years and provided advice to successive Home Secretaries on prison reform.
[2] In 1910 he set up Singholm, a guest house in Walton-on-the-Naze, where forty women at a time could relax during their fortnight's holiday.