Robert Lenton was born somewhere between 1808 and 1818 in Gretton, Northamptonshire in the midst of the industrial revolution. Gretton was predominantly an agricultural area with a history dating back to the Iron Age, but with the advent of industrialisation the requirement for labour was greatly lessened and the once productive farm workers had to seek alternative work or starve.  The residents of Gretton had a typical rural life wrestling with hunger, poverty and disease, political, social and environmental changes.  One upheaval which particularly affected them was the Enclosure Act when common land was enclosed and the local farmers could no longer graze their animals or grow their produce there.

This was about this time that Robert commenced his life of crime, starting with a bit of poaching, some petty stealing and ending with the theft of a pair of wellington boots. It would seem that Robert, like many others, had turned to stealing as an alternative to starving.  They had little choice; they stole to survive and to help their families survive. These were harsh times and opportunities were scarce.

He was wearing the said stolen boots when he was apprehended.  Convicting Robert was not difficult for the authorities as he and his partner-in-crime were already incarcerated at Oakham Gaol for another offence.  Theft of wearing apparel was more commonly linked with female convicts, but Robert was twice charged with stealing other people’s boots; the second conviction resulting in his transportation to Van Diemen’s Land.  The women would steal items such as gloves, shawls or handkerchiefs which they would sell, but Robert stole boots to wear.