Kingston was a feisty individual and no stranger to involuntary confinement. Born in 1822 in Guyana (though with English heritage as well), he joined the HBC in October of 1846, and sailed to the Pacific on board the Cowlitz. He fought with many on his voyage, and was forced into irons.
He was an opinionated man and often argued with his superiors. He fought Captain James Sangster of the Cadboro to serve men their main meal at lunchtime rather than after work. Before his time in Fort Victoria, he spent about a month off-duty due to eye problems, which may have influenced his unruly behaviour. After an incident with a native man at the fort, he was forced back on the Cadboro in irons, as he had refused to go to Fort Nisqually. He was back in Fort Victoria in 1851, this time serving a prison sentence in the lower floor of the bastion. Kingston was let out to help lay the sidewalk stones for Fort Street.