John Cheswas was born at Newcastle-under-Lyme but spent the bulk of his life at the Cheshire village of Prestbury. Variously referred to as both ‘Jack’ and ‘Johnny’, he rode with a fair degree of success from the 1820s to the late 1850s and remained actively involved in racing until his death.
In 1827, he was awarded one farthing at the Stafford assizes against the printer of the Wolverhampton Chronicle for a libel, imputing that he, the plaintiff, had deliberately lost a race on Arachne at Stourbridge.
He died at Prestbury on December 16, 1869. He was said to be 65, although that may not be entirely accurate.
His obituary in Bell’s Life described him as being an “eccentric” character. The paper doesn’t elaborate on that, other than noting that he was the subject of many jokes but “respected” nevertheless. It may be that he had idiosyncrasies with regard to his style of riding, though that can only be conjectured.