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Jack O'Newbury was indeed a rich clothier who lived in the town after which he was named. Though a great benefactor to the town, little is known for certain about him. It is assumed that much of his legendary background is true, however, for it was written down only seventy years after Jack's death, by one Thomas Deloney in his "Pleasant History of John Winchcombe". He expands our "Dick Whittington" tale of rags to riches to cover the whole of Jack's life, but more of that another time.

As our story reveals, Jack's real name was John Smallwood. He is believed to have been born in the town of Winchcombe in Gloucestershire as this was the surname he took on arriving in Newbury. His descendants, the Winchcombes of Bucklebury, used the name until the line died out in the late eighteenth century. Jack's trade apparently specialised in a type of cloth known as kerseys, much of which he exported to the fairs in Antwerp. He is recorded as having had 160 looms in his house, each of which was worked by one man and one boy. This does indeed merit him with the distinction of being the man to have set up the first true factory in England.

Jack's wealth probably did stem from an advantageous marriage. His wife, Alice, is well documented, but whether it was really her conniving that won him over or vice-versa we shall never really know. Unfortunately, parish registers began some time after their marriage, but the chapel attached to St. Bartholomew's Hospital was certainly in existence then. The hospital was probably founded by King John in about 1210. The present chapel, called the Litten, is not quite that old but does date from the 15th century, so would have been the same building in which Jack was married. It is interesting to note, however, that to reach St. Bartholomew's the two would have had to pass the parish church of St. Nicholas which, in later life, Jack had totally restored. Why did they not marry here?

Jack died in 1519 and was buried in St. Nicholas' Church where his memorial brass still survives.

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