Career
Jack was one of the richest and most influential English cloth merchants of the early 16th century. As the nickname suggests, he resided in Newbury in Berkshire. The name is often mistakenly attributed to John Smallwood, alias John Winchcombe (1465 - 1519).
This was John Winchcombe II's father, a man who originally came from Barking in Essex. Jack was supposedly born in Newbury in Berkshire under the name John Winchcombe. His father, John Smallwood alias Winchcombe (1465 - 1519), traveled from Barking in Essex to Newbury around 1500 as a clothier.
Over the course of his life, he is said to have set up the first factory in England, sent troops to the battle of Flodden, and refused a knighthood from King Henry VIII. His story is told by Thomas Deloney in his Pleasant History of John Winchcombe and less fully in Thomas Fuller's History of the Worthies of England. Jack was a great patron of Newbury and the site of his house can still be seen off Northbrook Street. Contemporary panelling from this building can be seen in West Berkshire Museum.
His father began the rebuilding of St. Nicolas Church in 1500 and was buried there under an extant brass memorial upon his death in February 1519. Jack invested in the Church as well, but also became a MP.