Winstone had a somewhat tempestuous personal life at times. In September 1959 he obtained a court order that banned his mother-in-law from staying at his home. In the same month a court ordered that an "iron curtain" be constructed in the property so as to split the rooms between himself, then aged 46, and his wife and two-year-old daughter. He was also ordered to stop playing his piano by 6pm each day in order not to disturb his family. At that time he was using it to compose arrangements for three bands and five radio shows.