[2] The Forest of Dean contained rich deposits of iron ore and, with charcoal made from its timber, had been the location of ironworks back to Roman times.
In 1624 it was claimed that Winter "and other Papists" were storing gunpowder and ammunition at his uncle's fortress, Raglan Castle and were plotting rebellion against King James.
[3] He obtained a 21-year lease from the Crown for forty thousand cords of wood in 1628, but had to give this up in 1634 when a forest eyre found that he had exceeded his rights.
[4] On 20 February 1640, Sir John paid £10,000 for all the mines, minerals, and stone-quarries in the Forest of Dean, together with rights to all the timber, trees, woods and underwood growing there.
Sir John Corbet, in his contemporary account, An Historical Relation of the Military Government of Gloucester, said that Winter was "wise for himselfe, nimble in inferiour business and delighted more in petty and cunning contrivance than open gallantry..." In October 1644, he joined with Prince Rupert to attempt to re-occupy the crossing point of the River Severn at Beachley which had been taken by Massey's Parliamentarians.