Jacob along with his brother Simon Waligh (b. unknown d. 3//1649) were the first of the Van Winkle family to arrive in America from the Netherlands in 1630.
The brothers were given parcels of land to farm from the Kiliaen van Rensselaer estate which included Papscanee Island.
Jacob became a member of Council of twelve men which was the first representative official body within the states of New York, New Jersey, and Connecticut.
After unsuccessfully trying to start a community along the Connecticut River and drive out the encroaching English settlers, Jacob settled down to farm a large parcel of land located in Pavonia.
A particularly severe out break of hostilities between the natives and the colonists known as the Peach War forced survivors, including Jacob, to flee to Fort Amsterdam on Manhattan Island.