Whitaker was educated at Trinity College, Cambridge and became a clergyman in the North of England.

[1] Travelling to Virginia in 1611, he was a popular religious leader with both settlers and natives, and was responsible for the baptism and conversion of Pocahontas at Henricus two years later.

His relative tolerance of the Native American population that English colonists encountered can be found in his sermons, some of which were sent back to England to help win support for the new colonies in North America.

The most famous of these sermons is Good Newes from Virginia (1613), in which he describes the native population as "servants of sinne and slaves of the divill," but also recognizes them as "sons of Adam," who are "a very understanding generation, quicke of apprehension, suddaine in their despatches, subtile in their dealings, exquisite in their inventions, and industrious in their labour."

[2] Trained as a York merchant, Levett later founded the first settlement at Portland, Maine, where he was granted 6,000 acres (24 km2) by the King.