Wrestling Brewster was born in Leiden, Holland, to parents William and Mary Brewster. His father William was the Elder of the congregation, and in Leiden was a teacher of English and also published books on religion and theology (most of which were illegally sent into England).
At the age of about 6, he came with his father and mother on the Mayflower to Plymouth. He was alive during the 1627 Division of Cattle at Plymouth, where he is listed in the household of his father William. He is not mentioned again in any other record.