Samuel Winter (Usher 1626-1627, Headmaster 1627-1630)

We find the following statements in connexion with the life of Mr Cotton - Samuel Winter, DD, afterwards Provost of Trinity College, Dublin; after he left Cambridge, went to Boston in Lincolnshire, where he lived under the ministry of the learned John Cotton; out of whose family, after some time, he married Mrs Anne Beeston (Bestoe), a gentlewoman of good extraction, and one that had a considerable portion; the match being one of Mr Cotton's contrivance. After his marriage, and some continuance with his wife, in Mr Cotton's family, he applied himself to the work of the ministry, and removed to a small living in Woodbarrow, near Nottingham, and from there to Cottingham, near Hull, where his wife died, leaving him with five sons. He then married Mrs Elizabeth Weaver, and, in 1650, he went to Ireland; he died at South la Henham (?), in the county of Rutland, Dec 29, 1666 - Middleton's Biog Evangelica, vol iii, p 395.

From The History and Antiquities of Boston by Pishey Thompson

Watson left [as headmaster of Boston Grammar School] in 1627 for clerical appointments, first as vicar of Horbling, then as rector of Aswarby, and was succeeded by Samuel Winter, the school's usher and a Cotton protégé.

George Atkinson replaced Winter in 1631 after Alderman Westland had ridden into Yorkshire and to Cambridge, and Thomas Coney to Lincoln, about the vacancy.

From Boston, its Story and People by Geo. S Bagley