Charles Henry Pope's "Pioneers of Massachusetts" says this:
WILLARD
Simon, Cambridge, propr, 1634. Removed to Concord, Sergeant; appointed to
exercise the military company 13 (8) 1636. "A Kentish soldier;" Was
either deputy or Assistant for about 40 years. Major. Had a patent, with
associates, in 1641, for trading with the Indians and collecting tribute from
them. Removed to Lancaster. Signature in inv. of Thomas Atkinson in 1646. A man
of unusual energy, sagacity and character.