Waite's Gamble: A Revolutionary Legacy In 1782, settler William Waite risked everything — purchasing 450 acres of Cambridge land before the Revolution's outcome was secured. Had Britain won, his investment would have been worthless overnight. He bet on freedom. He won. South Dominion Vineyard stands on that very land today. Our fortified wine, Waite's Gamble, honors his courage — one sip, two centuries of history. Come taste the story.