Estranged from his affluent family and floundering in his early career choices, Anglophile Charles Elliott Sturgeon has an improbable dream. Having perfected a winning strategy at blackjack, his goal is to compete and defeat the world's foremost cardsharp, Lord Bruce Huxley Evanston– that while also wooing his female British pen friend who he has never actually met in person.

In this witty and nostalgic "fish-out-of-water" tale of self-discovery, the naïve young American travels to post British invasion England in the hopes of achieving his driving ambition. Fate, however, may have other plans. While establishing his card-savvy reputation and inching closer to realizing his prime objective, Sturgeon learns some harsh, unexpected lessons along the way – and ultimately the true meaning of "winning."