It is 1934. Red-headed Henry Cook, fresh out of Amherst and excited about working on his first book at an infamous writers' colony, arrives at the Vermont island retreat at the invitation of its owner, Thaddeus Hulbert, a boisterous, bellowing, bloviated curmudgeon, whose reputation as a novelist, columnist, and radio commentator has vaulted him to national prominence.

Additional island guests include Clarence Fitch, the editor of a prominent New York magazine; Agnes Sterner, an elegant, mature woman, also an author and close friend of Hulbert's; Daisy Lester, a nationally-known nightclub singer also known by Hulbert and friends to be a heavy drinker if not watched carefully; and Leith O'Fallon, an artist, writer, and liberal cause protester for whom Henry falls hard.

Among the supporting characters are Mr. Veitch, the slow-drawling Vermonter who navigates the mail boat to and from the island, and Jenny, the shrieking housekeeper and cook who tends - genially if not loudly - to the needs of Hulbert's guests.

Entirely Surrounded is a slightly venomous roman à clef poking satirically at the habits of several of the Algonquin Round Table notables: Alexander Woollcott (Hulbert), Alice Duer Miller (Sterner), Dorothy Parker (Lester), Harold Ross of the New Yorker (Fitch), and Neysa McMein, popular magazine cover illustrator (O'Fallon). The novel's author and narrator, Charles Brackett (Cook), had been a regular at the Algonquin for several years before leaving for Hollywood at the peak of the group's notoriety. Through Entirely Surrounded, Brackett deconstructs the Round Table's core elite and re-assembles them on their lake encircled hideaway to endure each other's company, play croquet, backgammon, cribbage, and anagrams, all under the withering snide and cutting bombasts of their host, Hulbert.

The story's narrator, Henry Cook, is the mean gang's naïve foil, surrounded as he is by the idols of his literary dreams, viper-toothed gods who pick petty fights over silly games, and chide each other, and Henry, mercilessly over points of literature and social graces. And yet, there is compassion and love to be found on the island, and a twist to the tale that brings Henry face-to-face with his deepest insecurities. Brackett, one of the earliest New Yorker drama critics, prolific magazine columnist, and short-story author and novelist, brings to Entirely Surrounded elements of his own New England upbringing, his Ivy League education, his curious marriage, and his not-well-concealed need for social and professional approval. Brackett knew all the players quite well, and though the book is a biting commentary on the group's interrelationships and foibles, Brackett received grudging congratulations even from Woollcott and Parker, who took the majority of Brackett's jabs.

Entirely Surrounded is narrated by Charles Brackett's grandson, C. James Moore.