On Canaan’s Side is a 2011 novel by Irish author Sebastian Barry. It’s a first-person narrative by 89-year old Lilly Bere, telling her life story in a series of journal entries. Using Lilly’s experience as an immigrant to the United States, the tropes of a thriller novel, and an extended sense of suspense as to Lilly’s ultimate goals, the novel turns Lilly’s life into a wide-ranging commentary on the Irish diaspora and America’s influence on the people who emigrate there.
The novel opens with Lilly announcing that Bill, her grandson, is gone. She then remembers the heartbreak she experienced as a little girl when a prized doll given to her by her aunt is dropped and shatters. She has other memories—of her father telling her about being born, of having her own child in Cleveland, of life back in Ireland. Then she announces she will start properly. She reflects that one of her good friends, Mr. Nolan, recently died, and that since deaths come in threes she assumes her own will be next. She says she will end her life shortly, because she cannot live without Bill. She does not think it proper to end her life without explanation, however, and she has no suitable audience, so she decides to write down her explanation in a journal. Each chapter of the book is a daily journal entry spanning seventeen days after Bill’s funeral.
Her neighbor and friend, Mr. Dillinger, who has been leaving her flowers after Bill’s suicide, visits. He becomes awkward, unable to console her, and so leaves, and Lilly recalls an earlier time when Mr. Dillinger gave her a book as their friendship was just beginning, which leads her to recall her childhood in Ireland. Her father was a policeman employed by the British at the time, just before World War I, when rebellion was in the air and the IRA hated and attacked anyone seen to be colluding with the British. He is appointed Chief Superintendent and the family moves into Dublin Castle, which Lilly finds grand. Her father’s enemies, Irish rebels, release a circus bear into the family’s quarters on their first day in an attempt to intimidate him.
Lilly is engaged to Tadg Bere, who fought in the Great War for the British as well, and he is also regarded as a traitor and attacked by the IRA. Tadg becomes one of the infamous Black and Tans, a special police force organized specifically to put down the Irish rebellion.
Tadg and other Black and Tan members are ambushed, and several Irish rebels are killed. Soon Tadg has a price on his head, and he and Lilly flee to America. They arrive in New York and make their way to Chicago, which Lilly thinks of as a “New Canaan.” A few months later, they go to an art gallery to look at a Van Gogh, and Tadg is shot to death while standing next to Lilly, and Lilly must go on the run again.
Penniless and desperate, Lilly finds her way to Cleveland and spends some time begging. She collapses outside the building where a black man named Catus Blake lives; he takes pity on her and carries her inside and calls his daughter, Cassie. Cassie works for a wealthy woman named Mrs. Wolohan, and secures a job for Lilly in the household. Mrs. Wolohan is compassionate, and working there Lilly finds stability and some happiness, becoming best friends with Cassie.
Lilly meets policeman Joe Kinderman, who romances her. She finds Joe fascinating—he is very American, filled with confidence. She marries Joe, and becomes pregnant, but Joe disappears, purposefully abandoning her. Lilly has her son, Ed, on her own in Cleveland hospital. Mrs. Wolohan, who has now become one of Lilly’s great friends as well, cares for her and protects her. The Wolohans move to Washington D.C. and Lilly experiences some of the events of the Civil Rights movement directly, with Cassie’s experience informing her own impressions of personages like Martin Luther King, Jr.
The Vietnam War swells into a quagmire, and her son Ed goes off to fight. Lilly recalls how her brother Willie went to fight in World War I. When Ed returns he is shattered and changed, and distant from his mother. Ed has a son named Bill, who he cannot care for, leaving his raising to Lilly, who becomes devoted to him. The Wolohans move to Long Island, taking Lilly with them, and this is where Lilly spends the rest of her life, retiring there and staying in touch with the Wolohans who continue to be great friends to her. Bill is pulled into the Gulf War, and his experience is similar to his father’s; he returns changed and unhappy, and eventually commits suicide.
Lilly contemplates how war—the Irish War of Independence, World War I, World War II, the Vietnam War, the Gulf War—has destroyed so much in her life. She contemplates the pills she has acquired for her suicide but decides against taking them. The book ends without making it clear whether Lilly dies anyway or not.