The following version of this book was used to create the guide: Cunningham, Vinson. Great Expectations. Hogarth, 2024.

Vinson Cunningham's novel Great Expectations is set in 2007 and 2008 and written from the first person point of view of the main character, David Hammond. David's experiences working on an Illinois senator's presidential campaign dictate the course of the narrative. However, Cunningham toys with linearity throughout the novel to enact David's complex internal experience. For the sake of clarity, this guide relies on the present tense and a more streamlined mode of explanation.

When David Hammond is 20 years old, his college girlfriend informs him that she is pregnant. David panics and breaks up with her. In the weeks following, he cannot focus on his schoolwork and soon fails out of his program. He and his ex move back to New York where they are from, but do not get back together. Shortly thereafter, David's daughter is born. He spends every other weekend with her, but he and his ex rarely speak.

David is living on the Upper West Side with his mother. When he is not home or spending time with his daughter, David tutors a young boy named Thadd Whitlock. One day, Thadd's mother Beverly Whitlock suggests that David start working for an Illinois senator's presidential campaign. David knows about the young Black Senator and has heard him speak on television. A young Black man seeking direction himself, David agrees to interview with a campaign finance director named Jill Hunter. Jill quickly hires David and introduces him to campaign life.

Over the following weeks, David tries to orient to the world of politics. He learns how to communicate on the job, but struggles to maintain punctuality and clerical order. However, Jill is pleased with him because David has brought in a lot of money with Beverly's help.

A few months later, the campaign sends David and his coworker Howland to Manchester, New Hampshire. David enjoys this trip, as the Manchester workers and headquarters are more animated than in New York. He soon befriends and starts sleeping with another campaigner named Regina. He and Regina spend all of their free time having sex and swapping stories at Regina's apartment. However, they have to say goodbye when David's time in Manchester ends.

David is then sent to Los Angeles. In LA, an old high school acquaintance brings David to a flea market. David is moved when he discovers a vendor selling old photographs. Afterwards, he returns to his dank hotel and lies awake reflecting on his past. Then one of the LA campaigners, Alexis, invites him to go clubbing. At the nightclub, David gets drunk and high and witnesses two men get into a fight. The next morning, David struggles to hide his hangover at another fundraising event. After the event, David meets up with Beverly. She takes him to her hotel and they have sex.

Back in New York, David starts spending all of his downtime with Beverly. However, he soon discovers that Beverly and a campaign contributor have been discovered for illegal activity. Beverly stops contacting David and David fears he will be implicated in the scandal too. However, the news soon fades away as Election Day approaches.

On Election Day, David and Howland fly to Chicago. Before convening in Grant Park to hear the results, David takes a cab to his old church. He spent a few years in Chicago when he was young. The church is abandoned and has relocated to a new building. David finds the new church and prays outside. Back at Grant Park, he learns that the Senator won. He studies the Senator with his family on stage, realizing that he might just be a symbol. David hopes he can be more to his own daughter.