The Mastermind opens with a richly ironic tone, introducing a protagonist who is anything but masterful. James, the central figure, is a hapless and deluded man whose poor decisions set the stage for Kelly Reichardt’s bleak yet engrossing heist drama.
Set in 1970s Massachusetts, the film subverts expectations of the genre, presenting not a slick criminal genius but a man unraveling under his own misguided fantasies. By the film’s end, James resembles a character from a John Updike novel—fleeing from consequences with nothing but shame and confusion.
A Flawed Dreamer Fueled by Privilege, Delusion and a Desperate Need for Validation
James is played with a sad, near-charming ineptitude by Josh O’Connor. An art school dropout and would-be designer, he’s deeply reliant on his patrician parents. His father, a stern judge, and his wealthy mother fund his supposed creative ambitions. However, his dependency masks darker motives.
While his wife Terri (played by Alana Haim, regrettably underused) and children form the facade of a stable life, James is secretly plotting an ill-conceived art theft. His fragile masculinity and delusions of grandeur become the true driving forces of the narrative.

Unlike traditional heist films filled with glamor and adrenaline, The Mastermind is resolutely grounded. James’s plan involves hiring thugs to steal paintings by Arthur Dove, but his lack of foresight quickly becomes apparent—he doesn’t even have a viable plan to sell the stolen art.
Reichardt’s unvarnished style makes the violence and chaos more disturbing, using muted tones and natural lighting to strip the crime of any excitement. There’s no soundtrack to romanticize the act; just the grim, awkward reality of people committing crimes they barely understand.
After the Heist A Portrait of Collapse, Delusion and Unfulfilled Artistic Dreams
The real narrative weight of The Mastermind lies in its aftermath. James’s poor planning leads to unraveling alliances, growing paranoia, and the creeping presence of local mob retribution. Like in Museum or American Animals, there’s a documentary-like attention to detail, but Reichardt takes it further—she’s more interested in the fallout than the crime itself.
James stumbles through the wreckage of his plan, interacting with friends and family who are confused, alarmed, or repelled by his actions. The heist becomes a backdrop for examining failure, both personal and systemic.
Reichardt’s thematic focus on the mundane aspects of art and everyday existence remains prominent, echoing her approach in Showing Up. In The Mastermind, artistic ambition is stripped of any romanticism and instead revealed as a cover for self-interest and delusion.
James’s misguided sense of purpose reveals how deeply he misinterprets both creativity and responsibility, using the guise of artistry to justify reckless and selfish behavior. As the moral pressures of the Nixon era intensify around him, his story culminates not in redemption but in a harsh and poetic collapse. Reichardt crafts a quiet yet powerful portrait of a man desperate to matter, who ultimately exposes just how insubstantial he truly is.

