No matter his situation, Humberto Brause (Daniel Hendler) greets everything that happens to him with the same expression: a stunned, almost dazed stare, his mouth partly open yet silent and his face immobile. Is he thinking things through, figuring a way out? Many times, he is, but Humberto’s tragedy in Federico Veiroj’s bitingly clever The Moneychanger (Así habló el cambista) is that he’s never quite sharp enough to stay a step ahead of his enemies.

Set in the span between the 1950s and ’70s in Montevideo, Uruguay, The Moneychanger is an allegorical spin on the small country’s place between its two neighboring giants, Brazil and Argentina, through the experience of an opportunistic financier. As a neutral territory during those chaotic times, Uruguay becomes immensely attractive for above and below board business deals. When a chance to make a princely sum arrived on his desk, Humberto decides to break from his boss’ advice about running an ethical practice and opts for the more profitable route of money laundering. As his clientele evolves from corrupt politicians to gangsters, Humberto finds out he’s not so clever and his appetite for the good life may actually be leading him to ruin.

The Moneychanger has a dry, witty sense of humor about Humberto’s predicament. His problems never get so serious as dampen the movie’s tone, but there’s a streak of bitter irony in the character’s story. In certain respects, he’s kind of an underdog, one the movie wants its audience to cheer for but whose portrait is less than heroic. He looks down on everyone even as he’s failing upwards. His wife was a conquest, not a love interest; his kids an afterthought. Through the strength of Hendler’s performance, he redeems his sour character from Arauco Hernández, Martin Mauregui and Veiroj’s dark script. The actor gives Humberto a kind of bumbling helplessness – that dumbfounded look with a deer-in-the-headlights pose – that makes him almost sympathetic as if he had jumped into the deep end of the swimming pool without knowing how to swim. He’s a man in over his head, that even if he’s rude to his wife Gudrun (Dolores Fonzi) or fatefully so one-minded in his business, that there’s a part of us that might not want to see him drown.

In certain respects, he’s kind of an underdog, one the movie wants its audience to cheer for but whose portrait is less than heroic.

In addition to his credits as co-producer and co-writer, Hernández also serves as the film’s cinematographer. His visual style gives The Moneychanger its aged air of old Uruguay. It’s a palette full of rich earth tones: deep greens in a forest of brown, like the wooden furniture and sepia-esque light in Humberto’s darkened office and the rocky grays and oceanic navy blues of the businessmen’s suits. Almost every outdoor scene looks as if it were shot under the gloom of a cloudy day – possibly, an omen for its main character’s doomed ventures. A piano-led score by Hernan Segret echoes the downfall of a man with more delusions of grandeur than wits. The Moneychanger is the latest reunion for Hernández and Veiroj, who previously collaborated on Veiroj’s movies, Belmonte and The Apostate.

The great tragedy in Humberto’s life is that his ambitions outpace his criminal talents, and his flaws far outnumber his strengths. Yet, there’s still a vulnerability in him that doesn’t allow him to become the worst of his clientele. Although he dismisses his wife constantly and cheats on her occasionally, there’s still a look of sadness in his face when he asks her if she loves him and Gudrun quips, “Don’t be stupid.” He can’t help himself. We can get caught up in Humberto’s painfully human problems without remembering the film’s dual analogy of Uruguay playing its way to riches between the misfortunes of its neighbors and how it precarious that game was. But it’s that extra layer of meaning that makes Humberto’s saga so enticing.

The Moneychanger screened at the Toronto Film Festival.