Four out of every five vehicles towed in Chicago for snow-related parking violations were seized on days without accumulation of snow. Either unwilling or unable to satisfy the debts required to recover their cars, hundreds were never recovered. Synthesising multiple sources of public data over a five-year span (2013–2017), the authors show how these towing practices disparately devastate segregated communities of colour through impositions of debt and dispossession. Who profits from these impositions? The same politically connected company that represents one of Chicago’s first attempts at privatisation. United Road Towing landed the exclusive city contract in 1989, only nine days after the company’s creation, and its ascendance to Chicago’s political scene stood upon a white racial imaginary that linked parking violations to threats of urban decay. Through a euphemistically named public–private partnership, United Road Towing has since become one of the largest towing companies in the world. This article is an inquiry that parses out a concept the authors label as ‘public–private predation’ by historicising Chicago’s commodification of the streetscape, theorising how racialised hardship results from the draining of neighbourhood resources and quantifying which segregated communities are subject to these new sites of extraction – all within a world of winter parking regulations.