I believe the disconnect is that Winner does not ask us to "read" artifice in the way deconstruction (for example) compels us to _read_ a text. To critically analyze the political narrative implicit in it. Winner's Project does require what I would call "attentiveness" of us; a word that has political meaning for me. But it is different in important capacities. First, Winner's object of scrutiny is not just the obscured political narratives that get "trojan horse'd" into our approved entertainments like Dick Wolf's "Law & Order" catastrophe. It's the way technologies and artifacts practicably _malign us_ or otherwise deteriorate the material quality of life of various moral patients. The fabric of architecture and civil engineering in our cities is replete with these sorts of political artifacts. Often their design anticipates the criminalization of dissent, and is calculated to suppress popular rebellion. Janson's history of architecture has described Haussman's thoroughfares in Paris as "robust" and "noble," without attention to the fact their metrics were a direct response to Louis Napoleon's efforts to head off a repeat of the organized marches and armed fighting of the 1848 revolution. University architecture in the US was fundamentally altered by the 1960's. It's public spaces are commonly embedded with features designed to facilitate the quelling of student political protests. If you live in a large American city, cances are fair that you've walked or driven through something with metric limits set by the turning radius of a tank.
I don't mean to implicate military authoritarianism here. The political objectives of design often serve more localized or private economic or power interests. Robert Moses' city planning and civil engineering projects are a useful point of reference because people seem to know him as a villain. They know him for his collusion with a burgeoning automobile industry to dismantle the infrastructure of public transportation, and less so for his role in rendering thousands of New Yorkers homeless. But you don't really appreciate him as an evil genius until you've observed how carefully the clearance heights of the Wantagh Parkway underpasses have been calculated to stratify the accessibility of public projects by class status.
The other important distinction in Winner's theory though, is that the political content of our technology isn't always something that happens by conspiratorial _design_. We also seem to become victims of someone's enrichment where emergent or reciprocal relationships occur between technology and certain power interests. Such is the case of Winner's reverse adaptation.