The period from 2016 to 2022 marked a decisive shift in Doctorow's intellectual project, from defending individual digital freedoms to diagnosing structural economic power. The enemy in his earlier work was DRM and bad copyright law; in this era it became monopoly, concentration, and the chokepoint-capitalism that lets a handful of platforms extract rents from creators, workers, and users alike.
walkaway (2017) was the inflection point in his fiction: a utopian novel about people who opt out of a hyper-concentrated economy and build open, redundant, federated alternatives. It was the most ambitious and explicitly political thing he had written, and its diagnosis of platform-decay-cycle dynamics anticipated the framework he would name enshittification a few years later.
The collaboration with rebecca-giblin on chokepoint-capitalism-book (published at chokepoint-capitalism-published-2022) synthesized the political economy argument most fully. The book examined how chokepoint-capitalism operates across music, books, news, and other creative industries: a small number of buyers or distributors use their bottleneck position to extract value from creators while degrading the product for audiences.
This era also saw Doctorow's engagement with the new antitrust movement, connecting his work to lina-khan's platform monopoly theory, matt-stoller's industrial policy arguments, tim-wu's work on concentration, and zephyr-teachout's advocacy. The launch of pluralistic-net in 2020 was itself an act of building infrastructure that embodied the alternatives he was describing: direct audience relationships, no algorithmic mediation, no platform intermediary.
radicalized and attack-surface continued developing themes from little-brother while incorporating the sharper class-analysis of this period.