On Oct. 12, 2005, Apple and Disney surprised the media industry with a landmark Disney‑Apple deal that changed expectations for how viewers could access primetime TV. The agreement made it possible for consumers to buy primetime programming digitally for mobile devices — without needing an antenna or a multichannel subscription — a first-of-its-kind move that foreshadowed today’s on‑demand streaming economy. Twenty years after that pact, former Disney Media Networks co‑chair Anne Sweeney looks back on her role in negotiating the agreement and the high‑stakes conversations she had with Steve Jobs. Sweeney’s reflections underscore how the Disney‑Apple deal was not only a business milestone but also a cultural turning point, demonstrating what can happen when a major entertainment studio and a technology leader align on distribution and consumer access. The 2005 agreement mattered because it anticipated consumer demand for portable, purchase‑based access to television content. By enabling digital purchases on mobile devices without requiring traditional broadcast antennas or subscription bundles, the deal accelerated industry thinking about direct‑to‑consumer distribution and helped lay groundwork for later developments in streaming, digital storefronts, and device‑based content ecosystems. Sweeney’s recollections also highlight the complexity of negotiating across two very different corporate worlds: legacy media and Silicon Valley tech. The collaboration required clear strategy, legal and technical coordination, and an appetite for risk as both companies tested new territory for monetizing TV content. Two decades on, the Disney‑Apple deal remains a notable chapter in the evolution of media distribution. For executives and industry watchers, Sweeney’s account offers lessons about vision, partnership, and the long‑term impact that bold distribution moves can have on how audiences watch television.