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Well, no history of outliners can call itself complete without mentioning Ecco Pro (see e.g. https://en.wikipedia.org/wiki/Ecco_Pro), which from my humble point of view was "the mother of all modern outliners". Sure there were earlier ones like the mentioned More, but Ecco was a much more powerful tool. Unfortunately the development of Ecco was discontinued in the late nineties, but I used it for another ten years e.g. as an information management tool in some big government projects, but eventually I built my own tool, which inherited a lot from Ecco, but also added things I missed (see https://github.com/rochus-keller/CrossLine).