Newton's Wake ISBN 0765305038
His books use science fiction partially as a forum to explore political ideas. TheStarFraction has some emphasis on communism, within the framework of a society that has some similarities to that of NealStephenson's SnowCrash. TheStoneCanal explores anarchism/AnarchoCapitalism.
It's not all dead serious. As a fillip, Mr. MacLeod also lightly salts his novels with subtle in-jokes.
TheStoneCanal has a well-written passage portraying a surprising use of BootStrapping.
TheStoneCanal may have been inspired in part by DavidFriedman's 1971 The Machinery of Freedom ISBN 0812690699, a libertarian guide to AnarchoCapitalism. Note the similarities: one of the main characters of TheStoneCanal is David Reed (who is a major proponent of AnarchoCapitalism), and the title of the first part of the novel is "The Machinery of Freedom". Mr. Friedman is also reputed to be a SF fan.
If you are referring to David Director Friedman, he is indeed an SF fan, among other things. Wikipedia link [http://en.wikipedia.org/wiki/David_D._Friedman]CategoryAuthorCategoryScienceFiction