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Originally Posted by Le Grande Orange
Hmmm, I've always read the term as simply applying to leagues not part of the national agreement/organized baseball, not necessarily to those which raided other leagues for players. But I defer to your more in-depth knowledge in this regard.
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Most of the latter-day examples of independent leagues before the current batch -- the post-WWII Mexican League, the various leagues in Vermont and Quebec, and so forth -- were indeed outlaw leagues. Earlier, there were examples of leagues that didn't go a-raiding other leagues.
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Personally, it seems to me much of OOTP's growth in terms of features and capabilities has been done on an ad hoc basis rather than necessarily with any long-term specific goal or vision in mind. Users request certain features, Markus codes them in, adds a few things which interest him, puts out the game, which in turn garners more feature requests, and so on.
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That is my impression as well.