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Honestly python won in large part because perl took over a decade to come out with perl 6. Knowing that there was a backwards-incompatible upgrade on the horizon shortly and having that be true for a decade meant that new projects in perl or major upgrades in perl were delayed and then shifted to projects in other languages. Python and ruby both were beneficiaries of this (especially with PHP going through a similar process with PHP 6 which took 5 years before being abandoned.)

Cough. Python 3. Cough.

(I don't dispute the majority of your point, but I don't think all 10 year, backwards-incompatible upgrades are created equal.)

Agreed. The main difference is that development of python 3 didn't stop development on the 2.x branch until 3.4(?) was out. There was also an upgrade path and the ability to support both Python 2 and Python 3 at the same time. Python 3 could _easily_ have been a similar roadblock but was handled well enough to avoid that fate (better upgrade tooling would have been a massive help)

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