Python PIP Install throws TypeError: unsupported operand type(s) for -=: ‘Retry’ and ‘int’

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Ubuntu comes with a version of PIP from precambrian and that’s how you have to upgrade it if you do not want to spend hours and hours debugging pip related issues.

apt-get remove python-pip python3-pip
wget https://bootstrap.pypa.io/get-pip.py
python get-pip.py
python3 get-pip.py

As you observed I included information for both Python 2.x and 3.x

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