I googled the last two lines of my error and found this:

https://stackoverflow.com/questions/37495375/python-pip-install-throws-typeerror-unsupported-operand-types-for-retry

Apparently, the issue is a really old version of pip3 that comes with 
Raspbian.  

I followed these instructions to get a new version of pip.  A normal pip 
upgrade might have worked as well.

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


On Wednesday, May 22, 2019 at 7:51:46 AM UTC-4, Ryan Krauss wrote:
>
> I am trying to install jupyter on the latest version of Raspbian and I am 
> running into this problem:
>
>  sudo pip3 install jupyter
> Collecting jupyter
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
>   Using cached 
> https://files.pythonhosted.org/packages/83/df/0f5dd132200728a86190397e1ea87cd76244e42d39ec5e88efd25b2abd7e/jupyter-1.0.0-py2.py3-none-any.whl
> Collecting notebook (from jupyter)
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
>   Using cached 
> https://files.pythonhosted.org/packages/f6/36/89ebfffc9dd8c8dbd81c1ffb53e3d4233ee666414c143959477cb07cc5f5/notebook-5.7.8-py2.py3-none-any.whl
> Collecting nbconvert (from jupyter)
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
>   Using cached 
> https://files.pythonhosted.org/packages/35/e7/f46c9d65f149271e47fca6ab084ef5c6e4cb1870f4c5cce6690feac55231/nbconvert-5.5.0-py2.py3-none-any.whl
> Collecting qtconsole (from jupyter)
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
>   Using cached 
> https://files.pythonhosted.org/packages/c7/45/1a50288305797fbca7c2039f9baefff1a9df603322874743fbb8408d8ec2/qtconsole-4.4.4-py2.py3-none-any.whl
> Collecting ipywidgets (from jupyter)
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
>   Using cached 
> https://files.pythonhosted.org/packages/30/9a/a008c7b1183fac9e52066d80a379b3c64eab535bd9d86cdc29a0b766fd82/ipywidgets-7.4.2-py2.py3-none-any.whl
> Collecting ipykernel (from jupyter)
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
>   Using cached 
> https://files.pythonhosted.org/packages/a0/35/dd97fbb48d4e6b5ae97307497e31e46691adc2feedb6279d29fc1c8ad9c1/ipykernel-5.1.1-py3-none-any.whl
> Collecting jupyter-console (from jupyter)
>   Cache entry deserialization failed, entry ignored
>   Cache entry deserialization failed, entry ignored
> Exception:
> Traceback (most recent call last):
>   File 
> "/usr/share/python-wheels/urllib3-1.19.1-py2.py3-none-any.whl/urllib3/connectionpool.py",
>  
> line 594, in urlopen
>     chunked=chunked)
>   File 
> "/usr/share/python-wheels/urllib3-1.19.1-py2.py3-none-any.whl/urllib3/connectionpool.py",
>  
> line 391, in _make_request
>     six.raise_from(e, None)
>   File "<string>", line 2, in raise_from
>   File 
> "/usr/share/python-wheels/urllib3-1.19.1-py2.py3-none-any.whl/urllib3/connectionpool.py",
>  
> line 387, in _make_request
>     httplib_response = conn.getresponse()
>   File "/usr/lib/python3.5/http/client.py", line 1198, in getresponse
>     response.begin()
>   File "/usr/lib/python3.5/http/client.py", line 297, in begin
>     version, status, reason = self._read_status()
>   File "/usr/lib/python3.5/http/client.py", line 266, in _read_status
>     raise RemoteDisconnected("Remote end closed connection without"
> http.client.RemoteDisconnected: Remote end closed connection without 
> response
>
> During handling of the above exception, another exception occurred:
>
> Traceback (most recent call last):
>   File "/usr/lib/python3/dist-packages/pip/basecommand.py", line 215, in 
> main
>     status = self.run(options, args)
>   File "/usr/lib/python3/dist-packages/pip/commands/install.py", line 353, 
> in run
>     wb.build(autobuilding=True)
>   File "/usr/lib/python3/dist-packages/pip/wheel.py", line 749, in build
>     self.requirement_set.prepare_files(self.finder)
>   File "/usr/lib/python3/dist-packages/pip/req/req_set.py", line 380, in 
> prepare_files
>     ignore_dependencies=self.ignore_dependencies))
>   File "/usr/lib/python3/dist-packages/pip/req/req_set.py", line 554, in 
> _prepare_file
>     require_hashes
>   File "/usr/lib/python3/dist-packages/pip/req/req_install.py", line 278, 
> in populate_link
>     self.link = finder.find_requirement(self, upgrade)
>   File "/usr/lib/python3/dist-packages/pip/index.py", line 465, in 
> find_requirement
>     all_candidates = self.find_all_candidates(req.name)
>   File "/usr/lib/python3/dist-packages/pip/index.py", line 423, in 
> find_all_candidates
>     for page in self._get_pages(url_locations, project_name):
>   File "/usr/lib/python3/dist-packages/pip/index.py", line 568, in 
> _get_pages
>     page = self._get_page(location)
>   File "/usr/lib/python3/dist-packages/pip/index.py", line 683, in 
> _get_page
>     return HTMLPage.get_page(link, session=self.session)
>   File "/usr/lib/python3/dist-packages/pip/index.py", line 792, in get_page
>     "Cache-Control": "max-age=600",
>   File 
> "/usr/share/python-wheels/requests-2.12.4-py2.py3-none-any.whl/requests/sessions.py",
>  
> line 501, in get
>     return self.request('GET', url, **kwargs)
>   File "/usr/lib/python3/dist-packages/pip/download.py", line 386, in 
> request
>     return super(PipSession, self).request(method, url, *args, **kwargs)
>   File 
> "/usr/share/python-wheels/requests-2.12.4-py2.py3-none-any.whl/requests/sessions.py",
>  
> line 488, in request
>     resp = self.send(prep, **send_kwargs)
>   File 
> "/usr/share/python-wheels/requests-2.12.4-py2.py3-none-any.whl/requests/sessions.py",
>  
> line 609, in send
>     r = adapter.send(request, **kwargs)
>   File 
> "/usr/share/python-wheels/CacheControl-0.11.7-py2.py3-none-any.whl/cachecontrol/adapter.py",
>  
> line 47, in send
>     resp = super(CacheControlAdapter, self).send(request, **kw)
>   File 
> "/usr/share/python-wheels/requests-2.12.4-py2.py3-none-any.whl/requests/adapters.py",
>  
> line 423, in send
>     timeout=timeout
>   File 
> "/usr/share/python-wheels/urllib3-1.19.1-py2.py3-none-any.whl/urllib3/connectionpool.py",
>  
> line 643, in urlopen
>     _stacktrace=sys.exc_info()[2])
>   File 
> "/usr/share/python-wheels/urllib3-1.19.1-py2.py3-none-any.whl/urllib3/util/retry.py",
>  
> line 315, in increment
>     total -= 1
> TypeError: unsupported operand type(s) for -=: 'Retry' and 'int'
>
>
> Any help would be appreciated.
>
> Thanks,
>
> Ryan
>

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