Full disclosure: I work at Braintree. If you have any further questions, feel free to contact
support.
The "retries exceeded" error seems to be a red herring that really points to an SSL incompatibility. The SSL: TLSV1_ALERT_PROTOCOL_VERSION
SSLError indicates that the host url api.sandbox.braintreegateway.com will not accept your TLS version.
Starting on December 16, 2016, Braintree deprecated Sandbox's support of TLSv1.1 in favor of TLSv1.2, you can read about it in this blog post.
To fix this issue, you will want to check which version of OpenSSL your machine is running using Terminal:
$ python3 -c "import ssl; print(ssl.OPENSSL_VERSION)"
If the OpenSSL version is not 1.0.1+, you will need to update OpenSSL to the latest version, which supports TLSv1.2. If you are using Homebrew, you can follow the instructions outlined here.