Skype was originally marketed as having end-to-end encryption. Now, we know that since Microsoft bought Skype they've added wiretapping support, which works by making themselves a man-in-the-middle. They claim they only do this temporarily for people they are actively wiretapping.
This, however, shows that Microsoft regularly MITMs you, for the purpose of evaluating whether links are dangerous. This means that basically all of Skype's former privacy claims are no longer true. They simply regularly look at your unencrypted traffic, which means that they are a target for attackers, governments, and pretty much anyone who wants to eavesdrop or read your messages.