Actually it's possible... http://half-wit4u.blogspot.com/2011/05/skype-using-java-api-skype4java.html But formatting would help out a bit.
i think is wonts something like this: http://forums.bukkit.org/threads/mi...ct-minecraft-and-teamspeak3-1-3-1-r1-0.65971/
lol... I didn't know @Firedroide put me on there (third line). Which reminds me I have to get that Bukkitdev page switched over.
Maybe someone can write a Skype addon and write a plugin that connect bukkit and the Skype addon. But that will take more then one programming language. I think C or C++ (for the skype addon) and Java (for the plugin). Or write a plugin that is a minimalistic version of Skype. So the plugin send messages directly to the Skype client.
Yah atm I don't believe I can write it. Maybe soon. (a week I travel alot) Inbetween getting the classloader to load up the jar libraries. The libraries linking to correct dll versions then those dll's calling back to the jar libraries and running through the a huge Group of connecting systems. I finally found my stopping point. In theory I could package it for linux,osx,and win32 but I'm quite a distance away from my Debian machine and running on theories untested are difficult and require a huge amount of patience from all the hate spam stacktraces from users. Basically you would have to have Skype running along side the server and the plugin and all its connecting glory would talk to skype and listen on its api. I believe I made it through all the connectors assuming that skype.dll is the library for the skype program itself (Just checked, it is.) So I'm working on theory. If anyone has a 32 bit machine or operating system I have 2 classes I wrote that will send and recieve Chat from skype. As for configuration your on your own.
Programs such as Trillian connect to multiple chat providers without having to have an addon on the receiving end.
Alright. I finished. However formatting a little more would help considering right now it just transfers chat. Keep in mind that this will not work with 64-bit Java and you must have Skype running on the server. I just remembered this and figured I'd finish it. Source: https://github.com/deathmarine/BukkitSkype Download: https://github.com/downloads/deathmarine/BukkitSkype/BukkitSkype.jar No Configuration, No Commands, No Hassle just drop it in and all messages will be sent to your friends.