Phil,
You do not need the black wire and the bare sheild wire connected to the same terminal. The sheild wire is all that should be connected to the sleeve terminal. The red wire should be the only one connected to the tip terminal.
It's difficult for me to tell which terminal is connected to the tip from your drawing. That's why I suggested buying an inexpensive multi-meter from Radio Shack. This will make the wiring job much easier for you, and additionally, when you and if you encounter equipment problems in the future, you can easily trouble-shoot and isolate the problem.
Here's the connections as I recall them from memory. unfortunately, I do not have a jack in front of me
Gary
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Travlin' Easy
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PSR-S950, TC Helicon Harmony-M, Digitech VR, Samson Q7, Sennheiser E855, Custom Console, and lots of other silly stuff!
K+E=W (Knowledge Plus Experience = Wisdom.)