Text Box Rotates but Not Text

@Trinity5C08 It looks like you are trying to rotate area type. Illustrator uses point type and area type.

• Area type is when you click the type tool and drag out a box to type in.
• Point type is when you click the type tool and then click the screen and start typing.
• If you use point type, you will be able to rotate it just by hovering over one of the corners. 
• Yours looks like area type so it is rotating within the area of the bounding box. 

If this is confusing, I included a video if you need it. Please excuse the cracking of my voice, it's pretty late where I am. :c) I hope this helps.

If you create a text box, this is the expected behavior. If you want the text to rotate, then use the dialogue box for the text tool. If you don't create a text box, however, when you select the text and get the baseline, the text will rotate. Perhaps that is what you are thinking of?

Has always been like that.

You need to use the rotate tool to rotate area text.