Well, if the War of the Ring ended in Sauron's victory and he gained the ring, Gandalf probably would challenge Sauron, but he would lose, probably very badly. What exactly do you mean, "he wasn't allowed at first"?
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"What mortal feels not awe/Nor trembles at our name,
Hearing our fate-appointed power sublime/Fixed by the eternal law.
For old our office, and our fame,"
-Aeschylus, Song of the Furies
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