This may help.
I think the issue here goes back to the fact that pi is a ratio of circumference to diameter. This seems fine, we're trying to see how many times your diameter will go around your circle, and that number is 3.14... times. Fine. Good. But wait, we always use the radius, not the diameter for calculations. So wouldn't a ratio of the circumference to the radius be more useful? Well that's another story, but it explains why RADIANS are so confusing for some.
You see, when we say that 2pi is a full circle, or 360 degrees, it seems odd. Why does it take 2pi radians (a type of angle measurement just like degrees but arguably scaled down) to go all the way around the circle?
The answer has a lot to do with the fact that a RADIan comes from the RADIus. That's where the word radian comes from, because when you've gone 1 radius length around your circles perimeter, the angle will be 1 radian. when you've gone pi radius lengths around your circle, its no surprise that the angle you get is pi radians, which will be a flat line.
This is, again, because if it takes pi number of diameter lengths to go around a circle, it will take 2pi radius lengths to go around the circle. This is why 2pi is 360 degrees.
As far as generating the value pi is concerned, the oldest way that requires no self-reliant definition is the method used by Archimedes. While granted this is basically early integration, Archimedes was simply using geometry. If you take a hexagon, and look at its perimeter to diameter ratio, you'll get 3. If you look at higher and higher numbered polygons, like a 17-gon, that ratio of circumference to diameter will slowly reach 3.14... which is exactly what you'd expect since a circle is just an infinitely sided polygon. Its a bit more complicated since he used both inscribed and circumscribed polygons to get an even better limit, but you get the gist. This isn't a great way to calculate pi, but Archimedes did it up to a 96-gon, and you can technically continue on this path infinitely to get pi definitionally. This was the first fully recorded estimation of pi in the western world to such an accuracy.
Didn't cheat did I?