Okay, I was skeptical about this thread when I first saw it, but now I see the awesome potential for teaching physics here.
You can't "diffuse the pressure". At every point along the wall of a sealed vessel, the pressure is constant. So if, e.g., the pressure of the hole when sealed would be 100 PSI, then to stop it every square inch of the seal needs to withstand that 100 PSI.
If the top of your concrete cylinder has, say, 100 times the area of the hole, then the flow of oil may end up evenly distributed over that area. But if you then try to seal the top you must now provide the same strength of seal -- it must withstand the same pressure -- over a much larger area, which is probably harder to accomplish.
This seems counterintuitive, just as the lever is counterintuitive. But we use this principle all the time to lift things like elevators and cars. You push on a tiny-diameter cylinder with your arms (or with a little electric motor), and it pumps fluid into a much larger-diameter cylinder under the car, and the car rises. Of course, you have to pump up and down dozens or hundreds of times to lift the car one inch.