Drilling a whole in a HUGE clay vessel

Hi folks,
I bought a 4 ft tall Strawberry pot. It does not have a drainage hole in the bottom. After our most recent rain I noticed it had > 4" of water in the base. Does anyone have any recommendations/tips/cautions on how to do this & what tools to use?
The pot is unglazed red clay w/ a rather coarse texture. The texture is the same/similar as that of much smaller glazed pieces I've seen from Mexico. It appears to have been wheel thrown and the cut in half based on the central disc marking on the inside bottom but I don't recall seeing throw marks on the sides. I can get a photo when it's light if it matters. I was thinking if it was thrown, the clay particles have developed a particular orientation and might be more prone to breakage if the sides were interrupted.
My DH was wanting to leave it on its' platform and drill holes on the bottom of the sides of the pot. I think that will weaken the sides as well as spoiling the look. The only advantage I see to doing it this way is the pot took 3 strong men to position on the platform which is itself a matching giant clay plant pot saucer turned upside down. We discussed 3 of us (not particularly strong folks) tilting it at an angle on the saucer/platform & then one of us drilling out a 1" drain hole in the bottom while the other 2 stabilized it. I think we woud have to drill several/many small holes in a circle and then tap it out.
Has anyone here done this or similar before? We had considered practicing on standard clay pots to get a feel for the whole procedure. Any idea how the texture difference would affect how we should proceed?
Thanks in advance,
Maggie