Back a few years I was chewing the fat over a beer with RJP and we were talking about the (International) Radiotelephony Spelling Alphabet, as you do. It’s the main way to remove ambiguity in communications that can arise from pronunciation of words or letters. You will have heard it at some point otherwise you are either delta uniform mike bravo or have been living in a charlie alpha victor echo. First letter of the phonetic words is the letter you are trying to convey and none of the words sound the same. Great idea!
It occurred to us that it should be possible to create the exact opposite of the phonetic alphabet – a phonetic alphabet designed to maximise confusion when used to spell out words. We lean heavily on homonyms and silent letters to make the most confusing alphabets. We strictly stick to the rule that the confusing word must start with the letter it represents. Won, kew, eye, etc are all in there.
We rapidly came up with a prototype and there it stayed for a decade or so, but it’s now hit the website as a generator. It will create a confusing phonetic alphabet for you at each refresh. Sprinkled with the official words, if you want! As with most of my generators you can pop a ?help on the end to see what options you have.