Can an "ugly", badly conformed horse win in a Showmanship Class?

I think you should go for it! He looks old but appart from that he is a very handsome boy :). Showing him will make good use of his 'light riding' as it will only be a few minutes. Love his colouring btw

I have no idea about showing but he's a gorgeous looking boy:)
Go for it and see how it goes:) it would be good fun for both of you
Best of luck

The answer to this question is yes. I showed a mediocre built, sway backed 24 year old in showmanship quite successfully when I first got into horses.

I totally agree with this, I've been told that a judge puts about less than 5% of their judgeing on the horses confo (This could vary from association to association) then a LARGE part on your pattern and the presentation of your horse and yourself . I personally believe you could totally win at a local level as far as higher than that I am honestly not sure, it all depends on how much work you put into him. Also if you do some schooling shows don't be afriad to approach the judges at appropreat times to ask for improvement suggestions