I hear from the responses that nobody is interested because there's no payment, no trust because you don't know me, and nobody quite understands why anyone would draw for Wikipedia, or why Wikipedia would want drawings in the first place. Fair enough.
To address those concerns:
*Sure, there's no payment, and maybe the exposure would bring no jobs either. I thought it might. I also thought artists like to see their work appreciated and "seen", like the wonderful BANKSY.
*I am sorry, by the way, about the money thing. Artists are wonderful, and at the best of times, often have trouble making a living. The opposite end of the spectrum is hedge fund managers. They create nothing and get everything. It is not fair. Plus, you don't have a choice. True artists can be nothing but artists. So, sorry about the money. You deserve to everything. I, personally, am a lousy pseudo-artist. You can search my userpage at Wikipedia: "Anna Frodesiak".
*I am new here. But I have been around Wikipedia for years and am an administrator there. I am trustworthy.
*A decent likeness is way better than no image at all. Wikipedians (and almost certainly article visitors) would agree.
*Money, eh? I wonder if Wikipedia would cough up some money. They have 20 million or something now. Maybe I will ask.
*So, how about one image? A drawing. 10 minutes. See how it goes. You may like it. It may turn out to be something wonderful. And what do you have to lose? 10 minutes drawing must be more fun than 10 minutes at a forum, right?
*Could you suggest a place for me to contact? Some groups somewhere?
It goes even beyond the working-for-free thing, I don't think I even understand the concept behind what was proposed. If I were on the Wikipedia page of say, Caitlyn Jenner, like you mentioned in the example, I would not want to see someone's drawing of her. I would want to see a photo, not some artist's sketch. Even if they were super talented.