It probably went down like this:
Sergey: "hey Jimmy, how much do I have to pay you NOT to see your creepy face on every wikipedia article?"
Jimmy: "Well...."
Sergey: "hey Jimmy, how much do I have to pay you NOT to see your creepy face on every wikipedia article?"
Jimmy: "Well...."
Seriously, why are so many people complaining about this?
Or, you can download the content freely and see it any way you prefer.
Those seem like a couple reasonable options, to me.
What makes me a bit uncomfortable is that these ads associate Wikipedia very strongly with a single person.
(I'm sure there are people who think Wikipedia is neither independent nor objective; I have no informed opinion on that. But for argument's sake, let's assume that it is and that this is what the contributors strive for)
A personal appeal seems reasonable to me. People are accustomed to getting content for free and not asking questions, and sometimes need to be reminded that it takes people and work to keep the quality content coming.
So which people to use? They can't show pictures of individual contributors, because they won't be the ones receiving the donations. Jimmy Wales is the primary person responsible for stewarding your donation for the greater good[1], so showing his picture makes sense to me.
[1]: For instance, if there were some hypothetical financial scandal, he's the one that everyone would be mad at.
I have donated to Wikipedia in the past -- even before Wikipedia was a household name (which isn't something I say to seem like some hipster schmuck, but to illustrate that I believe enough in what Wikipedia does to donate my money at a time when it was uncertain if they would even survive -- let alone be successful).
Whenever I see Jimmy Wales' face in the current ads my gut reaction is that I'm not going to contribute to his blatant self-promotion.
I don't know Mr Wales and I have no opinion on him as a person, but I can't help but recoil every time I see his face on Wikipedia. It just doesn't bring out the philanthropist in me. Sorry. I'm probably a bad person. Or something.
If Wales was really fond of self-promotion, he could have done a lot more. He probably wouldn't have set up a foundation with an elected board of trustees which runs the foundation in his stead.
I find it more likely that this is just the Wikimedia Foundation trying to give a humane face to Wikipedia in order to get more donations. It might be a misguided move, but I don't think Wales is excessively pushing for it.