User blog comment:Akali/Ideas for Legendaries/@comment-5514182-20121126045149/@comment-5410699-20121126101618

Well, Teemo is regarded by the community as one of the cutest characters in the game (despite being one of the most hated as well). it also helps that he is also one of the most played (if not the most played) champion in th game.

This enables Riot for easy marketing.

The more popular champ, the more likely that champ will get more skins.

For Example: Take Trundle, Udyr, Soraka, Sejuani, Skarner, Rumble... they have been in the game for quite a while (some more than others, Sejuani being the youngest and she's almost year old) and they have less than 3 additional skins. As most of them aren't played very often.