This one certainly goes way up toward the top.
I would also nominate the statue of Kirby Puckett outside of Target Field - it originally looked like a bear, then they slimmed the face so that it looks 50% better, but still not much like Puckett. (One issue they may have is their desire to capture Puckett in game 6 of the 1991 Series as he was screaming rounding the bases - the statue should have been of Puckett stading in the batter's box, smiling. That is how everyone remembers him).
The other one - that statue of #23 outside United Center. I had no idea that Terry Porter was a star for the Bulls at some time in his career.