Well, when a guy is running on a platform of being as American as mom and apple pie, it wouldn't look good for him to be using all kinds of offshore tax havens and loopholes.

I think it is more about the aggressiveness if their loophole exploitation than mere thickness.

Just like I encourage my tax man to find every possible way for me to reduce my tax burden, I would expect everyone to do that. A loophole is a legal way to do that. If a person has the know-how to aggressively find and use the resources available to them... that shows a great deal of character to me. Don't hate the player... hate the game. You have a problem with a loophole, lobby to get it closed. Or use it also. But I imagine this view is not shared by everyone.