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Cove, that was exactly my objection to his shirt. It was the use of a firearm to promote evil, not to simply have as a tool.

You would be surprised what some people let their children do. Some people think these ways themselves. After teaching, you start to believe that some people should get fixed.
Most of my students do come from good homes, where parents would never allow that mess.
Motorcycles are very popular around here, so I see biker stuff all the time. It doesn't bother me. Biker items don't carry the gang connotation that they did in former times. Most bikers are people like my dad & uncles that just like to get wind in their faces.
Heck, my pastor is even a biker.

The individual on his shirt was some singer dressed in a 1920s gangster outfit throwing popular gang hand signals. It was not the bald gentleman with a contented look on his face in the picture you posted.

I try to teach them right from wrong in the short time I have them.

The ones that have had me in previous years know that I'm not an anti-gun freak; when we discuss our hobbies, I let them hear me say that I go to the range and target shoot. I want them all to see that their teacher, a law-abiding citizen, uses guns and doesn't harm people with them.
Sometimes, my students will tell me about deer, boar or wild turkey that they've shot. I'm not into hunting personally, but I let them know it's an accomplishment.
We have a lot of discussions on responsibility for one's own behavior. Middle schoolers often have an innate lack of this understanding. (Anyone that has raised a teen knows this.) We talk constantly about it. I'm always happy when I see it starting to get through. Moral developement is just as important as knowledge in a child's development.
I can't remember who said it, but a famous person once said, "To educate a child in mind and not morals is to educate a menace to society." I believe that fully.

As many of you know, I'm a middle school teacher.
An emotionally disturbed (real title, not being rude) child came to class today wearing a shirt with a machine gun in the hand of a drug thug.
I sent him to the office.
I told my assistant later that I felt weird sending the kid to the office with a gun on his shirt, but just couldn't stomach a drug thug holding it so proudly.
After he left, I gave the kids a talk about what kinds of things drug lords do to people that cross them. I have a real problem with criminal behavior, and let the kids know that many of these people are worse than the terrorists that we're fighting.