Sometimes the image says it all; in the 1990s the United States military experimented with skateboards for urban warfare.
In 1993, the American military was one of the parties involved in the Battle of Mogadishu. It did not go well for them (as portrayed in the movie Black Hawk Down) in part because the battle was fought in the middle of a large city. Many of the dominant tactics fall down in urban areas: airstrikes are risky, the terrain isn’t exactly easy for tanks and helicopters to manoeuvre in, and the locals will certainly know the area better than you.
In response to these challenges, Operation Urban Warrior was born. The intention was to experiment with different ways to work in built-up areas. New camouflage, new techniques, and new technology. Specifically, they tried out military skateboarding.
Okay, so they apparently had a good reason – “maneuvering inside buildings in order to detect tripwires and sniper fire” – but I don’t buy that for a second. I think someone just thought it would be cool to try it out, and somehow got funding to buy an urban combat skateboard. It even had camouflage!
As far as I can tell, the experiment failed, because skateboards never became standard military issue.