Actually, it happens quite often. What seldom happens is the loser actually being able to PAY the amount the court awards.
There was a recent case where a couple of individuals who happened to work for a gun control group sued a gunshop over the sale of a weapon used in a nutcase's shooting spree.
The individuals sued because they had standing to do so, where the gun control group did not. While it was never publicly stated we all believed the gun control group agreed to cover their costs.
THEY LOST. AND, the court said they had to pay all the legal costs of the gunshop, as well as their own. Last heard from, the couple was begging for money and filing bankruptcy because apparently the gun control group didn't help them with the costs, and they didn't have the money to meet their court ordered obligations!