If it ever was alowed to be free.
I don't know if it ever was.
But think of it like a continuum, with absolute tyranny on one side, and absolute freedom on the other. There are times that have been closer to the freedom end than others, and there is a direct relationship between those times and the prosperity of the people.
Where exactly? The U.S., Europe, Africa? I think Somalia pretty much has a completely free market right now. (correct me if i am wrong)
There is no central government, no regulations, no taxes. "Legal" matters are decided by the clans and people who commit murder/theft/whatever are thrown out of their respected clans and from then on considered outlaws, which means that they will receive no protection from anyone and are at the mercy of the public.
No, Somalia's government is very oppressive where it's oppressive. Just try setting up a land-line phone service there and you'll see.
This is where I got most of this stuff btw: http://fringeelements.ning.com/video/stateless-in-somalia