Can man be free without having possessions? There's a distinct theory that all liberties derive from property, example: I own myself -> I have right to my life, my thought, and the products of my actions. Sorry if this is the political aspect of "freedom"
You'd have to define "free" before I respond to this. Apparently the question is about happiness not about freedom.
Happiness is a tricky thing to consider because it might be happiness for a minute/hour/day (hey, you could do some drug and be happy for all that time even if you don't eat, you are naked and don't own anything)
If you want to be happy for a longer period you need basic things like: food, cloths, shelter, human company -- all of these require some kind of possession. But this "need" is somehow relative, since "content" is a state of mind it can be controlled by mind and it doesn't require too many things: for example ascetic monks. One could be "enlightened" and do it without cloths or without human company but it's not something common (and even those need food and a kind of shelter and a guarantee that nobody would take their only possession: life) and it's not something that I'm willing to try, I'm pretty content living in the material world.
The only question is: would
you be happy without having possession? Leave your wallet at home and try sleeping and living on the street for a week and then respond.
EDIT: and that trasforms into the discussion that we already had in another thread money vs. happiness, I don't think I have anything to add about that