Do you get the health benefits of olive oil by ...

Yes, but you have to eat a heck of a lot of olives... Seriously though, an olive contains - on top of oil - some water, carbs and a lot of fiber (cellulose), not to mention the pit. To get the amount of olive oil that equals one tablespoon a day, you'd have to consume about two pounds of olives daily (!). The trouble with olives however is that you don’t eat them raw – they have to be pickled or cooked. Cooking destroys some of the essential fatty acids in the oil, while pickling adds enormous amounts of salt, which kind of defies the purpose of taking in olive oil to begin with (one lower your blood pressure whereas the other one raises it).