Could a Boricua President be Eligible?

I learned something a few weeks back that got me thinking...

I didn't know that people born in Puerto Rico were automatically citizens of the United States upon birth, as per legislation that Pres. Teddy Roosevelt had signed. That makes sense, in its historical context, and makes sense today, seeing as how Puerto Rico is still a territory of the US while enjoying some autonomy.

But that got me thinking...This past election year had some debate (obviously in the early goings) about the candidacy of John McCain, since he was born on a naval base in the canal region of Panama. Since he was a Republican (this is my educated guess), the media gave him a pass and asked some right-friendly scholars to weigh in, and they said that an American naval base anywhere in the world is considered American soil, so his birthplace shall not be questioned. Fair enough (unless you're Obama and fighting a ridiculous battle against anti-US jackasses convinced he was born in Kenya), naval base soil shall work, unquestioningly.

Another piece of this topic is Barry Goldwater. He ran for presidency against LBJ and lost due to a successful campaign that he'd nuke Vietnam (he probably would have). But Barry Goldwater, Republican candidate for the presidency, was born in Arizona. So what, you may ask? This was the territory of Arizona, and not the state of Arizona. His candidacy was never fought along the lines that he was ineligible due to his birthplace.

He was born in a US territory and was apparently successful in gaining his party's nomination.

So my thought, or my question, is: Is it possible for someone born in Puerto Rico to win the election for the office of President, and actually be eligible to hold the position?

I'd imagine, if it'd ever come to that, that if the possible candidate was a hard-liner against Hugo's and Raul's regimes, then, like McCain and Goldwater he'd get a media pass, and be championed like Obama. And, if the candidate had a progressive social plan, like, say Evo Morales or somebody similar, and they appealed to intellectuals rather than business interests, the media would howl with indignation, and every attempt to foil their pursuit would be made, probably starting with an attitude of "they're not even eligible"...

What other expectations would you have for a system where business controls the media?