Senator Paul established himself as an outspoken Washington outsider. He does not go with the flow of Washington and puts up a fight for what he believes in. Like his father he established himself as one who stands up for liberty and the true meaning of the Constitution. He closely resembles the ideas that his father represented throughout his congressional career.
Rand Paul has been considering a run for President in 2016 and is very likely to run for President. The question is not whether he will run or not, the question is if he was to run would he win the nomination. Right now he is leading the 2016 RCP GOP Primary. Leading right now in the early polls really means nothing. Just ask Rudy Giuliani. Being such an outspoken man in the Republican Party he has made a lot of enemies within the establishment of the Republican Party. Making enemies within the Party can only hurt you. Especially those who control the money flow and outreach in the Republican Party. This can make his path to victory very difficult.
I want to be clear being outspoken is not the problem. I admire those who are outspoken, but being such an outspoken person can hurt his chances in 2016. If we look at the past elections the establishment member of the party is the one that takes the nomination. So if we look at the establishment members of the 2016 field: Mike Huckabee, Jeb Bush, Chris Christie, Paul Ryan, Marco Rubio, and Bobby Jindal. That's not to say these are all the establishment members, just those who are put in majority of the polls.