As far as the Electro College, and Presidential elections go, Obama is the 44th President. But there have been 56 elections. Remember that many Presidents have been re-elected, and Gerald Ford was never elected, and FDR served 4 terms, etc. So the numbers don't match up.
All elections were decided by the Electoral College. Only four times in U.S. history, the Electoral College system resulted in election of a candidate for President who had received fewer popular votes nationwide than another candidate. And that was a very slight mismatch overall.
Also, the elections of 1800 and 1824 were tied in the Electoral College, so the House of Representatives made the final decision. But overall, it's a pretty fair bet that the popular vote will decide the Presidency. Trump included. (Assuming he is the nominee). At least the odds are in his favor.