There were 14 presidents who never served: - John Adams - Thomas Jefferson - John Quincy Adams - Martin Van Buren - Millard Fillmore - Grover Cleveland -

There were 14 presidents who never served: - John Adams - Thomas Jefferson - John Quincy Adams - Martin Van Buren - Millard Fillmore - Grover Cleveland - William Howard Taft - Woodrow Wilson - Warren G. Harding - Calvin Coolidge - Herbert Hoover - Franklin D. Roosevelt - Bill Clinton - Barack Obama And then 6 with the least amount of experience entering office: - Ulysses S. Grant - Grover Cleveland - Woodrow Wilson - Dwight Eisenhower - Barack Obama - Donald J. Trump You'll notice there were three on each list - Wilson, Cleveland and Obama. I'll let you decide on the merits of their administrations and how successful they were. Either way, your experience and military service are not clear indicators of how successful you'll be as a president. Harding, Wilson and Grant regularly make the list of the worst, while several non-military types like Clinton and Obama were two term presidents. Eisenhower is generally (no pun intended) regarded as a great president as well. Don't forget the founding fathers Jefferson and Adams are both seen as revolutionary hero's. Honestly when you look back, it's a crap shoot. EDIT: You forgot to mention that Trump did oversee over 500 business entities that were valued at north of $4 billion. His organization has interests in real estate development, investing, brokerage, sales and marketing, and property management. The company owns, operates, invests, and develops residential real estate, hotels, resorts, residential towers, and golf courses in different countries.