Yes, Trump's win may be the biggest surprise of 2016. No one believed Trump would stay in the race to begin with. Then, everyone was sure he'd lose the primary election. For many of us, we just couldn't believe there was any way a man like Donald Trump could possibly be elected president.
Even a few hours into the election returns, people thought that Clinton was still going to win. Clinton and all of her supporters were very sure that she was going to win. Slowly, as the night went on, the media began to realize that Trump was about to win, exactly as he predicted.
Trump winning Time's Person of the Year was perhaps the least surprise of 2016. He was obviously going to be chosen, if the history of Time's process continued as it has for decades. He won being chosen for the cover because he was the most influential, yet controversial person in 2016, and that cannot be disputed. Trump was able to get the Nation's and the World's undivided attention in 2016, and for better or for worse, that gave him the win for Person of the Year. Time magazine's choice was not a surprise whatsoever. It would have been a surprise if he had not been chosen.
No, Donald Trump's election to the presidency was not the year's biggest surprise. Considering the widespread contempt that American people have for both the Democratic and Republican Parties, it is not surprising that a candidate who ran on a populist and anti-establishment platform was elected. In the absence of the option of choosing progressive populism like Bernie Sanders offered, the people chose authoritarian populism over the corrupt establishment represented by Hillary Clinton.