Trump didn't get lucky he campaigned smarter. He won the working class white votes which won him those pivotal states. Hillary may have won the popular vote but only succeeded in consolidating the base.
It's also funny how those same democrats who were up in arms about tEh PoPuLaR VoTe are happy to go to a brokered convention if Bernie gets the most delegates but not enough to lock in the nomination.
Clinton spent $1.8 Billion dollars in 2016 compared to Trump's $980 Million dollars. Hillary found out money can't buy you happiness after all. Trumps expenditure was the lowest since John McCain in 2008. He had to campaign in a more targeted and smarter manner with his lesser resources and he pulled it off against all odds.
Bloomberg has already spent $600 Million dollars on his unconvincing run at the top job and with $100 Billion behind him is likely to throw much more money at it before November. Money is everything at the beginning of a presidential race but at the end it doesn't guarantee a win unfortunately.