Silver, who rose to fame during the 2008 presidential election, had as late as January this year put the likelihood of Trump winning the nomination in the low single digits.
He would later admit that he "acted like a pundit screwed up".
By late last month, FiveThirtyEight's prediction models had given the Cubs a 24 per cent chance versus 76 per cent for the Indians - exactly the same odds it gave to Trump.
The Cubs' historic win, which was almost predicted by Back to the Future, may have moved Bill Murray to tears, but Trump supporters - many of whom dislike Silver, to say the least - were equally joyful.
"IT'S HAPPENING," tweeted @KGBVeteran. "Nate has the monkey paw version of future sight. It always shows him what he DOESN'T want to see, and it comes true," said @TheHippestHippo.
"This might be the first accurate prediction of the year for you, Nate Aluminum," tweeted @comicsea44. "Apparently you used all your prediction powers on one single tweet this year," @hunterswogg said.
What makes this whole thing even spookier? Joe and Marlene Ricketts, the family that owns the Chicago Cubs, donated $US1 million to Trump's campaign less than two months ago.
But as far as predictions go, no one can beat this guy:
