Absolutely no one thought Trump would win except for a few very outlier polls . Every major poll for the entirety of the general election showed Clinton with some degree of a lead , the Trump campaign ' s own internal polling didn ' t think he would win , there ' s a reason that Trump ' s win is still being reported as a major upset . That ' s why they were smug , they were dismissive because every single major piece of data showed them ahead , and everyone thought they had it wrapped up . Everyone who had followed the data of the election was in shock on November 9 th , not just the Keepin ' it 1600 guys . Now that it ' s been a few weeks from the election they ' ve gotten back to having really good , and informative episodes imo , their latest interview with DNC Chairman candidate Keith Ellison was great .