Because not enough reporters, columnists and editors asked themselves that question, the country is now being blackjacked by a Trump candidacy that will change America, whether he wins or loses.
In most newsrooms, the first announcement of a Trump candidacy led to jokes about comb-overs and casinos.
And there it lay, while the news people, used to the incumbents and the expected candidates, went back to the safe little press conferences and the pre-chewed press releases, while around us rose a howl of discontent that could not be heard through the brick walls of the newspaper building, could not penetrate the soundproof safety of the broadcast studio.
We missed the story. We walked right past every blaze of middle and working class anger that heated up the Trump campaign. We couldn't even smell the smoke. House fires we could cover, but we missed the flames that engulfed a nation.
We blew it. Trump talked to crowds of people who are afraid they'll lose their guns, afraid there will be Sharia in Alabama, angry because the plant closed but the welfare people kept their checks.
Read the "think pieces" newspapers have done about Trump in the last few months. How many of those articles explained patiently why Trump was going to lose or why he should lose? The articles are wishes, desperate notes to God begging him to strike down Donald Trump.
I've been a full-time newspaper employee for 33 years, more than half my life, and I have never been as ashamed of my business as I am right now.
We decided Trump had no chance. We decided Trump would fade after the first primary. We decided his supporters were too dimwitted to count.
If America's mainstream media could have abandoned its anti-working class bigotry for a second, we would have taken Trump seriously from the first day. We would have ripped into his finances, his personal life and his associations. We would not have done a hatchet job on him, but would have found out who he was and how he worked and what he wanted. We would have done our job on its most basic level.
Instead, we told the jokes and we relentlessly ignored the people we regard as fat-bellied NASCAR fans who buy the paper but are secretly despised by the people who write what's in the paper.
By the time we remembered that people we look down on could vote it was too damn late. We hadn't done our jobs.
We're reporters. We can duck under the crime scene tape. We can get the senator on the phone. We stand in the front, but we come and go through the back door, avoiding the crowd. We joke with the incumbents, little private jokes. We know who is going to get the nomination. We know who is going to win.
This time we were wrong, and we were wrong because we failed to ask ourselves, "Who cares what I think about Trump? What do other people think?"
To find out more about Marc Munroe Dion and read features by other Creators Syndicate writers and cartoonists, visit www.creators.com. Dion's latest book, "Marc Dion: Vol. I" is a collection of his Pultizer Prize-nominated 2014 columns. It is available for Nook and Kindle.
Photo credit: Michael Coghlan