How’d we get here? My thoughts on how I think it happened:
Hillary's campaign (which I supported full stop and am still heartsick over her loss) had poor messaging. Every commercial was: "Trump said this!" ,"What will our kids think?", "Break that highest glass ceiling", yadda, yadda.
It was about him and her....and not enough about the people. If you wanted detailed proposals, Hillary’s answer was always, "Go to my website". Indeed, she did have detailed proposals that would make any policy wonk proud...but sorry, voters (especially the truly economically anxious ones) wanted/needed to be spoon-fed easy-to-understand solutions, which Trump does expertly (even when they are contradictory lies). Joe Biden has always the perfect ability to speak plainly but with an obvious depth of knowledge...to this day, I regret him not running...but I respect his reasons why.
Yes, Hillary was treated unfairly by the media and Comey (and it looks increasingly like there was Russian interference) but running for President and being president requires — heck, it DEMANDS — a a pugilist.
Trump lives to bloody noses, something I do not think that Hilary or her running mate do not. Hillary hid behind (valid) constant criticisms of Trump, she hid behind ritzy celebrity endorsements, and she hid behind the continuation of Obama's legacy — without ever fully laying out HER plan for these voters with bumper sticker sloganeering.
She could have countered Trump's unspecific blustering with commercials that said, "How is he going to do this...he never says how.”, “What is the GOP plan for Obamacare? They’ve had 7 years to come up with one, but they only vote to take it away” and then follow with, “Here are the bullet points of MY plan, and how I will pay for it without raising the debt.”
I like and respect Tim Kaine, but he also was not the fighter we needed
(̶h̶e̶ ̶d̶i̶d̶n̶'̶t̶ ̶e̶v̶e̶n̶ ̶c̶a̶r̶r̶y̶ ̶h̶i̶s̶ ̶h̶o̶m̶e̶ ̶s̶t̶a̶t̶e̶)̶. I was shocked at how easily Pence gish-galloped past Kaine in the debate. Hillary may have been better served by adding a qualified, strong progressive Latino, like Tom Perez or Xavier Becerra. It might have done more to capture the lightning in a bottle that came with Obama, except this time with the demographically growing and increasingly important Hispanic vote. It could have been an equally important highest glass ceiling to break. Missed opportunity.
Though I personally didn’t like Sanders, adding him to the ticket would have been a smart strategic move. At a minimum, she should have talked up more about how winning the Senate would lead to Sanders becoming budget chair, and how that power would enable him to enact his agenda. Another missed opportunity.
Granted, I live in Texas, where she did not place a lot of campaign ads, so I can't be 100% sure of how her ads played in the areas where she did advertise a lot. ‘Inaugural morning quarterbacking’ is easy (even though I did express some of these same concerns during the campaign).
The Hillary campaign placed too much emphasis on Trump’s temperament, things he said in the past, and his truly deplorable behavior ('deplorable' = another big mistake. Of course we know what she meant, but as the adage goes: “If you’re explaining, you’re losing”).
All of those things were important concerns... but it didn't need to be the only or most important concern. There were not enough attacks on his failed business record, and the failed governance of Mike Pence, his running mate...who Trump already signalled would really be doing the job.
I admit her team was making a lot of their decisions about ad messaging based on polling (that we now see was faulty). Polls that showed that what she was doing was working against Trump. But it didn't work against him. Especially with the legitimately economically anxious voters.
Not because those voters approved of Trump's racism and misogyny...but because his racism and misogyny weren't deal breakers when those numerous character flaws came attached to the impossible promises that he would bring back manufacturing or coal jobs. Hillary didn't made the case strongly enough that he was lying to them, and base it on based his failed business history.
I hate to say all of this. But we have to be honest about where we failed. Because we did fail... and unfortunately, we failed at a time when the stakes were way too high not to.
So, here we are.