How Could Trump Have Possibly Won?

Full disclosure: I supported Hillary Clinton in the 2016 primary and in the 2016 general election.

I've been debating if it's too soon to do my postmortem on this election. People are protesting, they're questioning, they're WTFing their friends, family, and neighbors who voted for Trump, they're angry and upset. I get that. I'm angry and disappointed every time I turn on the TV and see something about Trump and his circus of a transition team trying to get him ready to be president. I've accepted that he won and Hillary lost, but I'm still upset about it. So I've been trying to make my peace with it, namely by starting this blog and doing a deep dive into issues that I feel are important and saying things that I feel need to be said.

If you're still in mourning, and you feel you're not ready, I understand. But you might not want to read any further. In trying to flesh out what I think went wrong, I'm going to point out what I deem were fatal flaws with Hillary's campaign and its strategies and with Hillary herself.

First, let me say that I think Hillary Clinton is brilliant in every sense of the word. She is without a doubt, the smartest and most capable woman politician in our era. She has been the subject of vicious personal attacks, but she has always prevailed and lived to fight another day. And make no mistake, Hillary is a fighter who never quits just because things are hard.

Unfortunately, the sins of the past (not necessarily hers) have followed her for almost 25 years. Bill's indiscretions and nearly a dozen other mostly unfounded investigations against her and Bill cast a dark cloud over both of them. Never being one to sit on the sidelines, Hillary moved to New York and won a Senate seat. She was moving on and moving up, trying to leave the ugly past behind.

In her first run for president in 2008, Hillary fought hard and had some great success in the primary, but there were still some trust and likability issues surrounding her, and the enthusiasm for Obama catapulted him to the nomination and the presidency. Hillary thrived as Secretary of State, but she left wounded and vulnerable because of the ridiculous, endless, and fruitless Benghazi hearings, and the ultimate revelation of her private server. A private email account may not have been so bad, but this was a private server. Not good. At all. A public servant who sets up a private server for official and private email leads people to believe there's something to hide. After being accusing of muddling the handling of Benghazi to point of negligence, she really didn't need another bull's-eye on her back.

With all the baggage hanging around her neck for 25 years, all the scandals and non-scandals, Benghazi, and now the private server, she still decided to run for president in 2016. Even before the general election, even before the primaries, there were times when I questioned the conventional wisdom of her decision. Hillary's likability and trustworthiness were once again becoming major issues for her. I wondered at the time if it would have been better for herself and for the party to acknowledge her vulnerabilities and pass the torch. We would have thanked her for long years of public service, sought her counsel and experience, and moved on.

Although I did admire her courage for being willing to subject herself to the abuse that she would most certainly encounter during the campaign, I feared the ugliness of it -- both professional and personal. But running for president isn't for ninnies, and Hillary is an iron lady. So I really wanted more than anything for Hillary to stick it to the haters...run for president, get the nomination, and win the presidency. Despite the scandals and the unforced errors, she worked incredibly hard for it and had damn well earned it! But the scandals and the mistakes would ultimately prove to be insurmountable.

Bernie Sanders' quick rise to national-level celebrity was fueled by a fiery populist message that really seemed to resonate with the unemployed, the working poor, the working class, college students, and just about everyone in between. He ran against Washington elites, Wall Street, money-grubbing corporations, and job-killing trade deals. He also successfully tied Hillary to all of those things -- effectively authoring what would be some of Trump's best attack lines against her in the general election. Meanwhile, Donald Trump was stepping all over himself, hurling insults and bigotry, and being completely written off by the media, the GOP, and his fellow Republican candidates.

On March 8th, Bernie stunned the Clinton campaign by winning the Michigan primary by just over 1 percent. That might not seem like much, but looking at the sheer number of counties that went for Bernie, it changes the perspective a bit. And what really shocked Team Clinton was that she was leading in the polls by double digits heading into the primary.

Hillary won Ohio on March 15th by 13 percent, so I'm sure that softened the blow from losing Michigan. However, on April 15th, Bernie obliterated Hillary in Wisconsin, winning by more than 13 percent and every single county except Milwaukee -- and Hillary only won that by 3 percent. The polls had been closer in Wisconsin, but Sanders had an average lead of four to five points.

Hillary went on to win Pennsylvania by about 12 percent and the overall primary by 13 percent. But those losses in Michigan and Wisconsin should have been a wake-up call for Team Clinton. Her strategists should have immediately been asking "What was in his message that really resonated with people?" "What was in Hillary's message that didn't?" "What voting bloc did he appeal to?" "What voting bloc did Hillary not appeal to?"

Not only did the Clinton campaign not ask those questions, but it didn't bother to spend any real time in those states talking to the voters after the primaries. I know, generally you don't spend your money or political capital in "safe" states. But who the hell assumed these were safe states to begin with? Oh, I remember...it was the polls. They're never wrong. Remember the Michigan primary? Regardless, it seems that Hillary and her people thought nothing had changed across the country in 4 years and therefore didn't bother to do anything more than copy/paste the Obama campaign operation from 2012 with no tweaking, updating, or research. A huge underestimation on the part of the Hillary campaign was that even though Obama saved the automotive industry, he couldn't save everyone in its wake of its near-collapse. People in the Rust Belt were still hurting and not thriving as they hoped they would. And through all of the achievements and successes of the Obama Presidency, some people got left behind. Bernie had spoken to those people and acknowledged their plight. He pledged to fix the system, end these crappy trade deals, bring back jobs, and make college and health care more affordable for everyone. Hillary tried to incorporate that same populist message, but it fell flat, especially when she didn't make much effort to deliver that message in person.

The more obvious it became that Trump would be the Republican nominee, the more complacent the Hillary campaign seemed to become. Trump's own primary rivals called him the chaos candidate, a con man, and a pathological liar. The more that came out about Trump (and out of his own mouth), the more emboldened the Hillary campaign became. In their eyes, he was destined to fail and die by his own hand. After the Republican Convention, Trump racked up so many self-inflicted wounds that the media couldn't keep up anymore. It became a joke and so did Trump. But there was this one little thing...

In between his tweets and public comments calling Bernie Sanders a sell-out for supporting Hillary at the Democratic Convention, Trump tweeted on 25 July, "Sad to watch Bernie Sanders abandon his revolution. We welcome all voters who want to fix our rigged system and bring back our jobs." He repeated it publicly several more times. I remember watching the talking heads write off Trump's sentiment as self-serving and ridiculous, and it was ultimately ignored and forgotten. It turned out to be a not-so-subtle shot across Team Clinton's bow, and here's why: Bernie is a progressive socialist, and Hillary is a moderate capitalist. How do you bridge the divide to unite the party? Pull Hillary to the left and risk alienating moderate voters? Keep Hillary in the center and risk alienating the enthusiastic Bernie supporters who went nuts for him but were cool to her? What to do, what to do. Hillary decided to lean more left and adopt most of Bernie's agenda. The problem was, the voters weren't buying it. They knew who and what Hillary was, and she wasn't fooling anybody. Additionally, there was a growing perception and anger that Hillary, the Washington insider, was the DNC's anointed one and that the system was rigged against Bernie Sanders.

Regardless, Team Clinton remained confident and started making headway into traditional battleground states, leaving the always-reliable Blue Wall in the rear-view mirror. But again, how safe was that wall? After losing Michigan and Wisconsin to Bernie in the primaries, Hillary went to Detroit once and made no return trips to Michigan or Wisconsin until days before the election. Donald Trump went to Michigan five times between the Republican Convention and 7 October. He also went to Wisconsin five times between the Convention and 1 November. I lost count how many times he went to Ohio and Pennsylvania. Guess who was out there talking to those voters? Not Hillary. She seemed to take those reliably Democratic voters for granted. And most unfortunately, Trump was able to fill the void that Hillary left. He filled it with a lot of crap he can't possibly deliver, but at least someone was listening to the voters and telling them exactly what they wanted and needed to hear.

Most shocking to me was when Hillary was really high in the national and statewide polls, the Clinton campaign started eye-balling Arizona, Texas, and Georgia as potential battlegrounds. Can you imagine how much that must have pissed off Rust Belt democratic and independent voters that maybe weren't that thrilled about voting for Trump but would have died of old age waiting for Hillary to come and talk to them? It's almost cringe-worthy that Team Clinton listed all the states she could lose (the ones she spent the most time in) as long as the Blue Wall held (states in which she spent almost no time until the very end). The campaign even made its peace with potentially losing Ohio, which Obama won twice. Again, the voters in those states were left out in the cold. Hillary and her campaign insisted repeatedly that there was no time for complacency and that they weren't taking anything for granted. If they had embraced and addressed the concerns of one of their core voting blocs, the Rust Belt working class, those voters wouldn't have been left vulnerable to Trump's sideshow sales pitch. And don't think that the "basket of deplorables" comment was forgiven or forgotten. That hurt her more than many are willing to acknowledge, in much the same way Mitt Romney's 47 percent comment hurt him.

Most of us thought there was no way the qualified, experienced, tested, eloquent Hillary Clinton could possibly lose to a vile, temperamental, misogynistic, race-baiting bigot who wouldn't release his tax returns, engaged in questionable business practices that screwed small-business owners and bankrupted his own companies, had inexplicable adoration for Vladimir Putin, and demonstrated ignorance of all things presidential at every turn. To add more insult to his self-inflicted injuries, Hillary crushed him in three debates, making him appear even less prepared for the presidency.

The voters either overlooked or forgave Trump for his crudeness and extremism because other things he said and believed were more important to them -- dysfunctional Washington, Obamacare, trade deals that cost Americans their jobs, terrorism on American soil, and out-of-control illegal immigration. And they seemed to love not only that he addressed these things but that he was not a Washington insider owned by constituents and lobbyists. The voters were sick of Washington and everything it meant to be an insider and a Beltway veteran. Yes, they sent almost all the same House and Senate candidates back to their jobs, but a majority of these voters blamed Obama for their problems and not Congress. Counties in Pennsylvania, Ohio, Michigan, and Wisconsin that voted twice for Obama flipped for Trump. It happened in counties in Florida and Virginia too.

Hillary could not shake her status as a Washington insider, her coziness with Wall Street, her repeated attempts to double-talk her use of a private server, the suspicion of a pay-for-play operation while she was Secretary of State, the lingering Benghazi stench, the cursed WikiLeaks revelations, and on and on. Four more years of an Obama-like administration and the threat of countless more investigations and impeachment hearings and fights over Supreme Court nominees grid locking all other business in Washington didn't help her either. Some of these characterizations were from self-inflicted wounds, and some were due to circumstances beyond her control and thereby wholly unfair. But her biggest mistake was riding a wave of confidence while leaving a core voting bloc wide open for a Trump infiltration. And yes, she's still ahead in the popular vote, but she blew an early and solid advantage in the Electoral College by not shoring up what had been a solid Democratic base.

To all the talking heads and Clinton campaign strategists who kept asking "What the hell is Trump doing in the Rust Belt?" I hope you get it now. And shame on all of you for writing off Michael Moore's insightful article explaining how, where, and why Trump would win big and win the presidency. Perhaps the lean-red momentum in Wisconsin, Michigan, Ohio, and Pennsylvania was too great to stop and reverse. But leaving those states in the lurch was a bad move.

I'm not sure which Democratic candidate, if any, could have beaten Donald Trump. Obama's approval numbers were over 50 percent, but that depended on who you asked and where. Bernie might have had a shot, but who knows. I feel bad for Hillary and I wish her well. We are in no way, shape, or form better off with Donald Trump, but I can't help but feel that a less-wounded candidate may have prevented Trump's ascent.