The Phlip Side: Lessons from 2016

Election night 2016 was incredibly painful for everyone who fought tooth and nail to defeat Donald Trump.  The only thing saving me from still sucking my thumb from the fetal position is the fact that Florida’s 29 electoral votes weren’t decisive.  We are reminded of the pain from last November every time an outrageous statement or dangerous act comes from our president.  We should lean in to that pain and use it as motivation to go that extra mile when we think that we are too tired to keep fighting the good fight.  That being said, we need to take a hard look at why we lost in 2016 and make course corrections if we hope to be successful in future elections.  While every campaign makes mistakes there is one overriding reason why Democrats snatched defeat out of the jaws of victory again last year: arrogance.

I finished the book Shattered recently, which chronicled the Hillary Clinton Campaign from the inside, and the book both confirmed things I suspected and shed light on other things that made me want bang my head against the wall while muttering, “Why are we so bad at this!”  I give a pass to the Clinton Campaign on a lot of their decisions as I understand that they took what any reasonable campaign professional would think was the best path forward at the time.  There were some very costly decisions/mistakes, though, that they either should have seen coming from a mile away or were completely self-inflicted.  The best campaigns chart out the best strategy they can and executes that strategy to the best of their abilities, but having blind faith in a strategy and arrogantly refusing to verify whether fundamental assumptions that underlay your strategy still hold is political malpractice.

The Clinton Campaign refusing to verify their data models is the most striking unforced error.  They didn’t compare their models to voter contact data, polling, other modeling done by outside data firms, or through any other method.  These methods of verifying data should have been standard operating procedure.  Anyone in the world of political data should use as much data as they can reasonably rely on to make sure that it is all telling the same proverbial story.  I used five different models for the Presidential Election in Florida last year, and when averaged they hit the nail on the head with both the overall result and the fact that Election Day voters were going to be much more conservative than those voters who cast their ballots before Election Day.  This all reminds me of the sage advice by Mark Twain, “It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.”

The arrogance of the Clinton Campaign may have been exceeded only by those on her left that opposed her nomination last year.  This is not a knock again those who supported Bernie Sanders in the primary.  This is a knock against those Bernie supporters who refused to support Hillary in the General Election because she wasn’t “good enough”.  This is a knock against liberals who arrogantly obsess over ideological purity among Democratic candidates to the detriment of getting people elected who will work towards policy goals that they agree with a vast majority of the time.  The Paris Climate Agreement, the balance of the US Supreme Court, gutting Obamacare, and responding to Russia attacking the United States through cyber warfare are just a few examples of how President Trump is different than a President Clinton would have been.  Does anyone still think that Clinton would have been as bad as Trump?

One thing that continues to astonish me is how those on the left who don’t think that candidates like Hillary Clinton are “good enough” never seem humbled by the campaign process.  Campaigns are humbling endeavors, and if they don’t at some point humble you then you are doing it wrong and likely don’t win many elections.  Yet, those who focus the most on ideological purity never seem to be humbled or deterred despite the fact that their approach ends in electoral defeat far more often than not.  The arrogance of the Clinton Campaign and those on the left who never supported her were two of many factors that led to Hillary Clinton losing last November.  As Democrats look forward to making electoral gains here in Florida next year we all need to dramatically dial down the arrogance, come together to support whoever we nominate, and focus on doing the hard work of beating Republicans instead of ourselves.

(Author’s Note: Please feel free to send any comments, suggestions, column ideas, or hate mail to

Sean Phillippi is a Democratic strategist and consultant based in Broward County.  He has worked for campaigns on the federal, state, and local levels, including the Florida Democratic Party and the Democratic Congressional Campaign Committee.  Sean is the Managing Member of TLE Analytics LLC, the political data and consulting firm he founded in 2012.


  1. Ron Baldwin · · Reply

    Let’s not overlook the hubris of how the DNC rigged the nomination of HRC. She only had to get 1,800 elected delegates while Bernie had to get 2,300 elected delegates because the 500 Superdelegates were picked based on pledges to nominate HRC. Despite being a strong backer of Bernie, I held my nose and voted for HRC in the General election.

    1. Hillary won the most votes, the most states, the most delegates, and the most Super Delegates in the primary last year. She won by literally every metric. Blaming the DNC at this point, despite the mistakes that they may have made, is sour grapes. Bernie got beat. Period! He did much better than anyone expected, but he lost because his opponent had more support across the board than he did.

      1. Sean, I was about to congratulate you on a well written and balanced assessment and then you write this drivel. Saying the DNC made mistakes instead of calling out the rigging and favoring done by DWS and her Corporate Cronies is like saying Trump’s efforts at suppressing his tax returns and his ties to the Russians was because he didn’t know any better. When the Establishment Democrats decide to start treating the party like a Democracy instead of a Dictatorship is when we will start winning.

      2. Joe, a rigged election is one where voting totals are tampered with. So, it is a term often misused in a very dangerous way. None of the elections you mentioned were rigged. These things are democracies Joe as the person who gets the most votes wins regardless of who may have supported them. Some elected Democrats did take sides in the Primary Elections, and I have very mixed feelings about that, but there are many instances where elected Democrats back a candidate in a primary with that candidate losing. DWS and Ted Deutch ran against the odds their first times out and won because they got the most votes. There are many more examples like them. Candidates who lose need to focus on what they could have done better instead of crying in their beer and looking for any excuse as to why they lost outside of the obvious one, which is that they simply got beat.

      3. Rigged is exactly right. When Super Delegates are wrapped up by DWS who should have recused herself and worked on her own to support her mentor and then goes on to limit debates, use her position as DNC Chair to undermine Bernie’s campaign totally disregard the DNC charter, that is rigging.

  2. Where to begin?

    You had me until the 4th paragraph, then you veered into the same conventional wisdom and arrogance that doomed the Clinton campaign. You aren’t listening to the voters! When candidates support misguided policies in the name of centrism, compromise, or campaign donations, they turn off the vast majority of those who are eligible to cast ballots.

    People are suffering, they’re angry, and they’re no longer willing to vote for candidates who don’t inspire them, especially when too many Democrats sell them out once they get elected. Candidates who don’t know how to read that desperation will fail.

    I’m reading “Shattered” and it’s obvious that Hillary never made that connection. She sensed it all along, yet never adjusted her campaign. As I read the book, I’m struck by her inability to articulate a message and a reason for running–almost as if her heart was never in it. The campaign seemed more consumed with keeping Biden out, then defeating Bernie, then Trump, than they did with figuring out what the hell was going on with the voters.

    I would be willing to bet that the few people who stayed home or voted 3rd party because of Bernie are heavily outweighed by the people who were inspired by the promises, exaggerations, and showmanship of Donald Trump. Continuing to blame Hillary’s loss on Bernie supporters tells me that you didn’t learn any lessons from 2016.

    1. Hillary got 4.5 million votes in Florida last year. Obama never cracked 4.3 million votes in Florida. You know that I have nothing but love and respect for you Susan, but what you wrote isn’t supported by the facts. If what you claim was actually true Hillary would have gotten fewer, not several hundred thousand more, votes than Obama did.

      1. Hillary Clinton, Patrick Murphy, and Charlie Crist. Three flawed candidates shoved down our throats. Add to that the total incompetence of DWS. I dare anyone to dispute those facts.

      2. If DWS is so incompetent then how did she win re-election by double digits? In her first race DWS ran in a race where the establishment was completely against her, and she won in a landslide because she worked hard to earn as many votes as possible.

        We are on the same side regarding Charlie and the 2014 Primary Election, but I am going to push back a bit Joe. Clinton won Florida by 30 points in the Primary Election, and Murphy won his Primary Election by 40 points. Our nominees are decided by the voters, and in every case you mentioned the voters made their choice and did so in overwhelming fashion.

      3. Re: DWS reelection. She’s popular in her gerrymandered district.

      4. DWS as an incumbent had to spend 4 million to defend her seat. She had Barney Frank, John Lewis, Obama, Biden, and Hillary campaign for her and spent more money on Broward Clubs than in her whole career. She has never emailed and requested money from constituents at the current break neck speed. She is the darling of the Jewish community and yet I see a 2018 upset coming her way. Stay tuned.

  3. My issue with the far-left is that they seem more concerned with purity tests than actually winning. Instead of making an attempt to understand the people they want to represent and learning how to run a winning campaign, all they do is pick fights and throw tantrums whenever they lose – which is a lot. If they have legitimate grievances with the Democratic Party as a whole, I would suggest they step up their game.

    1. You might call it a purity test, but I call it supporting the values of the Democratic Party.

      1. In my experiences, Democratic candidates share many values – the key differences between different candidates is how the candidate presents themselves to the public and how they run their campaigns. Of course, geography matters as well.

      2. Democratic Party voters get to make the decision as to what values they use to decide who to cast their ballot for Susan, so scoffing at the decisions they make is counter-productive. If people don’t like our nominees, then work to nominate someone else. If that person loses though, especially when it isn’t very close, then we need to respect that the voters may not feel the same way that we did in that particular election.

      3. Yes, Sean, Tom Perez thinks we can run the party that way also. How many women did he turn off when he suggested that the party won’t fight for a woman’s freedom to make her own reproductive choices? I suppose women’s rights are negotiable for Democrats. What if we allow Democrats to “grand bargain” away our Social Security and Medicare benefits? Are those earned safety nets also negotiable? I know some racist Democrats, can we let them carry the party banner?

        Democrats have lost because we don’t have a strong set of NON-NEGOTIABLE values that we convey to voters. All we do is confuse them because we’re not clear about what we stand for.

      4. You’re essentially writing off the portion of the Democratic base that actually showed up to vote and elected the candidates you don’t agree 100% with. You’re never going to win if you continue to disrespect those people and refuse to learn from your mistakes when you keep losing.

      5. People are motivated to vote in large part because of a candidate’s perceived strength. In the words of Bill Clinton: “They’ll go for strong and wrong everyday over weak and right.”

      6. So you’re essentially saying that the only reason you vote is because of “perceived strength” of your preferred candidates, rather than their actual stances on the issues? You’re contradicting yourself.

      7. I’m not talking about engaged activists. I’m talking about low-information voters, and/or those who choose not to vote because they aren’t motivated.

      8. First you said the voters care about the issues… and now you’re saying they only care about “perceived strength”?
        To me, that suggests contempt for a majority of the Democratic base. I would never vote for someone who only catered to a small fragment of the Democratic Party while showing contempt for the rest of it.

    2. Hi “Naoya” — long time no see. Can’t wait to chat about Patrick Murphy’s upcoming race.

  4. I’m more concerned with purity tests being applied by the party to the candidates they support. And with purity tests being applied to those who run for office within the party. If you don’t agree with the path being taken and verbalize it, you’re marginalized immediately by people within the party. I think the purity test referenced pertaining to Sanders supporters is a myth. People just want to get back to being for the people, and not corporations and lawyers.It is not the voters who should be taking scrutiny, it is the party and it’s neoliberal stances. But hey, carry on if you enjoy losing elections.

    1. And what makes you any different from them?

      1. What makes me personally different is, I talk to voters without expecting anything from them. I hold my conversations for free. I don’t ask them to pay to attend a gala and conventions at resorts. I talk to people who have worked all day at their fences, on their porches, at the grocery store, at public parks. I don’t take money from anyone. And I don’t ask anyone to give me any. Any expense I have comes straight out of my pocket. People tend to be far more honest when you remove money from the equation.

    2. When we lose as much as we have here in Florida we all need to take a hard look in the mirror and see what we can do better. Our party leaders are elected democratically, so the majority of Democrats who voted in those elections chose the leaders that we have. Further, no one can marginalize you without your consent. There is more than one way to get things done, so if one road is blocked then there is likely several more available if you look for them. I have never been stopped by the Democratic Party in any endeavor that I really cared about.

      1. I agree with you on one sentence. “No one can marginalize you without your consent.” However, that doesn’t mean that they don’t try to do it, and they have. And I have watched people leave the Democratic Party because of that. Also, I am old enough to remember party leaders being more undemocratically elected. I also recall a chairperson admitting to the press that she “keeps Progressives at arm’s length” within her county. The Party slammed the door in people’s faces for far too long. Yes, there is more than one way to do things, and the hard look in the mirror for the party should have taken place long ago, it didn’t. Now we all are paying the price for decisions made by a few. If the continuous election losses in Florida didn’t bring about a hard look in the mirror for the party, nothing will. Both parties are have manipulated voters, elections, laws, rules, primaries, and districts. People follow leaders if they aren’t showing up for you, don’t question them, question your leadership.

  5. ARROGANCE. You got that right. The most arrogant Democrats I know are DWS, Hillary, Crist, Murphy, Reid and Pelosi. Some are gone. The others have got to go.

    1. Joe, I mentioned the arrogance of many in the Democratic Party. I truly believe that every one of the people you mentioned are good people and good Democrats. None are perfect, and a few of made more than their fair share of mistakes. There is more arrogance than there should be in every corner though Joe, even the ones you hang out in my friend.

  6. Sean Atkinson · · Reply

    ” This is a knock against liberals who arrogantly obsess over ideological purity among Democratic candidates to the detriment of getting people elected who will work towards policy goals that they agree with a vast majority of the time. “. I think it is you who has not been humbled by the election results.

  7. Van Jones, a former advisor to Barack Obama, says “The people who ran the Hillary Clinton campaign did not spend their money on white workers, and they did not spend their money on people of color. They spent it on themselves…they took a billion dollars … and set it on fire and called it a campaign…a billion dollars for consultants, a billion dollars for pollsters, a billion dollars for a data operation that was run by data dummies who couldn’t figure out that maybe folks in Michigan needed to be organized…that wasn’t a campaign. It was a boondoggle.”

    I add that the Democrats running the campaign…those advising the media, created polls numbers based on what the public read and heard, were swayed by their own propaganda. And now, the lost election is the fault of someone else. The loss was the work of an international misogynist conspiracy…and my 73 year old wife who refused to consider Hillary Clinton.

  8. TrudyJer · · Reply

    It’s very sad to see people I respect for their passion all seem to remain in their silos. The discussion on this thread is why average people don’t trust either party. The fractured “You didn’t do this right last time attitude is tiresome.” I agree with many points on both sides, BUT we must find a way to reach out to all Democratic leaning voters. That means you need local candidates who speak to the majority in that area. Florida has areas where a progressive stance will never bring in new people. Although I am very progressive on many issues, I can see how many people are completely turned off by others who, for instance, think we should “only push for a single payer healthcare system.” (We’ll be lucky to save any federal healthcare at this point, even parts of Medicare.). Bernie still gives the same unrealistic speeches and his followers (just like Trump supporters) cheer and will not waiver. I love the enthusiasm but I’m pragmatic. Bernie has still not become a Democrat and I want to know why he has not joined the party. Many say he’s co-opted the progressive wing and will break off eventually and form a third party. The mistrust WITHIN the Democratic Party is palpable and this decisiveness will only bring everyone down.

  9. Kate Ellison · · Reply

    The author’s comment, “Our party leaders are elected democratically, so the majority of Democrats who voted in those elections chose the leaders that we have” is just patently false. I am new to inner party politics, but I see very little democracy there. It is all about money and power — the hard work of the party over the years is done by people with the time, money, and connections. It is not a democratic selection process, and to look at elections without the social-political structure around them is really myopic.

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