Winning in 2020 Means Knowing Who Can Reach and How (and Ignoring Who We Can’t)

It’s hard for many of us to understand how Donald Trump earns a positive job approval from over 40% of Americans. If a Democrat had doubled the deficit, alienated allies, groveled to foes, lied, and evaded accountability like Trump, we know how that same 40% would feel.

So, how do people who claim to want fiscal responsibility support someone who shows none? Or Evangelicals support a man so evidently immoral? Or people who demand an America that works for “real Americans” support a man who’s taken from the middle class to give to the wealthy?

These aren’t idle questions. We must understand this to win in 2020. Those of us on the left cannot reach every Trump supporter, but we can earn the trust and votes from enough to win. Here are four categories of Trumpsters I believe that we on the left can win and four we can’t:


What They Mean: They actually see a lot of Trump faults, but Trump’s been good for their wallet and that’s what matters to them.

What They Get Right: Stock market’s up, unemployment’s down.

How To Reach Them:

  1. Stock markets aren’t the economy; many Americans aren’t benefiting
  2. Economic cycles are inevitable; Trump’s actions will worsen the downturn
  3. The past is past; what do we need NOW for future economic success?

How NOT to reach them:

  1. Trump’s just extended Obama’s expansion. True, but that’s ancient history to someone watching their 401k increase.
  2. Trump profits from the office and wastes tax dollars on golf trips: True, but the selfish don’t care provided they profit.


What They Mean: Trump/GOP cares about my job, while Dems are devoted to helping everyone else but “hard-working real Americans.”

What They Get Right: Trump’s policies created some job winners (but also some losers)

How To Reach Them:

  1. Steel, coal, and farm labor is steady/down. Layoffs continue.
  2. Global demand/tech is changing — workers need support/training.
  3. Dems will always be social progressives, but to win in 2020 they must prioritize messaging on how their policies help working Americans.

How NOT to reach them: Do not

  1. Blame them for failing to see reality or keep skills updated.
  2. Suggest some group “deserves” economic anxiety for voting as they have.
  3. Embrace simplistic answers: Learning to code is not a reasonable, scalable answer.


What They Mean: Either 1) FOX News has convinced them of something demonstrably untrue or 2) they really just hate taxes

What They Get Right: The GOP does lower taxes.

How To Reach Them:

  1. The informed are already turning on Trump; amplify their voices.
  2. Fight lies — share data on Trump’s deficit and how US taxes compare to Western nations.
  3. Appeal to patriotism/care for children: We must start paying our fair share.

How NOT to Reach Them:

  1. They’re uninformed — educate them, don’t insult them.
  2. We can’t balance the budget only by reducing discretionary spending. We must have an honest discussion of how new taxes are required.
  3. What’s “fair” is subjective. Focus on what’s needed and best for the US, not what’s “fair” for one group or another.


What They Mean: Either 1) they think Dems don’t share their values, or 2) This is cover for the fact they’re part of an unreachable group (see below)

What They Get Right: Trump panders to this group in ways Dems won’t

How to Reach Them:

  1. Many Evangelicals HATE Trump. Amplify their voices.
  2. Calmly promote Trump’s immorality and invite these folks to reveal what REALLY matters to them.
  3. Keep the focus His word and teachings: “As you did to the least of my brothers…”

How NOT to Reach Them:

  1. Do not mock their faith or religion.
  2. Don’t deride GOP policies; promote how Dem policies align with His guidance, lessons, and word.
  3. If someone reveals they’re a member of an unreachable group (below), stop. Agree to disagree. End the dialog. Block if needed.


THE UNREACHABLES include 4 groups:

  1. GOP true believers: FOX News is on a non-stop loop. Their belief is akin to religious fervor: Dems are evil, immoral, hateful and dangerous. They may embrace a better GOP candidate, but not a Dem. Leave them to the Lincoln Project.
  2. Bigots: Racists, sexists, homophobes, xenophobes, and religious bigots. They’ve always existed, and sadly they always will. Some are smart enough to hide it; some aren’t. They enrage us, bait us, troll us, and the best we can do is ignore, report and block.
  3. Gun nuts: They’re right — Dems will pass laws regulating guns. Some actually want sensible gun laws, which is why the GOP is weakening with this group, but hard-core gun advocates who believe they need assault weapons to defend against government overreach or to protect their families are lost to us on the left.
  4. Social regressives: Some just truly believe sin, sexual freedom, abortion rights, gay marriage, and the like hurt the US. It’s tough for some of us to accept, but it’s their right to believe this. We’ll never convince them, so let them believe what they want, leave them alone, and focus where we can influence votes.

In 2020, how much of your time will go to arguing with people you cannot change? How often will discussions devolve into ad hominem attacks? What do we need to win? Remember that in 2016, Hillary won the popular vote and would’ve done the Electoral College with just 80,000 more votes in key battleground states.

An army doesn’t win by fighting returning fire at their foe’s every feint. In 2020, you’re in an army for good. Waste your time on anonymous foreign agents, bots and unreachables, and we’ll repeat 2016’s outcome. Alienate those we should reach, and we’ll repeat 2016’s outcome.

Our enemy isn’t people. It isn’t even Trump. It’s ignorance, misinformation, and propaganda. It’s untruthful microtargeted ads on Facebook (which should care but doesn’t). It’s hidden motives, dark money, and foreign influence.

We on the left have right on our side. We care about people. We care about equity, fairness, and prosperity for all. Our policies help working Americans and are good for the economy.

Fight fair, honestly and with facts. And don’t waste one tweet, post, breath or moment on those who won’t do the same.

Personally, a politically-engaged progressive. Professionally, a Vice President Analyst of Customer Experience at Gartner. Opinions expressed here are my own.