How to Lose an Election: An Open Letter to Donald Trump

Gregory McKelvey, campaign manager for Sarah Ianaronne, has advice for Number 45. 

By Gregory McKelvey January 20, 2021

Dear Donald Trump, 

You are a man with whom I thought I would never share anything in common. But on the same day—November 3rd, 2020—we both lost elections that had consumed us. For the first time ever in our dissimilar lives, you and I were experiencing the same thing, at the same time: Losing.

I was the Campaign Director for Sarah Iannarone for Portland Mayor. During that campaign, I—along with my staff and my candidate— was tear gassed by both your federal officer and our opponents’ police bureau. We fought hard to get our message out. Our campaign came up just short. It was historic and record-breaking, but we lost. As did you. 

As 8 PM rolled along, I huddled with Iannarone, her daughter, my wife, and my parents and we refreshed the feed to see the results. We were down. You were ahead. But there were more votes to count. I had hope. Hope that our roles would reverse. I called my entire staff in to immediately commence calculations, thinking “just tell me there’s a chance.” But as the clock ticked, it became clear: We lost. I lost. I failed. And I not only failed in my position, but I failed my city. 

Ya, that really hurt. I am sure it hurt for you as battleground state after battleground state was called for Biden. You and me together, Trump, losers both.

While I admit, I struggle to empathize with you, I do empathize with the fact that denial after such immense investment and commitment is natural. But that’s where our paths diverged. I am only 27, I have never held elected office, and four years ago I was just a kid with a megaphone protesting the election you won. But despite the disparity in prestige and power, I really think I could teach you something about how to deal with losing. 

Here’s what not to do:

    • Lie to yourself. You lost dude, by a lot. That’s it. You can throw 1,000 tantrums, you can tell 1,000 lies, you can send 1,000 tweets—oh wait. Anyways, you still lost. 
    • Publicly deny the result of the election. I know that feeling of denial. That feeling of: “This can’t be real.” But here’s the thing, Ex-President Trump, it is real. And that’s how democracy works. Someone wins and someone loses. It does not matter if you felt it was unfair. 
    • Use the courts to advance baseless claims. Our judicial system, while often flawed, should not be made a mockery of, especially by the President of the United States. Our opponent, Mayor Ted Wheeler, broke campaign finance regulations like he was addicted to it. He was supported by a million-dollar Super PAC of establishment interests that were impossible for us to combat. We had legitimate complaints about the fairness of the election. But that was the election. You cannot complain that the basketball hoop was ten feet tall after you played all four quarters, or even in Dame Time. 
    • Blame everyone else for your loss. When you lose an election it usually means you just got fewer votes (not counting 2016, and let’s not talk about 2000 either). But regardless, it is pretty simple math. Is this number higher than that number? That’s why you lost. You got fewer votes. You got fewer electoral votes. Maybe your campaign strategy was bad, or maybe you are unwanted. Regardless, that’s on you, bro. 
    • Incite an insurrection to overthrow the legitimately elected government of The United States. This one should go without saying, but you really should not have done that. 

And here’s what you should do:

    • Accept it. It’s okay. I know it is hard to overcome toxic masculinity, which inclines you to believe men—specifically you—should only win and win bigly. But losing is part of life. Refusing to admit defeat is not manly, it’s just sad. Reflect on why you lost. I can help with this. In your case, you lost because you are a racist pig. In my case, I made some mistakes that I have admitted and am aware of, including underestimating both the role misogyny would play in the race and how much the establishment would unify.  We both had something to think about. 
    • Work Harder. You seem lazy, man. Watching cable news is not leadership. You aren’t going to win like that. The only work you seemed to do was spread COVID-19 around the country. You even killed Herman Cain. That’s one less vote!
    • Use your loss to fix what you think is wrong. Stacey Abrams lost a race due to voter disenfranchisement. So what did she do? She got to work registering voters and saving our Republic. Sarah Iannarone lost in part because of a lack of voting reform or enforcement of campaign finance violations and she's already working to address these issues. You seem to be very enamored by voter fraud—maybe you could spend your time finding all, what, three of the examples of voter fraud and help these often confused voters clear up their voter registrations. 
    • Reach out to those who didn’t support you and work to understand where they’re coming from. I have been trying to extend an olive branch to our campaign’s electoral opponents and their supporters to figure out how we can move Portland forward together. If you really believe in making America great, work with the Biden administration to correct the evils you have perpetuated, and do it as quickly as possible

In short, there is no shame in losing. While I know it hurts, you aren’t acting like an adult—my toddlers would get a timeout for behaving like you. From one random 27-year-old to a now-former president, it’s time to grow up: losing is a crucial part of life. Michael Jordan played six seasons before winning an NBA Championship. Damian Lillard played eight seasons before surely winning his first championship. Even Muhammad Ali had five losses in his career. Each loss is an opportunity to learn, to be better, to evolve. 

Here’s the thing, Donald: we progressives lose a lot. A lot. But we keep fighting. We keep organizing. We learn from it. When we lose, we do the work to win next time. And if not next time then the time after that. You wanted to Make America Great Again, but you forgot that while America has a dark past we always continue to progress. For those whose marriage was illegal six years ago until marriage equality, we have progressed. For those whose marriage was illegal 60 years ago, like my interracial parents, we have progressed. Four years ago things like universal income, healthcare for all, and even Black Lives Matter were all controversial terms. And all that progress took decades of work, not whining. You and your supporters have thrown a massive cumulative tantrum during your loss. But you really have got to get used to losing. We are going to move on without you, and be better off for it. 

Seeing as how you are suspended across the internet, you can send your response to the address to which you were supposed to send the stimulus.


Gregory Robert McKelvey

P.S. Black Lives Matter.

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