10 Most Enraging, Cringeworthy — AND Awesome — Moments From Trump’s Staged DoorDash Press Event

President Donald Trump’s staged DoorDash press event was so chock full of enraging, cringeworthy, outrageous — and even awesome — moments that it’s hard to narrow them down. But here are ten of them.

“DoorDash Grandma” Sharon Simmons participated in a photo op on Monday in which she delivered McDonald’s food to Trump and extolled the “No Tax on Tips” provision that was part of Trump’s signature “Big Beautiful Bill” legislation. The event morphed into one of the more bizarre press Q&A sessions on record — quite an accomplishment in the Trump era.

Simmons also spoke to reporters on the North Lawn minutes after the photo op, and has been a longtime advocate for the “No Tax on Tips” policy, testifying last year at a field hearing in support of the provision.

Before I get to the rest of the list, I want to begin by listing my first “awesome” moment.

AWESOME: Sharon Simmons

DoorDash Grandma earned awesomeness several times, but I want to start off by noting that whatever the cringe or outrageous or weird or enraging aspects of this spectacle, Simmons bears no blame for any of them. She’s advocating for something that’s helping her family and capitalizing on powerful people who want to reward her for her advocacy.

CRINGE: The Whole Thing But Especially When Trump Breaks Character

Simmons and Trump start out sticking to the script, with Trump greeting her in local commercial acing mode by saying “Hello. Nice to see you.”

But as Simmons plays along, Trump looks out at the gathered press and says “This doesn’t look staged, does it?”

ENRAGING AND CRINGE: Trump Ropes DoorDash Grandma Into Gaggle By Attacking Press

Simmons, as she would end up doing repeatedly, politely grits her teeth and bears it while trying to keep from being sucked in:

PRESIDENT DONALD TRUMP: Well, you’re really nice. Would you like to do a little news conference with me? These are not the nicest people. They’re not nice like you, you know that, right?

DOORDASH GRANDMA SHARON SIMMONS: I’ll do whatever you ask me to do, sir.

ENRAGING AND CRINGE: Trump Ropes DoorDash Grandma’s Husband’s Cancer In For His Lie About Jesus Post

The president sparked anger among MAGA figures and others with a now-deleted post depicting himself as Jesus. When Trump was asked about it, he made up the absurd lie that he thought it was a “doctor” meme — then tried to draw Simmons in by referencing her husband’s cancer diagnosis:

REPORTER: Mr. President, did you post that picture of yourself depicted as Jesus Christ–?

PRESIDENT DONALD TRUMP: Well, it wasn’t a depiction. It was me. I did post it, and I thought it was me as a doctor, and had to do with Red Cross as a Red Cross worker there, which we support.

And uh– only the fake news could come up with that one. So I had… I just heard about it and I said, “How did they come up with that?”.

It’s supposed to be me as a doctor making people better, and I do make people better. I make people a lot better.

As an example, the 11,000, I understand your husband’s going through a treatment.

DOORDASH GRANDMA SHARON SIMMONS: Yes, sir, yes, sir.

PRESIDENT DONALD TRUMP: Going through some very serious cancer treatment, so this goes a long way.

DOORDASH GRANDMA SHARON SIMMONS: Yes, sir, it sure does.

ENRAGING: Not One Reporter Followed Up On That Absurd Lie

Trump hung around for fifteen minutes, and none of the press pool — which included many non-MAGA journalists — called out that silly response, or even gently probed him about which robe-wearing specialty keeps magic beams and heavenly apparitions in its toolkit.

ENRAGING: Trump Has The Stones To Brag About His Tip Provision Helping With Medical Bills

Simmons has repeatedly talked about how even with insurance, her husband’s medical bills wiped out their savings, and Trump had the nerve to invoke that struggle after years of doing nothing but promising great health care and gutting Obamacare.

ENRAGING: Not One Question About DoorDash Grandma Being Cleaned Out By Medical Bills

This is without a doubt the most enraging part of this episode, because imagine if former President Joe Biden held this kind of ridiculous event. Now imagine that event played into on of his most notorious political weaknesses.

AWESOME: DoorDash Grandma Declines Invitation To Bash Trans People

It would have been more awesome if she had fully called him on the carpet like a true ally, but this will do:

PRESIDENT DONALD TRUMP: Well, it’s a very serious charge against them and the Democrats. They cheat. They can’t get elected with their policy. So their policy is no good. They want to have, I mean, open borders. They want have men playing in women’s sports. Do you think that men should play in women sports?

DOORDASH GRANDMA SHARON SIMMONS: I really don’t have an opinion on that.

PRESIDENT DONALD TRUMP:You don’t? I’ll bet you do.

DOORDASH GRANDMA SHARON SIMMONS: No, I’m here about no tax on tips.

AWESOME: DoorDash Grandma Didn’t Even Vote For Trump In 2024

During the photo op, Simmons deflected when Trump asked her about her vote:

PRESIDENT DONALD TRUMP: It’s such an honor to meet you. And I think you voted for me, do you think?

DOORDASH GRANDMA SHARON SIMMONS: Ah, maybe– (LAUGHS)

PRESIDENT DONALD TRUMP: I heard you’re a great supporter. We appreciate it.

But in remarks to reporters after the event, Simmons revealed that she had not had a chance to update her registration in time to vote for Trump. Maybe he ought to think about making it easier to vote, not harder.

CRINGEWORTHY: Some MAGA Reporter’s Hyper-Embarrassing Question

It’s cringe because it was asked, and because it’s actually a super-strong possibility.

REPORTER: The UFC fight that’s happening at the White House this summer, UFC typically numbers those fights consecutively, but should they label this one UFC 1776?

PRESIDENT DONALD TRUMP: That’s a good idea. I’ll tell that to Dana White. I like that idea.

Jesus (or healthcare worker) take the wheel!

I’ll give a couple of honorable mentions here. The lie that Simmons “saved $11,000.00” that Trump pushed and that Simmons corrected on Fox News was outrageous, and so were the reporters who failed to call it out.

And the Twitter sleuths who thought they cracked some big mystery when they produced her Congressional testimony as a “receipt” proving the whole thing was staged get a cringe “No Sh*t Sherlock” Prize.

Watch above via White House press pool.

This is an opinion piece. The views expressed in this article are those of just the author.

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