Things didn't go well for President Donald Trump after a DoorDash delivery person wearing a "Doordash Grandma" T-shirt did not take the bait when he asked her if she is okay with transgender people competing in sports.
Trump staged a promotional moment in the Oval Office by receiving a McDonald’s delivery, using it to highlight his “no tax on tips” policy.
The delivery worker handed over two bags of food as Trump pointed to a reported tax refund as evidence of the policy’s benefits, calling the broader legislation a “great big beautiful tax cut bill.” The law, passed by Republicans, allows certain tipped workers—like bartenders and caddies—to deduct portions of their tip income from federal taxes between 2025 and 2028.
After the delivery, Trump fielded questions on a range of topics while the delivery worker, later identified as Sharon Simmons, stood beside him. At one point, he attacked Democrats for supporting transgender athletes, who have been targeted by the Trump administration.
Republicans have rallied behind the Trump administration’s executive order banning transgender women from competing in women’s sports, leading to a legal clash with Maine after its Democratic governor declined to cooperate, warning Trump that she'll "see him in court" after he threatened to withhold federal funding from the state. Maine has since prevailed in that case.
Trump turned to Simmons and asked:
“Do you think that men should play in women’s sports?”
Simmons shut him down:
“I really don’t have an opinion on that.”
When Trump insisted, “You don’t? I’ll bet you do," Simmons was firm:
“No, I’m here about no tax on tips."
You can watch what happened in the video below.
Trump's ruse didn't go so well—and people were quick to mock him in response.
White House Press Secretary Karoline Leavitt later posted that thanks to the "no tax on tips policy," Simmons "is using the $11,000 in tips that she made last year to support her family.
Although the White House has lauded the measure, critics say it may disproportionately benefit higher-earning tipped employees.
The Brookings Institution pointed out during Trump's 2024 campaign that "only 5% of workers in the bottom earnings quartile earn tips and could possibly benefit from the proposal." Notably, "even among tipped workers, 37% earn so little that they pay no federal income tax and so would not benefit from the tax cut."
