Karoline Leavitt, the White House press secretary, thought she had the perfect feel-good moment to share when she posted a video of Donald Trump at the U.S. Open men’s final on Sunday. Instead, it quickly became an internet punching bag.
Leavitt uploaded a clip to X, showing Trump signing red hats and tossing them into a cheering crowd. Alongside the video, she gushed, “The People’s President and the coolest boss ever. Signing hats for fans at the #USOpen.”
The post was meant to show Trump’s popularity in the middle of a high-profile sports event. His supporters flooded the comments with praise, calling it proof that the president remains a star attraction. But critics quickly pointed out a glaring contradiction: much of the stadium was booing.
Spectators at Arthur Ashe Stadium made their feelings known as Trump appeared on the big screen. He was met with audible jeers, not just once but several times throughout the evening. One of the loudest moments came during the national anthem when his image popped up on the Jumbotron. The mix of cheers and boos leaned heavily toward disapproval, according to those in attendance.
That didn’t stop MAGA fans online from framing Leavitt’s post as evidence of Trump’s broad support. “Undeniable proof of his popularity,” one loyalist wrote, echoing a theme repeated across pro-Trump accounts. The hat-tossing, complete with fans scrambling to catch souvenirs, gave the appearance of a rockstar moment.
Still, outside the Trump bubble, the footage looked a little different. Many saw it as staged political theater, pointing out that boos drowned out the applause. Critics accused Leavitt of ignoring the larger picture in favor of flattering her boss. “If he’s the people’s president, why is the crowd booing so loudly?” one reply shot back.
It’s not the first time Trump has gotten a frosty reception at major sporting events. He was famously booed at the World Series in 2019 and again at the UFC in Madison Square Garden. This weekend’s tennis match seemed to fit the same pattern: strong enthusiasm from loyal supporters mixed with loud resistance from a broader audience.
Leavitt, who is only 27 and already one of Trump’s most visible defenders, has leaned into her role as a social media warrior. Her posts often highlight Trump as a man of the people, even when the reality looks more complicated. By calling him “the coolest boss ever,” she tapped into that same playbook, but the response suggests not everyone was buying it.
Trump’s appearance at the U.S. Open wasn’t on the official program, and it sparked speculation that he’s still testing ways to connect with mainstream audiences ahead of the 2024 election. Whether the boos matter to his core supporters is another question. For them, the takeaway is still the image of Trump smiling, signing hats, and tossing them into a sea of red caps.
For others, though, the lasting impression might be the sound of thousands booing in unison at one of the world’s most prestigious sporting events.