Don Jr. Tried To Shade A Senator & Accidentally Put Trump's Biggest Insecurity On Blast

As much as the Trump family wants to be known for ego and brute force, they are also seemingly a crew full of profound insecurities. Donald Trump Jr., who often wants to impress his father Donald Trump, has instead mostly found himself exposing insecurities they share. Take, for example, the time Don Jr. made a mess by talking about his father's hair too much, revealing a shared fear. It seems that Don Jr. has once again potentially stepped in some hot water with Donald by trying to take down New York Senator Chuck Schumer. In his Instagram Stories, Don Jr. reposted a video of Schumer discussing the president's poor poll numbers, with Schumer himself deflecting at his own miserable polling.

While the video is a classic example of politics coming back to bite a politician — and members of Schumer's own party have asked him to step down from his leadership role — it still highlights one key thing that Don Jr. forgot. His father, the president who desperately wants to be liked, does have some incredibly low poll numbers. According to The Washington Post, Donald Trump's favorability rating dipped below 40% in April 2025. In fact, these poll numbers are something Donald railed against at his rally in Warren, Michigan. "The fake polls," was how Donald referred to them while onstage (per Politico). With the president's dwindling rally sizes also being a sore subject, perhaps Don Jr. was trying to lighten the mood by making fun of Schumer. Although he could have just accidentally opened the door for more criticism.

With the first 100 days of his second term behind him, President Donald Trump is fully confronting many of his insecurities. After Trump didn't fully fill up the arena in Michigan on April 29, 2025 Senator Bernie Sanders hit Trump where it hurt by pointing out that Sanders himself had pulled in a much larger crowd for his "Fight Oligarchy" tour. As if this and his miserable poll numbers weren't enough, there's also the curious case of Trump's many portraits.

After taking an off-putting but stern official White House portrait, Trump decided one was not enough. In a move that indicates his fragile ego needs him to see himself everywhere, Trump installed an even tackier portrait of himself. Not only that, but he shoved it between two formal portraits of former First Ladies Laura Bush and Hillary Clinton. That seems like proof that he feels the need to suck all the attention in the room, especially around women. This, of course, happened after Trump had a meltdown on social media about what he deemed to be an unflattering portrait.

While these tantrums are mostly par for the course with Trump, it does seem that his second term is shaping up to have him confront much of what scares him. Crowds are down, his popularity is tanking, and even his oldest son can't be trusted to make a post to social media without accidentally exposing an insecurity.