President Donald Trump spent Monday night firing off 55 posts on Truth Social in the span of three hours, and if anybody thought he was finally taking a break from talking about Barack Obama, absolutely not. Obama was front and center through the whole posting spree, with Trump sharing conspiracy theories, arrest fantasies, and accusations of treason that sounded like somebody handed a cable news comment section an energy drink at midnight.
The late-night flood began around 10:14 p.m. on May 11 and continued until after 1 a.m. on May 12. A recent Washington Post/ABC News/Ipsos poll found that 59% of Americans believe Trump lacks the mental capacity to lead the country, and honestly, a three-hour overnight posting marathon about Obama probably is not helping calm anybody down.
Now, this obsession has been hanging around for 15 years, including birtherism, wiretapping claims, and AI-generated arrest videos. At this point, Trump and Obama have one of the longest-running rivalries in modern politics, except this one somehow keeps getting stranger every season.
55 Posts, Three Hours, And One Very Familiar Target
Most of the posts were reposts from supporters and MAGA personalities, plus several AI-generated memes tossed into the mix for dramatic effect. One repost called for “Arrest Obama the traitor.” Another said, “Arrest them all. Prosecute them all. Incarcerate them all at once for treachery, treason, and seditious conspiracy to overthrow the United States Government. But first, Barack Obama.”
Another post labeled Obama “the most DEMONIC FORCE in American politics in decades,” while several others falsely accused Obama and his allies of rigging both the 2016 and 2020 elections. Trump also widened the target list to Hillary Clinton and former FBI Director James Comey, because apparently, the reunion tour was expanding.
Then Tuesday morning arrived, and Trump was somehow still going. He posted an AI-generated image showing Obama, Joe Biden, and former House Speaker Nancy Pelosi bathing in a filthy Lincoln Memorial Reflecting Pool with the caption “Dumacrats Love Sewage.”
The Night Obama Roasted Trump And Possibly Changed American History Forever
To really understand why Trump keeps circling back to Obama, you have to rewind to 2011, back when Trump became the loudest face of the birther movement. He publicly questioned whether Obama was born in the United States, claiming he had investigators in Hawaii digging into Obama’s birth records, which already sounded wild even before social media became what it is today.
Obama released his long-form birth certificate in April 2011. Then, just days later, he stepped onto the stage at the White House Correspondents’ Dinner and roasted Trump directly while Trump sat in the audience looking deeply unamused. Obama mocked Trump’s presidential ambitions and his role on Celebrity Apprentice, and the whole thing became political pop canon immediately.
Obama’s former chief speechwriter Jon Favreau later explained the strategy behind the jokes, saying: “What we wanted to accomplish more than anything was show people how absurd he was.” Comedian Seth Meyers, who also roasted Trump that night, later approached him at a charity event to thank him for being a good sport.
Trump’s response was short and very on brand. He told Meyers: “You went too far.” Trump did not formally acknowledge Obama was born in the United States until September 2016, and even then, the statement included no apology.
From “Obamagate” To AI Arrest Videos, the Obama Fixation Just Kept Escalating
The accusations did not slow down after Trump entered office. In March 2017, he tweeted that Obama had wiretapped Trump Tower, a claim the Justice Department refuted while investigators found no evidence to support it.
Then came “Obamagate.” In May 2020, Trump declared it “the greatest political scandal in the history of the United States.” When reporters pressed him to explain the alleged crime, Trump responded: “You know what the crime is. The crime is very obvious to everybody. All you have to do is read the newspapers, except yours.”
Things escalated even further in July 2025 when Trump posted an AI-generated video showing FBI agents dragging Obama out of the Oval Office and throwing him into a jail cell while “YMCA” by the Village People played in the background. Because apparently somebody looked at a political feud and decided it needed editing software and a soundtrack.
maybe the funniest video I’ve ever seen pic.twitter.com/x2oPAUyCpe
— Erik Strobl 🦝 (@erikstrobl) May 11, 2020
Days later, Trump doubled down while speaking to reporters. “Barack Hussein Obama is the ringleader. Hillary Clinton was right there with him, and so was Sleepy Joe Biden. And so were the rest of them, Comey, Clapper, the whole group.” No criminal charges have ever been filed against Obama or Clinton in connection with any of these allegations.
Congressman Jim Himes later addressed the claims on Face the Nation and said there was “not a single judge” who would treat the allegations with anything other than “laughter that will be heard from the Atlantic to the Pacific.”
The Few Times Obama Has Responded, He Really Has Not Held Back
Obama’s representatives did not respond to the latest posting spree, although they previously declined comment to The Washington Post. His office did issue a rare statement in July 2025 saying it does “not normally dignify the constant nonsense and misinformation flowing out of this White House with a response,” but added the allegations were “outrageous enough to merit one.”
Obama also addressed the broader issue during an appearance on The Late Show with Stephen Colbert on May 6. “We can survive a lot, bad policy, funky elections… there’s a bunch of stuff that we can overcome. We can’t overcome the politicization of the justice system, the awesome power of the state.”
He continued: “You can’t have a situation in which whoever is in charge of the government starts using that to go after their political enemies or reward their friends.” In a separate interview with The New Yorker, after Trump posted a racist video depicting the Obamas as apes, Obama said: “I don’t take it personally. I mean, I’m always offended when my wife and kids get dragged into things, because they didn’t choose this.”
While Trump was busy posting on Truth Social through the night, Obama was in Austin campaigning for Democratic Senate candidate James Talarico and gubernatorial candidate Gina Hinojosa. Trump, meanwhile, headed to Beijing the next day for a summit with President Xi Jinping.
Why This Chapter Suddenly Feels Way More Serious Than The Others
Former FBI Director James Comey, who is currently facing federal prosecution over a photo of seashells that the DOJ alleges was a threat to Trump’s life, reacted to the posting spree during an appearance on CNN. “He doesn’t seem okay to me, and I know that sounds like a political shot. It seems like there’s something wrong with the man.” He later called the posts “middle of the night, obsessive” and added: “You seem nuts, buddy.”
White House spokesperson Davis Ingle referred reporters back to Trump’s Truth Social posts and declined further comment. The Justice Department also declined to comment.
What makes this latest chapter stand out is the actual power behind the rhetoric now. Todd Blanche, the acting Attorney General, who is repeatedly referenced in these posts, replaced Pam Bondi in April and previously served as Trump’s personal criminal defense attorney during the prosecutions against him in 2023 and 2024.
For the first time in this very long Trump versus Obama saga, the person Trump is publicly pressuring to prosecute a former president actually has the authority to try.