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By Sam Stevenson, Alia Shoaib, and Alice Gibbs
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President Donald Trump has reignited speculation about a possible 2028 presidential bid after posting a series of AI-generated "Trump 2028" images on Truth Social, including one carrying the message: "We are going to win."
The posts, shared on August 15, show Trump wearing hats emblazoned with "Trump 2028" and mark the latest in a long-running series of comments, jokes and social media messages that have referenced serving beyond his current term.
While the Constitution currently bars Trump from being elected president a third time, his latest posts have renewed debate over whether he is merely trolling political opponents or deliberately keeping discussion of a post-2028 future alive.
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One image showed Trump standing behind a "Trump 2028" podium while adjusting a matching red hat. Another depicted Trump wearing a dark "Trump 2028" cap alongside the words: "We are going to win."
The posts come just weeks after Trump joked at the White House Correspondents' Association dinner that he intended to run for a "fourth time" as president, before later showcasing a red "Trump 2028" hat.
This is not the first time Trump has embraced "Trump 2028" imagery. In late July, he shared a series of AI-generated images referencing another presidential campaign and appeared publicly wearing a red "Trump 2028" hat at the rescheduled White House Correspondents' Association dinner.
Newsweek reached out to the White House via email for comment.
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How Trump's 2028 Messaging Has Evolved
Trump's latest post stands out because it moves beyond merely displaying a "Trump 2028" slogan. The accompanying message, "We are going to win," adopts language typically associated with an active election campaign.
That evolution is likely to fuel renewed debate over whether Trump's repeated references to another run are simply political trolling, a branding exercise aimed at supporters, or something more deliberate.
While supporters often dismiss such remarks as political humor or trolling directed at critics and the media, constitutional scholars have repeatedly pointed to the 22nd Amendment, which states that "no person shall be elected to the office of the President more than twice."
The question is not new. What has changed is the number of times Trump has returned to the subject—and the varying degrees of seriousness with which he has addressed it.
From the Correspondents' Dinner to Trump's Latest Truth Social Posts
Speaking at the rescheduled White House Correspondents' Association dinner, Trump portrayed himself as doing the media a favor.
"You people have no idea how lucky you are. When I'm gone, you're all going to be broke," he said before delivering the punchline. "That's why tonight, to show just how much I care about the press, and I want to save your ratings. I'm pleased to announce my intention to, and this is somewhat of a scoop, my intention to run for a fourth time as president of the United States."
He then continued: "I think I won three times. Now I'm going to do it again."
Reports from the dinner described the comments as a joke directed at journalists in attendance, with Trump framing the announcement as a media "scoop" and later wearing a "Trump 2028" hat.
The August 15 posts suggest the theme has remained part of Trump's messaging weeks after the dinner remarks. In one image, Trump is shown adjusting a red "Trump 2028" hat while standing behind a podium bearing the same slogan. In another, a shadowy portrait of Trump wearing a black "Trump 2028" cap is accompanied by the words: "We are going to win."
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A Timeline of Trump's Third-Term and Post-2028 Comments
May 18, 2024
Months before returning to the White House, Trump invoked Franklin D. Roosevelt during a speech to the National Rifle Association in Dallas.
"You know, FDR 16 years—almost 16 years—he was four terms. I don't know, are we going to be considered three-term? Or two-term?"
The comments were delivered in a joking tone but introduced a theme that would repeatedly re-emerge.
November 13, 2024
After winning a second, non-consecutive term, Trump joked before House Republicans:
"I suspect I won't be running again unless you say he's so good we've got to figure something else out."
The room reportedly laughed, but the notion of finding an alternative route around term limits had entered the conversation.
January 25, 2025
At a Las Vegas rally days after taking office, Trump said it would be "the greatest honor" to serve "not once but twice—or three times or four times."
He quickly added that two terms would be the objective.
January 27, 2025
Addressing House Republicans at a GOP retreat in Miami, Trump quipped that he had raised money for "the next race."
"I think I'm not allowed to run again," he said.
February 6, 2025
At the National Prayer Breakfast, Trump again referenced another campaign beyond 2028, talking about future elections "despite the fact that they say I can't run again."
February 20, 2025
During a Black History Month celebration at the White House, Trump asked the audience:
"Should I run again? You tell me?"
After attendees chanted "four more years," Trump laughed and noted that the exchange would likely become a news story.
When The Comments Became More Serious
The most significant moment came on March 30, 2025.
In a telephone interview with NBC News, Trump was asked directly whether he was joking about pursuing another term.
"No, I'm not joking," he replied.
That interview marked a notable departure from the wink-and-nod style of many earlier remarks.
Later the same day aboard Air Force One, Trump struck a somewhat different tone, saying he did not want to discuss a third term because there was still a long time left in his presidency.
Even so, he again referenced widespread support among people urging him to remain in office.
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April 28, 2025
In an interview with The Atlantic, Trump again entertained the concept.
"That would be a big shattering, wouldn't it? Well, maybe I'm just trying to shatter."
The comment maintained ambiguity while keeping speculation alive.
Trump then added that there were "methods" by which it could potentially happen and suggested alternative arrangements had been discussed, though he declined to provide details.
August 18, 2025
During an Oval Office meeting with Ukrainian President Volodymyr Zelensky, Trump joked about wartime conditions delaying elections.
"Three and a half years from now ... if we happen to be in a war with somebody, no more elections. Oh, that's good."
The room laughed, but the comment prompted fresh scrutiny.
October 27, 2025
Asked aboard Air Force One whether he was ruling out another term, Trump answered:
"I would love to do it."
He then added: "You'll have to tell me."
February 5, 2026
During another NBC interview, Trump was asked whether he could envision remaining president beyond January 2029.
"I don't know. That would be interesting," he responded.
May 4, 2026
At a White House Small Business Summit, Trump again joked about a timeline extending beyond his current term.
"When I get out of office in, let's say, eight or nine years from now, I'll be able to use it."
The audience laughed, but the remark implied a presidency stretching into the 2030s.
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May 21, 2026
At the U.S. Coast Guard Academy commencement, Trump said that icebreaker ships under construction would begin arriving in 2028.
"I'm going to be here in '28. Maybe I'll be here in '32 too. I don't know."
The audience laughed, but the comment once again raised questions about whether Trump views the issue as a joke, a political provocation or something more.
July 24, 2026
Trump joked at the rescheduled White House Correspondents' Association dinner that he planned to run for president again and produced a red Trump 2028 hat.
July 26, 2026
Trump posted a flurry of AI-generated memes on Truth Social referencing running for a third term in office for 2028.
August 15, 2026
Trump shared two new AI-generated "Trump 2028" images on Truth Social. One depicted him behind a "Trump 2028" podium, while another included the message: "We are going to win." The posts reignited speculation over whether his repeated references to 2028 are intended as political humor or a more serious signal to supporters.
Can Trump Legally Seek Another Term?
Under the current Constitution, Trump cannot be elected president for a third term.
The 22nd Amendment states: "No person shall be elected to the office of the President more than twice." The amendment was ratified in 1951 after Franklin D. Roosevelt became the only president elected to four terms.
Because Trump has already been elected president twice, constitutional experts broadly agree that he is barred from winning another presidential election in 2028.
That has not stopped occasional political discussion about theoretical and highly contested alternatives, including constitutional amendments or other legal scenarios. Those ideas remain speculative and would face major legal and political obstacles.
Still, Trump's latest Truth Social posts demonstrate that the idea remains a recurring feature of his public messaging. Whether intended as a joke, a provocation, or a signal to supporters, the "Trump 2028" imagery has once again succeeded in thrusting the debate back into the political spotlight.
Update, 07/27/2026, 4:36 a.m. ET: This article was updated with additional information.
Update 08/17/2026, 08:30 a.m. ET: This article was updated with new information.
Contact Newsweek editor on this story: Edward Pearcey, Sam Stevenson and Emma Lee-Sang
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