The Long History Of Donald Trump Being Jealous Of Barack Obama

During his first term, President Donald Trump appeared overshadowed by his predecessor, Barack Obama. The former president took up so much space in the divisive politician's mind that he was all he could talk about. In 2019, the president's mention of Obama's name increased in frequency, so much so that some reporters felt the need to point it out. In June of that year, Trump brought Obama's name into a conversation 106 times. July saw 68 mentions, August, 61, and October recorded 80. Washington Post columnist Eugene Robinson summarized Trump's inability to cast Obama out of his mind succinctly, diagnosing the president with a "chronic and debilitating case of Obama envy."

Trump's Obama envy hasn't stopped. As much as he seems to loathe his predecessor, he also appears to long for his approval — and friendship. Trump's reported request for Obama at Jimmy Carter's funeral in 2025 confirmed what we all knew — he's dying to play a game of golf with the former president. Probably so he could, at least, outshine him on the green, since it's become clear that attempts to do so as the head of the country's highest office are futile.

Trump might blame Obama for the country's problems, have issues with his middle name, and abhor that the beloved president has a degree from Harvard. However, his obvious jealousy hints that he wishes he could be more like him, or at least call him an ally. If you thought orange was a bad look on Trump, you're about to find out that green is a far more unflattering color.

If there's one person who knows the inner workings of Trump's mind, it's his former fixer and personal lawyer, Michael Cohen. As pundits tried to understand Trump's fixation with Obama, Cohen offered helpful information during a September 2020 interview with Rachel Maddow. "He's Black. He went to Harvard Law. He graduated at the top of his class. He's incredibly articulate," Cohen explained, per X. "He is all the things that Donald Trump wants to be, and he just can't handle it. So, what do you do if you can't handle it, and you're Donald Trump? You attack it." While some might attribute Cohen's assertions to sour grapes, given that Trump has done his best to trash his reputation after the lawyer turned on him, what he said made quite a bit of sense, and others have made similar assessments.

Journalist and Trump biographer, Michael Wolff, told The Daily Beast Podcast in May 2025 that Trump's vendetta against Harvard University, which he launched shortly after retaking office, wasn't random — it was retribution. "He didn't get into Harvard," Wolff asserted, alleging that the president has resented Ivy League schools ever since. There isn't any concrete proof to back up Wolff's claims. Trump did, however, address the rumor on Truth Social, per Newsweek, fuming: "Michael Wolff, a Third Rate Reporter, who is laughed at even by the scoundrels of the Fake News, recently stated that the only reason I'm 'beating up' on Harvard, is because I applied there, and didn't get in. That story is totally FALSE, I never applied to Harvard." The president's vehement denial almost makes us think Wolff and Cohen might have been telling the truth after all.

When Trump gets upset about something you said, you'd best believe it's because you hit a nerve. Trump's fragile ego doesn't do well with criticism — or public mention of his jealousy of Obama, for that matter. It should, therefore, shock absolutely no one that the president went on a social media rant after "The View" host Joy Behar called him out on his Obama envy during a July 2025 episode. It came after Trump was desperately trying to distract his base from the Epstein files by accusing Obama of treason.

"Obama is everything that he is not — trim, smart, handsome, happily married, and can sing Al Green's song 'Let's Stay Together' better than Al Green. And Trump cannot stand it. It's driving him crazy," Behar asserted. Behar's co-hosts agreed. Trump decidedly did not, but whether he actually knew that Behar said this remains a mystery, because he never actually commented on the segment. Given that Trump hasn't been able to rein in his temper when it comes to assertions that he's jealous of his predecessor, this was rather odd.

Instead, a White House spokesperson condemned Behar's allegations, telling The Hollywood Reporter in a statement, "Joy Behar is an irrelevant loser suffering from a severe case of Trump Derangement Syndrome. It's no surprise that 'The View's' ratings hit an all-time low last year. She should self-reflect on her own jealousy of President Trump's historic popularity before her show is the next to be pulled off air." We can't help but notice that the statement reads very much like a Truth Social post from the commander-in-chief himself.

There are some glaringly obvious signs that Trump's health is in decline, but the president is in complete denial, despite the fact that his incessant health ramblings are pouring gasoline on those cognitive decline rumors. It's worth noting that, even when it comes to his health, Trump compares himself to Obama. When Trump delivered a speech at the White House Hanukkah reception in December 2025, his former White House doctor, Ronny Jackson, was also in attendance. Trump saw an opportunity to tout his health, so he pointed to Jackson in the crowd.

"He was my White House doctor. Ronny was asked, 'Who's the healthiest of all? Was it Barack Hussein Obama? Was it Sleepy Joe Biden? Or was it Donald Trump?' And he said 'Trump was by far the healthiest,'" Trump enthused, per People. Jackson, however, isn't exactly the most upstanding physician out there. He previously served in the Navy but was demoted in 2022 after he was accused of misconduct during his time at the White House. This included being disrespectful toward colleagues, drinking, and taking sleep medication while on duty. No wonder he deemed Trump fit as a fiddle.

Furthermore, during a 2026 interview with The Wall Street Journal, Trump said he takes far more aspirin than prescribed, and has been doing so for over 25 years. "They say aspirin is good for thinning out the blood, and I don't want thick blood pouring through my heart. I want nice, thin blood pouring through my heart. Does that make sense?" he told the outlet. He's probably trying to make his blood thinner than Obama's.

One would think that Trump would have put his obsession with Obama behind him by the time he retook office in 2025, but alas, that is not the case. As much as the president brought up his predecessor's name during his first term, he's continued to drop his name into random conversations during his second, and has even employed the former president as a distraction from the Epstein files. Trump made headlines when he posted an AI-generated video to social media in July 2024 showing Obama getting arrested inside the Oval Office and thrown into a jail cell. The video temporarily disrupted a news cycle that was laser-focused on the Trump administration's failure to deliver on its promise to release the Epstein files.

There has also been Trump's obsession with abolishing the Affordable Care Act, also known as ObamaCare. The divisive politician can't seem to stand the fact that the program has Obama's name and has tried everything in his power to do away with it and replace it with something bearing his own moniker. He has been unsuccessful thus far.

The most telling sign that Obama continues to live rent-free in Trump's mind, however, was perhaps the divisive politician's conduct leading up to the 2020 election. As he tried to hype his base on the campaign trail, Trump repeatedly accidentally referred to his rival, Joe Biden, as Obama and, at one point, claimed he'd beaten him in the 2016 election. Last time we checked, it's very hard to confuse Hillary Clinton with the former president.

Perhaps the reason Trump has never officially won a Nobel Peace Prize is that the Nobel Committee simply can't bring itself to further inflate his already overblown ego. There's also the fact that Trump has sown more discord in the country during his two terms than his predecessor, Obama, who received the coveted prize in 2009, barely eight months into the first term of his presidency. We have a suspicion this keeps Trump, who has repeatedly tried and failed to pocket the prize, up at night.

In 2025, Trump repeatedly proclaimed himself a worthy recipient, while claiming that Obama should never have been awarded the prize. "He got a prize for doing nothing," Trump said during an October 2025 briefing in the Oval Office, per X. "He got elected and they gave it to Obama for doing absolutely nothing but destroying our country. He was not a good president," Trump jabbered. It's worth noting that one of the reasons offered by the Nobel Committee for Obama's win was that he had displayed "extraordinary efforts to strengthen international diplomacy and cooperation between peoples," per the Nobel Prize website. The same can't exactly be said for Trump.

Trump is not above making up stories to put Obama in a bad light. Those who don't accept what he says at face value, however, are well aware that half of the gibberish Trump has uttered about the former president is just that. Trump's obsession with Obama started long before he ran for president. In 2011, he elevated claims that Obama wasn't a legitimate president because he wasn't born in the United States. These claims were entirely false, but Trump repeated them nonetheless. He demanded that Obama make his birth certificate public to prove his U.S. citizenship. Obama eventually adhered, but that didn't stop Trump — he simply moved to question the document's authenticity. In September 2016, Trump finally admitted that Obama was, indeed, born in the United States.

Not long after his second term commenced, Trump blasted another made-up story about Obama, this time through his Director of National Intelligence, Tulsi Gabbard. Gabbard came forward out of the blue, accusing Obama of treason during a July 2025 press briefing. She claimed he tried to stage a coup during the 2016 election and that the Russian interference ahead of the election was a conspiracy led by the former president to undermine Trump. Gabbard made these claims even though subsequent investigation found proof of Russian interference and that Republicans, including Trump's now Secretary of State, Marco Rubio, signed off on it. These were serious allegations, however, and even though Obama has mostly ignored the vitriol coming from the Trump White House, he released a statement in response to Gabbard's briefing. "These bizarre allegations are ridiculous and a weak attempt at distraction," the statement read, per The Guardian.

In 2024, Trump's ego blasted into overdrive as he made the wildest claim about Obama yet — he boasted that he believed the former president would be casting his vote for him in the election, not for former Vice President Kamala Harris, despite Obama having endorsed the latter. One cannot imagine the former president supporting Trump in any way, let alone in his bid to run the country once more. Of course, Trump's attempts to surpass Obama's achievements continue, and in January 2026, he appeared to recreate the iconic Situation Room photograph taken of Obama and his aides as they kept close watch on a military operation to neutralize Osama bin Laden in May 2011.

The White House's X account posted a black-and-white snap of Trump and his close aides, including Secretary of State Marco Rubio and White House Deputy Chief of Staff Stephen Miller, as they oversaw the capture of Venezuelan President Nicolás Maduro. Pundits in the comments quickly pointed out the similarities between the black-and-white snap and the iconic photograph of Obama and his aides in 2011, with one penning on X, "lol, you want to be Obama so bad. With you drapes and your bootleg scif while using X [sic]."

In December 2025, Trump's presidential walk of fame got a tacky upgrade (and it was downright embarrassing). The president opted to add plaques to the photographs of his predecessors, which adorn the hallway leading to the Oval Office. The plaques were written in a similar style to his Truth Social posts, littered with randomly capitalized words and on-the-nose insults. While former President Biden was probably the worst off, Obama wasn't spared.

Trump called Obama "one of the most divisive political figures in American history" (was Trump perhaps projecting a little with this assertion?), and yammered on about the Affordable Care Act being a massive failure, calling it "the highly ineffective 'Unaffordable' Care Act." He also didn't pass up the opportunity to bring up the Russian interference in the 2016 election, repeating claims he made earlier that year that it had all been a hoax orchestrated by his predecessor. "Obama also spied on the 2016 Presidential Campaign of Donald J. Trump, and presided over the creation of the Russia, Russia, Russia Hoax, the worst political scandal in American history," the plaque reads, per The Sun.

CNN's chief White House correspondent, Kaitlan Collins, pointed out on Instagram the plaques' similarity to Trump's divisive Truth Social posts and noted that White House Press Secretary Karoline Leavitt, who is as Trump-obsessed as they come, proudly said that the president "handwrote" the plaques. Given the language used — and the fact that some of the information on the plaques is entirely false — there's no doubt about that.

As Trump stepped on the campaign trail in 2020, he couldn't help but make Obama the main topic of conversation. The former president delivered scathing criticism of Trump as he canvassed for his own party ahead of the election. He asserted that the divisive politician didn't take the presidency seriously and had failed to show good leadership during the pandemic. Trump clapped back the first chance he got — not with facts, but with insults.

"You know how many people he's drawing at these rallies? He's drawing flies ... 20, 30, 40. Not quite this crowd," Trump said at a rally, per The Nation. He continued, "[Obama] gets up and then they say, 'Oh, he's so rhetorically good.' I never thought he was a good speaker personally. I really never did. Then they say he's so handsome. He's so handsome. Oh, okay, he's so handsome. He's so handsome. Oh, okay. All right." Clearly, Trump was (and still is) dealing with some serious self-esteem issues.

It didn't help that Obama chastised Trump in 2016 for being a crybaby as he made false claims that the election was rigged before it had even started. "[Trump should] stop whining and go try to make his case to get votes," Obama said during a Rose Garden news conference, per The New York Times. Trump repeated this mistake ahead of the 2020 elections, spending way too much time laying into Obama instead of Joe Biden, who was his actual opponent. During this time, he made up a story that Obama was guilty of the "greatest political crime in the history of our country," per NBC News. When asked to elaborate on said crime, he was unable to do so.