Trump Still Has a Bad Case of Obama Envy
The double spotlight on his failed Iran war and Obama’s Chicago celebration will make it worse.
WHETHER BY FATE, a devious Iranian conspiracy, or a major miscalculation by Donald Trump, the U.S. surrender in his failed 112-day “excursion” is coinciding with the triumphal opening of the Barack Obama Presidential Center in Chicago. The split-screen contrast is telling, from Iran to presidential libraries.
Trump’s “memorandum of understanding” to end his doomed war of choice on Iran does not fare well compared with the 2015 Obama deal that was constraining Iran’s nuclear program when Trump tossed it out in 2018. The “white flag memo” would be a more apt name for Trump’s document, or “memo of understanding that we’ll give you a better deal than Obama’s and leave the nuclear stuff for later.” But Trump did get to sign it at the, um, historically resonant Palace of Versailles instead of in Geneva on Friday—when it would have been competing directly with the grand opening of Obama’s presidential center.
Trump’s Obama envy has been an enduring psychopolitical feature of the national landscape for what seems like forever. He mentioned Obama’s name nearly two dozen times during the three-day G7 summit, by the New York Times’s count, and repeatedly insisted that his deal was better than Obama’s, despite glaring evidence to the contrary. Cartoonist Patrick Chappatte nailed the dynamic eight years ago. “What was so bad in that Iran deal?” asks an annoyed European Union representative. Trump’s reply: “Obama’s signature.”
Trump’s preoccupation with his predecessor has long centered on challenging Obama’s citizenship and his eligibility to even be president. He started raising questions about Obama’s birth certificate in early 2011, and his promotion of this “birther” conspiracy theory escalated after a famous incident that year at a White House Correspondents Dinner. It was Saturday night, April 30, at the Washington Hilton. Trump was in the room, and Obama was having some barbed fun about Trump’s “credentials and breadth of experience.” Let’s go to the transcript:
(Laughter.) For example—no, seriously, just recently, in an episode of Celebrity Apprentice—(laughter)—at the steakhouse, the men’s cooking team cooking did not impress the judges from Omaha Steaks. And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership. And so ultimately, you didn’t blame Lil’ Jon or Meatloaf. (Laughter.) You fired Gary Busey. (Laughter.) And these are the kind of decisions that would keep me up at night. (Laughter and applause.) Well handled, sir. (Laughter.) Well handled.
It turned out that a day before the dinner, April 29, Obama had authorized a U.S. Special Forces raid on a compound in Pakistan where U.S. intelligence believed Osama bin Laden was hiding. A day after the press dinner, on the afternoon of May 1, he ordered that the raid be executed. By that evening, barely twenty-four hours after cracking jokes about Trump and The Apprentice, Obama was addressing the nation about bin Laden’s death and the Seal Team 6 raid that killed him within its first nine minutes.
As Trump raked in money and fame as a reality-TV boss known for his “You’re fired” catchphrase, these were the decisions keeping Obama awake. The macho contest was no contest.
A tale of two presidential ‘libraries’
At the time, Trump was actively exploring a 2012 presidential run, which provided more fodder for Obama. “Say what you will about Mr. Trump, he certainly would bring some change to the White House. Let’s see what we’ve got up there,” Obama said at the WHCA dinner, as screens showed “Trump White House Resort and Casino.”
Two weeks after that fateful night, Trump decided against running. But the idea didn’t die. What better way to prove his manhood to Obama, or anyone else, for that matter, than by becoming commander-in-chief of the world’s largest military? He did it for real in 2016 and won. He did it again in 2024 after losing in 2020, and won a second term. And Obama’s joke about the resort and casino is not funny anymore.
The Oval Office is crammed with golden trim, gilded frames, and tacky gold tchotchkes. (The new Obama center has an Oval Office replica that will make you pine for those days, whether you liked him or not.) The Rose Garden is a concrete patio with Mar-a-Lago lookalike tables and umbrellas. The historic White House and grounds are a showcase for Trump-MAGA values—bloody fights for fun and profit and a massive $600 million ballroom, half financed by taxpayers, under siege in court. The whole capital is a stage for self-promotion, self-enrichment, and self-aggrandizement. Crypto scams. Foreign deals. A 250-foot high “Triumphal Arch,” a public golf course takeover, and a “National Garden of American Heroes”—unless lawsuits stop them.
Florida, Trump’s official home state these days, is getting a piece of the action via the Trump presidential library. Or will if the plan survives a lawsuit filed after Trump made clear—i.e., said out loud—that “I don’t believe in building libraries or museums.” He intends to build a 47-story hotel (get it? 47th president?) on the “immensely valuable” downtown Miami parcel, now a parking lot, gifted by Miami-Dade College. Trump floated the idea of an Air Force One plane in the lobby. But mainly, he intends to cash in—illuminating for the umpteenth time the toothlessness of the Constitution’s Emoluments Clauses banning states and foreign nations from giving presidents financial benefits.
By contrast, the Obamas wanted to invest in a diverse, urban area, and “to create a hub of recreational, cultural, and economic activity.” They chose Jackson Park, site of the 1893 World’s Fair, in South Side Chicago, where they started out. Celebrity performers and speakers participated in a livestreamed dedication Thursday, with a public “Grand Opening Weekend” starting Friday—which happens to be Juneteenth.
The complex, designed to stoke the local economy, already has energized locals with strong opinions, pro and con, on its stark main building: a 225-foot granite-clad tower, gray and geometric, punctuated by a large stained glass window. But there’s little else to argue about. The location, rich in black history from Pullman porters to the Great Migration, now expands to include the Obamas’ pathbreaking journey as the first black president and first family. Beyond that, this is no Trump hotel for affluent Americans. The Obamas have purposefully reached out to their community and country.
‘Dumbest war yet’
“Enjoy a free, open-house style event celebrating community, creativity, and joy,” the site says of opening weekend. “Dance to music on the plaza, create art with your family, and snapshot your place in this historic moment.” This presidential center has a basketball court and a public library branch. It has a John Lewis Plaza and an Elie Wiesel Auditorium. It has digitized National Archives records of the Obama administration for anyone to view and research. It has a playground for children and programs for teens. It has a fruit and vegetable garden, recalling Michelle Obama’s White House Kitchen Garden—part of her “Let’s Move” push for kids to eat healthier food and get more exercise. You may remember that drew conservative backlash. But now MAGA, Trump, and Robert F. Kennedy Jr. count “MAHA moms” as part of their coalition.
Trump is paying attention, of course. He has criticized the Obama center as over budget (!), and this month he posted an AI-generated photo of the tower with a trash bag on top. He may soon notice that the Obama museum highlights the Joint Comprehensive Plan of Action, Obama’s painstakingly negotiated, multinational Iran nuclear agreement. It’s showcased to illustrate his emphasis on diplomacy and engagement with adversaries.
This could have been Trump’s mode, but after campaigning in 2016 as a non-interventionist, he discovered that he liked using force. Military aggression was his go-to tool in his first term, and he’s picked up the pace, scale, and intensity in his second term—from illegally killing people on Caribbean fishing boats without evidence or due process, to imposing regime change on Venezuela, to his designs on Greenland and Cuba, to his Iran misadventure that has killed thirteen Americans and thousands of Iranians, handed Iran what looks like permanent control over the Strait of Hormuz and the world oil trade, decimated the U.S. weapons supply, and cost U.S. taxpayers tens of billions of dollars.
“For what? What was the point of that war? A more radical Iranian regime that now controls the Strait of Hormuz? Dumbest war yet,” former Obama speechwriter Jon Favreau wrote on social media. Added Ben Rhodes, who was Obama’s deputy national security advisor: “This deal reopens a body of water that was open before the war and begins a nuclear negotiation far narrower than what Trump was seeking before the war. All at a staggering cost to the entire world while leaving an IRGC-led government that feels strengthened.”
And so the humiliations continue, even though Obama is out of office. Scholars have “credited” Trump with fueling the birther idiocy long beyond what should have been its natural lifespan. “Though the movement was continuously debunked by a myriad of people, birthers remarkably managed to keep the conspiracy alive and relevant, due in large part to Donald Trump. Analysis of birther rhetoric, and specifically Donald Trump’s use of it to continually undermine Barack Obama, provides a particularly robust understanding of the rhetorical forms that facilitate the resiliency of conspiracy,” Bates College researchers wrote in 2019 in the Journal of Hate Studies.
Obama released a long-form copy of his birth certificate in 2016, and Trump as president in 2017 speculated that it had been faked. He has moved on to much grander conspiracies and lies since then, topped by his imaginary win in 2020. But he has never stopped trying to top Obama.
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This pretty much sums it up. Well done.
An excellent essay that touches the most salient points.
I used to think that Obama living rent-free in Trump's head was motivated by racism (it still is), but more recently, it seems to be age and health.
Obama, at 64, is in infinitely better health than Trump; there's no comparison.
Obama is a stark reminder of Trump's mortality and Trump hates that.