You knew it was coming. To offer the Book of Thanos, it was … expected.
The second Trump began tweaking the establishment’s head by talking about a fourth word, it was just a matter of day. Eventually, the Democrats were gonna look around and say,” Hey! We’ve got a two-term leader of our own”!
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Really, they have two: Bill Clinton and Barack Obama. But the Clinton times are the Democrats ‘ type of Gen X: All sort of remembers they actually existed. ( Although, in light of Russia’s war in Ukraine, it’s likely that future historians will excoriate the Clinton administration for blundering through the post-Cold War period. In many ways, the Clintonites set the stage for the mess we’re in. )
No, it wasn’t gonna be Shiny Willy. It was always gonna get the other person — the unquestioned, all-time hero of overpromising and underdelivering: Barack Hussein Obama.
Look, TrumpKO’ing Kamala Harris was good, but let’s be fair: It was kind of unsatisfying. That’s not the game we’ve been dying to view.
But Donald Trump versus Barack Obama in a war of second words? Getcha snack available!
The hashtag# Obama2028 is now trending on X. Here’s a little sequencing:
# Obama2028 https ://t.co/oBlPtxA6rT— Brian Kelly ( @Brpkelly ) March 31, 2025
# Obama2028 https ://t.co/40hcmGPltt— Dr. G ( @GinnyMcDonald8 ) March 31, 2025
# Obama2028 pic. twitter.com/w4A2JUjrSj— Voice of Reason ( @raggapegs ) March 31, 2025
# Obama2028 #thirdterm pic. twitter.com/oNaJjHcNyH— SquirrelsJustWannaHaveFun ( @Normaninvador76 ) March 31, 2025
President Trump said he’d like to work against Obama:
President Trump said Monday he’d been willing to work against former President Barack Obama— if the US Constitution is changed to allow the men to seek a second term.
” I’d appreciate that — that had, that would be a great one”, Trump, 78, told reporters in the Oval Office as he was joined by Kid Rock, who wore a bedazzled dark clothing and a corresponding cowboy hat, at an executive order signing intended to suppress concert ticket killing.
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Trump and Obama have a long and tangled history. During Obama’s first term, then-TV star Donald Trump fanned the flames of the birther movement, which questioned Obama’s place of birth:
An’ extremely credible source’ has called my office and told me that @BarackObama’s birth certificate is a fraud.— Donald J. Trump ( @realDonaldTrump ) August 6, 2012
President Obama was far from innocent in their feud. Who could forget his blistering, mean-spirited attack on Donald Trump at the White House Correspondents ‘ Dinner:
” I know that he’s taken some flak lately, but nobody is happier, no one is prouder to put this birth certificate issue to rest than The Donald”, Obama remarked. ” And that’s because he can finally get back to focusing on the issues that matter, like did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac”?
” All kidding aside, we all know about]Trump’s ] credentials and depth of experience. For example, in an episode of ‘ Celebrity Apprentice,’ at the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks … You, Mr. Trump, recognized that the real problem was a lack of leadership… so you fired Gary Busey. These are the kinds of decisions that keep me up at night. Well handled, Mr. Trump”.
For all the complaints of Trump’s “mean tweets” and snark, the Democratic Party had perfected the art of personal attacks long before the invention of social media. In the aforementioned example, the Leader of the Free World decided to ridicule and demean a private American citizen.
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It didn’t age very well, did it?
Related:  , Guess Who’s Coming to Dinner: Bill Maher, Donald Trump, Kid Rock — and the World’s Wackiest Dinner Party
Both men would be well-armed in a hypothetical matchup between Obama and Trump. Fundraising certainly wouldn’t be a problem, on Obama’s side especially, his cup would spilleth over. Donors love the Obamas! Hell, they gave over$ 800 million to his presidential library! From genuine liberal beliefs to pandering and/or “virtue signaling”, their motivation for donating to Obama might be multifaceted, but the end result is the same: Obama would be the most well-funded candidate in world history.
Of course, Trump has some wealthy friends, too.
Obama’s calling card of” Hope and Change” and” Yes We Can”! worked wonderfully in 2008 and 2012. Those two phrases embodied the newness — and aspirational desires — of the electorate.
But would” Hope and Change” make sense for a president running for a THIRD term?
The possibility — and untapped potential — of Obama always exceeded the actual product. As a president, Obama was more smoke than fire. In one of the weirdest DEI outreaches, he was even awarded the Nobel Prize on day one. But in retrospect, his administration accomplished precious little. ( And as a cautionary tale, had Trump not trashed Obama’s insane 2015 Iran deal, the Mullahs in Iran would’ve had legal authority to advance their nuclear development this year, in 2025.)
Obama’s greatest accomplishment was his personal biography: His legacy as the first black president. And I’m not trying to be derisive, because that was awfully important. Communicated one way, it could’ve inspired generations of young people: America is a special place! Anyone can reach the top! It doesn’t matter if you’re black, white, rich, or poor: If you work hard, pray hard, and dream big, all things are possible! If Barack Obama did it, so can you!
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Alas, the exact opposite happened: Obama leveraged his credibility as the first minority president to give credence to those who viewed EVERYTHING through a racial prism. All previous liberal restraints were removed, the Democratic Party became the party of the 1619 Project. The sum total of American history was now reduced to racial exploitation.
Ronald Reagan talked about a” shining city on a hill”. George H. W. Bush spoke of a” thousand points of light”. Trump promised to” Make America Great Again”.
Obama’s message was very different: America is a land of white supremacy,” stupid cops”, and institutional racism.
And Obama himself is very different. In 2008, he was the young, fiery upstart who upset the applecart, outdueled the Clintons, and exuded vibrance and charisma from every pore.  ,
Now?
He’s old and gray. Seems kind of lazy, too.
Best you can say about the Obama years is, after everything was said and done, much more was said than done.
A battle of third-term presidents almost certainly wouldn’t happen, but despite Obama’s superior record in the Electoral College, a 2028 race between Trump and Obama would end in Obama’s defeat. On the surface, Obama has the upper hand, but just below the trajectory of sight, he faces too many headwinds.  ,
Come 2028, the” Hope and Change” message will be 20 years dated.
And honestly? I think Trump would outwork Obama. Say what you want about our current president, but he’s the freaking Energizer Bunny: He. Does. Not. Stop! His energy level is superhuman.
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Obama isn’t built like that. He doesn’t want to work any harder than he has to. And if he was ( borderline ) lazy as a young man, he’d probably be lazier as a 67-year-old, which would be his age in 2028.
Obama versus Trump would be like Muhammad Ali versus Joe Louis— or maybe Alexander the Great versus Genghis Khan. Be a helluva dream match!
No, it won’t happen, but it’s fun to speculate.
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