If former President Barack Obama looked tired and frustrated during his appearance at Hamilton College last week, it’s because he probably was—and not just with the question-and-answer format.
After reading through his remarks, one thing becomes clear: Obama is wrestling with a legacy that’s slipping through his fingers, while watching Donald Trump redefine the presidency in real time.
Obama’s tone was part lecture, part lament, as he ticked off hypothetical scenarios—“Imagine if I had pulled Fox News’ credentials… imagine if I had punished dissenting law firms”—as though to say, “If Trump can do it, why couldn’t I?” But what he’s really saying is something else entirely: He wishes he had. And that’s the most telling part of all.
Because here’s the reality: Trump is doing it. He’s executing policy at a breakneck pace. He’s flipping over every federal table. He’s the guy who doesn’t ask for permission, he just acts—and that, whether his critics admit it or not, is what voters responded to in 2016, again in 2020, and once more in the decisive 2024 comeback.
While Obama was reminiscing about the press corps and cautioning about the “unimaginable,” Trump is, quite literally, pulling federal agencies out by the roots. He’s cutting entire bureaucratic branches. He’s deporting criminal aliens and closing the border.
He’s signing executive orders with one hand and hosting investor roundtables with the other. He’s doing—actually doing—what Republicans have begged their leaders to do for decades. And here’s the kicker: He’s doing it at 4:30 in the morning, without a pause.
Now contrast that with Obama’s time in office. Yes, the Affordable Care Act. But what else? Foreign policy blunders? Spying on reporters? Weaponizing the IRS? A red line in Syria that turned into a dotted one? What Trump’s doing is drawing a hard line not only on policy but on action, visibility, and narrative control. He doesn’t wait for the press to write the story—he is the story, every day, by design.
And you can see the toll that’s taken on Obama’s place in his own party. CNN’s mid-March SSRS poll is damning. Obama, once the party’s undisputed rock star, is now polling behind Hakeem Jeffries and tied with Jasmine Crockett. Crockett, best known for tossing out social media zingers like “skin-folk who ain’t kin-folk,” is now breathing down Obama’s neck as a defining voice for the Democratic base. You can’t make that up.
It’s no wonder Obama sounds like a man filled with regret. Not because he didn’t try hard enough, but because he didn’t push far enough. Because while he was focused on elegance, consensus, and optics, Trump was preparing to bulldoze the whole operation. And now, Trump is the operation.
