Warning that Trump's reached a 'fork in the road' as Iran war unravels

President Donald Trump is “at a kind of fork in the road” with his war against Iran, a conservative historian explained on Sunday — and the Republican commander-in-chief seems woefully unprepared for it.

“The choice is this: we have now expended a tremendous amount of power to restructure the region,” historian Robert Kagan said on a podcast episode for The Bulwark with conservative commentator William Kristol. “Put simply, that's the goal — restructure the region so that there is no longer an Iranian threat. But there's going to be instability in Iran no matter what happens.”

Kagan argued that even a friendly government in Iran will meet with widespread public resistance. This means there will likely be instability, and the responsibility for confronting that will be placed at Trump’s feet.

“That instability will also create terrorism, brutality, and the potential closure of the Strait of Hormuz,” Kagan said. “It's not as though the region will suddenly become permanently stable. The United States would still have to play a role — but it will have kicked this hornet's nest. It will have upset one balance. So is it going to sustain the other?”

Because of this quandary, Trump must either keep American troops in Iran long-term or withdraw even in the face of likely regional volatility. Kagan argued that the last Republican president to plunge America into an unpopular Middle Eastern war, George W. Bush, did so in Iraq in 2003 — but he at least had a plan.

“To be fair to the Bush administration — and people are now drawing analogies between this and the Iraq War of 2003 — there is a significant difference,” Kagan said. “Whatever else is true, Bush felt responsible for leaving behind a sustainable outcome in Iraq. And if you look at Iraq since the 2003 invasion, there have been six parliamentary elections, seven prime ministers, and a change of government. Iraq has been stable. It hasn't gone to war with anyone. It hasn't committed atrocities against its own people.”

Unfortunately Trump does not appear to feel the same sense of responsibility toward Iran that Bush felt toward Iraq.

“The other day, Lindsey Graham — who is essentially Trump's whisperer on this war, and has openly boasted about his role in pushing Trump toward it — specifically said: ‘I don't believe that if you break it, you own it,’” Kagan said about Graham. “Which means: yes, we can break it and walk away. And I think that is precisely what much of the world expects us to do.”

This is not Kagan’s first time speaking out against Trump. In February, Kagan told CNN journalist Christiane Amanpour that he worries Trump will try to overturn the 2026 midterm elections so he will not lose power.

“I am worried, as I have said and others have been pointing out, about whether we will even have free and fair elections in 2026, let alone in 2028,” Kagan told Amanpour. “I think Trump has a plan to disrupt those elections, and I don't think he's willing to allow Democrats to take control of one or both houses as could happen in a free election.”

Kristol is also an outspoken critic of Trump, such as when he described him as a member of the “Epstein class” in a February editorial for The Bulwark.

“Trump is saddened by any embarrassment to the royal family,” Kristol wrote when Trump said he is “saddened” by the disgrace and arrest of UK prince Andrew Mountbatten-Windsor for his alleged Epstein-related crimes. “And there is no evidence the Trump administration has any interest in seeing justice done, or any intention of having the truth come out. We have an executive branch that is on the side of the Epstein class, not the Epstein survivors.”