Trumpland

Former Trump Official Exposes Humiliating Strategic Error

REALITY CHECK

“Strategically, we seem to be on our back foot,” the ex-Pentagon chief told The Hill.

Donald Trump has recently demanded Iran compensate the U.S. for damages from the “last 50 years”.
KENT NISHIMURA/Kent Nishimura, Getty Images

Donald Trump’s former defense secretary says the president’s war with Iran is not going according to plan.

“Strategically, we seem to be on our back foot right now,” Mark Esper said in an interview with The Hill.

He added that the U.S. military has “imposed a lot of pain” and “done a lot of tactical damage” on the Iranian military.

Former US Secretary of Defense Mark Esper.
Former US Secretary of Defense Mark Esper. Pool/Michael Reynolds, Getty Images

This comes as Trump’s war with Iran has dragged on far longer than he initially anticipated, and he has desperately tried to placate anxieties within his own party ahead of the midterm elections.

Trump has told Americans that the war in Iran is almost over at least 38 times.

JD Vance has offered a somewhat less rosy assessment.

On Saturday, the vice president warned that the conflict is still “in the middle of the game.”

U.S. President Donald Trump speaks to reporters at a briefing on Monday, April 6, 2026 at the White House.
U.S. President Donald Trump speaks to reporters at a briefing on Monday, April 6, 2026 at the White House. The Washington Post/Maxine Wallace, Getty Images

“This thing is not over. It’s obviously not at the beginning,” he told Fox News host Kayleigh McEnany. “We’re applying a whole host of tools, diplomatic, economic, military tools, to ensure that we get the best outcome for the American people.”

The president has escalated demands with the Middle Eastern nation, most recently commanding them to compensate the U.S. “for all of the people that they have killed and gravely wounded with their roadside bombs and many conflicts.”

Donald Trump demands compensation from Iran via Truth Social, August 10, 2026.
Donald Trump demands compensation from Iran via Truth Social, August 10, 2026. @realDonaldTrump / Truth Social

The command comes after Iran’s Supreme National Security Council told the U.S. it must “completely compensate” Iran for damages from the five-month-long war. Trump doubled down, saying Iran needs to pay for damages from the “last 50 years.”

Publicly, Trump has maintained that Iran “is in very bad shape,” but behind closed doors, recent reporting reveals he has accepted that his demands are unachievable.

“Iran’s recent hardline demands for reopening the strait make it increasingly difficult for the president to manufacture a face-saving off-ramp from the conflict,” Mona Yacoubian, director of the Middle East program at the Center for Strategic and International Studies, told The Wall Street Journal.

Recent negotiations with Iran have focused mostly on reopening the Strait of Hormuz, as nuclear negotiations have proven too difficult for the Trump administration to advance.

Instead, Trump is focusing his energy on inflating his image domestically. On Friday, he reposted an article authored by one of his own senior counselors titled “Donald Trump Won The Iran War”.

Donald Trump posts to Truth Social, August 7, 2026.
Donald Trump posts to Truth Social, August 7, 2026. @realDonaldTrump / Truth Social

“It will work out. It always works out. It’s like a chess game,” Trump told Axios on Sunday, of the back-and-forth with Iran.

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