To win the White House in 2016, Donald Trump first had to get by former Florida Gov. Jeb Bush, the son and brother of two past presidents inextricably linked with U.S. wars in the Middle East.

Attacking the Bush family dynasty — and its legacy — became a feature of Trump’s campaign. And that meant doubling down on criticism of the Iraq War that President George W. Bush had led the United States into under the premise of finding weapons of mass destruction that never materialized.

“The war in Iraq was a big, fat mistake,” Trump responded, when asked at a Republican presidential debate in February 2016 if he still believed, as he said he did in 2008, that Bush should have been impeached for it.

“We can make mistakes,” Trump added. “But that one was a beauty. We should have never been in Iraq.”

The moment was one of many in Trump’s long history of denouncing forever wars and promising, as president himself, to keep the U.S. out of the sorts of foreign entanglements that could lead to them. But one year into his second term, Trump has ordered military action in multiple countries, including the January strike on Venezuela to capture Nicolás Maduro. And now with the war in Iran, Trump has plunged America into its most significant conflict since the post-9/11 wars in Iraq and Afghanistan — without any congressional approval.

“President Trump’s courageous decision to launch Operation Epic Fury is grounded in a truth that presidents for nearly 50 years have been talking about, but no president had the courage to confront: Iran poses a direct and imminent threat to the United States of America and our troops in the Middle East,” White House press secretary Karoline Leavitt said in an emailed statement. “The rogue Iranian Regime under the evil hand of the Ayatollah has killed and maimed thousands of American citizens and soldiers over the years — and that ends with President Trump.”

Trump’s successful 2024 campaign to return to power was predicated in large part on how he hadn’t started any wars in his first term.

“My entire adult lifetime has been shaped by presidents who threw America into unwise wars and failed to win them,” Trump’s future vice president, JD Vance, wrote for The Wall Street Journal in a January 2023 guest column endorsing Trump’s 2024 bid.

“In Mr. Trump’s four years in office, he started no wars despite enormous pressure from his own party and even members of his own administration,” added Vance, an Iraq War veteran. “Not starting wars is perhaps a low bar, but that’s a reflection of the hawkishness of Mr. Trump’s predecessors and the foreign-policy establishment they slavishly followed.”

At a briefing Monday, Defense Secretary Pete Hegseth rejected suggestions that Iran could become Trump’s Iraq, pledging that it would not spiral into an “endless” war. But Trump himself indicated the U.S. could be engaged for longer than he bargained.

“Right from the beginning, we projected four to five weeks,” Trump said at a Medal of Honor ceremony at the White House. “But we have capability to go far longer than that. … Somebody said today, they said, ‘Oh, well, the president wants to do it really quickly, after that, he’ll get bored.’ I don’t get bored. There’s nothing boring about this.”

Trump also listed four objectives for Operation Epic Fury: degrading Iran’s missile capabilities, the destruction of Iran’s navy, ensuring Iran can never obtain a nuclear weapon and containing its proxy forces by ensuring Iran cannot “continue to arm, fund, and direct terrorist armies outside of their borders.”

The beginning of war with Iran comes just weeks after the military operation in Venezuela that ousted Maduro. And Trump said Sunday that he is separately contemplating “a friendly takeover” of Cuba, suggesting that the U.S. could be heavily involved in three foreign entanglements simultaneously.

Though Trump has pledged for years to keep the U.S. out of new wars, he has taken a hard line with Iran, whether by discarding the nuclear treaty negotiated by his predecessor, President Barack Obama, killing Iranian military official Qassem Soleimani in an airstrike or bombing Iran’s nuclear facilities last year.

During his 2016, 2020 and 2024 runs for the White House, Trump said that Iran cannot be allowed to develop a nuclear weapon. Since taking office, Trump has stated “no fewer than 33 times that Iran cannot be allowed to have a nuclear weapon,” a White House official said. That concern that was the basis for launching “major combat operations” against the country, Trump told NBC News on Sunday.

Trump’s skepticism of foreign intervention — and of fighting wars in the Middle East in particular — dates to before his time in elected politics. In addition to describing Bush’s invasion of Iraq as an impeachable offense, Trump had also repeatedly suggested that Obama would use military aggression for political gain.

“In order to get elected, @BarackObama will start a war with Iran,” Trump posted on social media in November 2011.

He made a similar prediction in October 2012, weeks before Obama was re-elected: “Now that Obama’s poll numbers are in tailspin — watch for him to launch a strike in Libya or Iran. He is desperate.”

Trump’s 2016 campaign for president stitched together a new “America First” Republican coalition that rejected the neoconservative, interventionist foreign policy.

“As a candidate for president, I pledged a new approach,” Trump would say in his 2019 State of the Union address. “Great nations do not fight endless wars.”

Jeb Bush, the brother of the president who had launched the Iraq War, made a convenient foil as Trump romped through the primaries during that campaign. Even so, as is often the case with Trump, he had to explain his own shift in thinking on Iraq. When asked by Howard Stern in a 2002 interview if he would support an invasion of Iraq, Trump responded affirmatively. After the audio of the interview resurfaced in 2016, Trump said that he had changed his mind by the time the war began.

“I think that people knew that there were no weapons of mass destruction,” Trump said during a February 2016 appearance on NBC News’ “Meet the Press.” “I think they wanted to go in there, I think they thought it would’ve been easier, they didn’t prosecute the war well.”

Trump’s first term in office was not without occasional military strikes. But as Vance, a Trump critic turned ally, would note years later, there were no new wars on his watch. It was a point of pride Trump and his backers emphasized often.

“Does the USA want to be the Policeman of the Middle East, getting NOTHING but spending precious lives and trillions of dollars protecting others who, in almost all cases, do not appreciate what we are doing? Do we want to be there forever?” Trump wrote on social media in December 2018 after announcing he would pull U.S. troops from Syria and declaring victory over ISIS in a conflict that had begun under Obama.

Trump added: “Time for others to finally fight.”

Days later, during a surprise visit to U.S. troops in Iraq, Trump explained his thinking further.

“While American might can defeat terrorist armies on the battlefield, each nation of the world must decide for itself what kind of future it wants to build for its people, and what kind of sacrifices they are willing to make for their children,” he said. “America shouldn’t be doing the fighting for every nation on Earth [while] not being reimbursed, in many cases, at all.”

The following year, as he was preparing to accelerate the Syria withdrawal amid Turkey’s escalating military operations there, Trump reupped his philosophy.

“Turkey has been planning to attack the Kurds for a long time. They have been fighting forever,” he posted on social media. “We have no soldiers or Military anywhere near the attack area. I am trying to end the ENDLESS WARS.”

And in November 2020, after Trump lost his re-election bid to Joe Biden, acting Defense Secretary Chris Miller issued an update on plans to draw down troops in Afghanistan and Iraq.

“With the blessings of Providence in the coming year, we will finish this generational war, and bring our men and women home,” Miller said. “We will protect our children from the heavy burden and toll of perpetual war.”

Now, though, Trump is openly acknowledging that ground troops might be necessary in Iran.

“I don’t have the yips with respect to boots on the ground — like every president says, ‘There will be no boots on the ground.’ I don’t say it,” Trump told the New York Post in an interview Monday.

So far, six U.S. service members have been killed during the Iran operation.

That’s a far cry from the anti-war posturing from the 2024 campaign that put Trump back in office.

That race began with Vance, then a senator, framing his supportive Wall Street Journal column around the idea that Trump would not “recklessly” send Americans to fight in foreign wars. It ended with a messaging blitz aimed particularly at the young male voters who helped carry Trump and Vance to victory.

In late October 2024, Trump’s team amplified commentary from journalist Peter Hamby, who on CNN had shared that young men he spoke with on college campuses “are worried about global conflict, because they are of draft age.”

And in a series of tweets days before Election Day, longtime Trump adviser Stephen Miller repeatedly warned that a win for the Democratic candidate, then-Vice President Kamala Harris, would lead to young men being “drafted to fight” in a “3rd World War.”

“If you vote for Kamala, Liz Cheney becomes defense secretary,” Miller wrote, referring to the anti-Trump Republican and former House member from Wyoming known for her hawkish foreign policy views. “We invade a dozen countries. Boys in Michigan are drafted to fight boys in the Middle East. Millions die.”