The war in Iraq – the issue that defined George W. Bush’s presidency and haunted candidates from both parties on the 2008 campaign trail – is back. And this time it’s creating headaches for Jeb Bush. In his clearest declaration yet on his feelings about his brother’s invasion of Iraq, the former Florida governor said Thursday that “knowing what we know now, …I would not have engaged.” “I would not have gone into Iraq,” he said. The comments marked the fifth time this week that Bush sought to explain his position on Iraq – a controversy that began Monday with a muddied expression of support for the war. Bush later tried to clean up the mess by calling the query – one many believe he should have anticipated – a “hypothetical,” and by Wednesday, he acknowledged he would have done things differently in Iraq. On Thursday, Bush argued that the invasion – though perhaps inspired by faulty intelligence – had been beneficial, saying the world was “significantly safer” without Saddam Hussein in power. The clumsy responses have surprised his allies and could reinforce concerns that Bush, who hasn’t run for public office in more than a decade, is a rusty campaigner ill-equipped for the fast-moving news cycles of the social media age. It also revealed the difficulty Bush faces in presenting himself as his “own man” unburdened by his brother’s controversial foreign policy decisions. RELATED: Student confronts Jeb Bush on ISIS WATCH: The Bush family and Iraq “The question about Iraq is not an illegitimate, hypothetical question. If you’re sitting around pondering a Jeb Bush candidacy, it’s the first obvious question that you have to be able to answer,” said GOP strategist Steve Schmidt, who helped John McCain craft his message on Iraq during the 2008 election. “What his answer shows is the difficulty in moving beyond the Bush foreign policy in order to be able to attack the Obama-Clinton foreign policy, and to offer a vision for moving the country on to a firmer security footing.” The issue has become a significant distraction for Bush as he tours the nation ahead of a potential White House bid. One Wednesday night, Bush found himself defending his brother’s policies after a college student confronted him in Nevada. “Your brother created ISIS,” she told him during an accusatory exchange on the current situation in the Middle East. Bush’s Republican rivals pounced at the opening. ‘Really important question’ “I think it’s a really important question, and I don’t think it’s just hypothetical,” Kentucky Sen. Rand Paul, a GOP presidential hopeful, told CNN’s Wolf Blitzer Wednesday. “I think even at the time invading Iraq was a mistake.” New Jersey Gov. Chris Christie noted he had no trouble answering the question directly and told CNN’s Jake Tapper that in light of intelligence showing Iraq did not have weapons of mass destruction, he would not have gone to war. Ohio Gov. John Kasich took a similar stance in an interview with an Ohio newspaper. Two GOP bundlers who couldn’t speak with attribution because they are raising money for Bush said it was unnerving to see their candidate so prone to gaffes. Still, they shrugged it off as part of the campaign process. READ: Jeb: George W. Bush is a top foreign policy adviser While it has been a tough week for Bush, the return of the Iraq debate is also a reminder that the war perhaps looms even larger for Democratic frontrunner Hillary Clinton. Of all the candidates contemplating a presidential run, she is the only one in the field who has cast a vote to authorize military action in Iraq. Some Democratic voters still have not forgiven her for the vote – cast when she served as a senator from New York – which was a significant factor in her loss to Barack Obama during the 2008 Democratic presidential primaries. “I thought I had acted in good faith and made the best decision I could with the information I had,” Clinton, a former secretary of state, wrote in her book “Hard Choices.” “And I wasn’t alone in getting it wrong. But I still got it wrong.” Still, Clinton has not addressed her vote on Iraq since announcing her presidential bid, whereas Bush spent much of this week in the awkward position of having to clarify his views. ‘Different decisions’ He went a step further at a political event in Nevada on Wednesday, saying, “given the power of looking back and having that, of course anybody would have made different decisions. There’s no denying that.” He did not go so far as to say the war was a mistake, arguing that hypothetical questions about what he would have done are a disservice to the soldiers that fought and died in the conflict. With months to go before GOP voters cast their first ballots in the early nominating contests, it’s not clear that any of Bush’s early stumbles will leave lasting damage. “If you’re going to make (mistakes) – make them nine months out,” said Tom Rath, a New Hampshire political operative who isn’t aligned with a candidate. “I don’t know that his position in the field has been impacted by this, but he was playing defense.” But Craig Robinson, a GOP activist who founded The Iowa Republican, said the flap over Bush’s Iraq comments could further weaken his standing among GOP voters in the Hawkeye State – not only because they raised questions about his polish as a candidate, but because they also created confusion about how his foreign policy approach would differ from his brother’s. Bush’s original comment “resurrected the debate on Iraq, which is a losing argument,” Robinson said. “His refusal now to answer any similar questions after he claims to have misheard the original questions is even worse,” Robinson said. “Nobody wants to go back and litigate war in Iraq, even now as the GOP is very hawkish when it comes to foreign policy. The problem with Jeb’s answer, and now non-answer, is that we are left to wonder what his foreign policy would be if elected president.” While the war in Iraq was unpopular with the American public – 75% said it was not “worth the loss of American lives and other costs,” in a June 2014 CBS News/New York Times poll – the conversation surrounding that corner of the globe has moved beyond the invasion in recent years. At Bush’s political event in Nevada Wednesday, the first question was not about the war that was launched more than a decade ago, but rather the rise of the Islamic State militant group. READ: Jeb Bush tries to move past Iraq questions “What happened in 2003 is not a subject of a policy debate that affects what the U.S. is doing in Iraq today and what the U.S. will be doing in Iraq tomorrow,” said Anthony Cordesman, an expert on security and Middle East policy at the Center for Strategic and International Studies. “The world is a very different place.” The discussion surrounding Iraq has evolved to include the fight against ISIS and broader sectarian, political and economic instability, he said. “If Bush had been a little more articulate, people would’ve picked up on the fact that he was making that point,” Cordesman said. But “if he can’t rise above this issue, he hasn’t got a prayer anyway.” The confrontation with the college student in Nevada about ISIS resulted in a new riff on him defending his brother’s foreign policy. “When we left Iraq, security had been arranged, Al Qaeda had been taken out. There was a fragile system that could have been brought up to eliminate the sectarian violence,” he said, arguing that the rise of ISIS was President Obama’s fault, not his brothers.