Jeb Bush’s last name comes with advantages that are difficult to overstate. In a presidential race, he gets, among other things, instant name recognition and a built-in fundraising apparatus from his father and brother. Those assets alone explain why a man who hasn’t won an election in more than a decade is nonetheless considered a serious contender for his party’s presidential nomination.

And yet, a few months into the presidential race, Bush has not been able to turn “contender” into “front-runner,” in part because he cannot seem to escape the legacy of the same last name that provides him so many privileges.

Bush’s struggle with the Bush legacy started in February, when the former Florida governor gave a speech declaring: “I love my father and my brother. I admire their service to the nation and the difficult decisions they had to make. But I am my own man.” There was no problem with the rhetoric, except for the fact that it was accompanied by Bush announcing his foreign policy advisers — 19 of 21 of which had formerly worked for his father or brother. A few months later, Jeb Bush said his brother was one of his top advisers on the Middle East.

George W. Bush’s policy in that region soon became a focus of inquiry on the campaign trail. In May, Fox News’ Megyn Kelly asked Jeb Bush: “Knowing what we know now, would you have authorized the (Iraq) invasion?”

Bush declared, “I would have” and insisted “so would almost everybody that was confronted with the intelligence they got” — somehow ignoring 133 House members and 23 senators who saw some of that intelligence and voted against the war. But that wasn’t the only thing Bush said: He went on to proudly assert that when it came to the decision to invade Iraq, “news flash to the world, if they’re trying to find places where there’s big space between me and my brother, this might not be one of those.”

Bush later tried to walk back his comments and distance himself from his brother’s Iraq policy, but the political damage had already been done. As conservative talk show host Laura Ingraham put it: “You can’t think going into Iraq now, as a sane human being, was the right thing to do. That’s like you have no ability to learn from past mistakes at all.”

Recently, Bush faced another test of whether he could be “his own man” and honestly assess his brother’s legacy. In an appearance on CBS’s “Face the Nation,” he was asked by host Bob Schieffer to provide his views on the “successes and mistakes” of the George W. Bush administration. Jeb Bush said “the successes clearly are protecting the homeland” and he asserted that his brother “kept us safe.”

Of course, George W. Bush was president on Sept. 11, 2001 — a day that America was not “kept safe.” George W. Bush was also president in the months leading up to that catastrophic attack — the same months in which he was given a memo headlined “Bin Laden Determined to Strike In U.S.” And as MSNBC’s Steve Benen argues, even if you somehow pretend George W. Bush only became president on Sept.12, 2001, the whole “kept us safe” idea is questionable at best.

“Shortly after 9/11, for example, there were deadly anthrax attacks,” Benen wrote this week. “There were scores of terrorist attacks against U.S. troops in Iraq and Afghanistan. There was an increase in the number of terrorist attacks on U.S. diplomatic outposts around the world.”

Jeb Bush will no doubt have more opportunities to try to distinguish himself from his family members. If he can’t, though, even the enormous advantages that come with his last name might not be enough to carry him to victory.

David Sirota is a syndicated columnist and author. Email him at: ds@davidsirota.com; follow him on Twitter @davidsirota; or visit his website at: www.davidsirota.com.

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