Liberal pundit Roger Simon was aiming for a cheap laugh when he wondered whether Jeb Bush had been “dropped on his head as a child” in a Politico piece in which he skewered the presidential contender for comments made last week about Iraq and other remarks in which he said his elder brother George would be his top adviser on the Middle East. According to Simon and most of the left, the only thing for which George W. Bush should be remembered is a disastrous war in Iraq. But even for those who don’t view things from the same partisan liberal perspective as Simon, Jeb got himself in trouble by defending the decision to invade Iraq. That since-corrected statement can be defended as can the notion of W being a good man to have as an adviser on U.S.-Israel relations. But the problem for Jeb isn’t that what he said about Iraq and foreign policy isn’t entirely or even mostly wrong. It’s not. The catch is that this exchange reminds Republicans of the two major reasons why nominating Jeb may not be such a hot idea: the dynasty problem and the fact that it would give Democrats a chance to run again against the former president rather than having to defend the records of Barack Obama or Hillary Clinton.

Let’s specify first that Jeb clearly blundered when asked by Megyn Kelly whether, given everything we know now, whether he would support the invasion of Iraq. Instead of acknowledging the mistakes that were made and the fact that weapons of mass destruction weren’t found, Bush answered a different question. He said that placed in that moment again with what he knew then, he would still have backed the idea and that Hillary Clinton (who voted for the war and defended it for years until it became too unpopular to do so) would have too. He’s right that most leading figures in both parties supported the war at the time. It’s also both unfair and untrue to claim that the Bush administration lied about the intelligence or that they cooked it to justify their goals.

Moreover, Jeb was right to note that the surge ordered by his brother in 2007 retrieved a dangerous situation. The sign of a true leader is the ability to admit a mistake and then change course to achieve the objective, something our current president is incapable of doing. When W left office in January 2009, Iraq was a war that had been won, something that the Obama administration acknowledged. If Iraq is back to being a disaster today, it’s solely the fault of President Obama whose decisions led to a wrongheaded evacuation of American troops that created the vacuum into which ISIS moved in recent years.

Let’s also acknowledge that contrary to Simon’s snark, George W. Bush is a good suggestion for someone to consult with about the U.S.-Israel alliance. When Obama came into office he said the reason for the stalemate in the Middle East was that Bush was too close to Israel. By establishing more daylight between Israel and the United States he thought he could achieve peace. But six years of constant fights with Israel that have led to open threats about the administration abandoning Israel at the United Nations haven’t brought us closer to peace. To the contrary, the daylight Obama sought encouraged more violence and Palestinian intransigence. More importantly, Obama’s decision to try for détente with Iran has alienating all of America’s allies in the region, the Arab states as well as Israel. For all of the abuse hurled at W from the left, the Middle East he left us looks pretty good in comparison to the chaos Obama has enabled.

But even if everything Jeb said about his brother is true, and most of it is, that doesn’t really help his cause.

The isolationist moment in American politics that seemed to give Senator Rand Paul a shot at the nomination has passed. Support for a foreign policy that seeks to exert American influence and defend its interests is important to most Republican primary voters and Bush has certainly articulated well thought out positions that will win him votes. But though a lot of Republicans are happy to defend the honor of W or even Dick Cheney against leftist slanders, that isn’t really the conversation anyone in the GOP wants to have right now.

To be fair to Jeb, it’s not as if he has gone out of his way to start this discussion. The comments about W and Israel were generated by the anger among many members of the pro-Israel community (and not just the billionaire that owns casinos) about former Secretary of State James Baker’s attacks on the Jewish state. The longtime faithful Bush family retainer is listed as one of Jeb’s advisers. Bringing up W was the only way he had of disassociating himself from Baker without actually throwing him under the bus.

But bearing the Bush family name brings with it clear disadvantages as well as benefits. Republicans know they’ll be better off nominating someone from a more humble background who can’t, as Mitt Romney was, be portrayed as a heartless plutocrat. Just as Hillary will carry around a lot of negative baggage, Jeb can’t escape the tired, old and deeply destructive arguments about Iraq. He may be a candidate who brings experience as a governor and well considered policy positions on both domestic and foreign issues. He’s also shown a willingness to and avoid flip-flopping even if it means daring the base to oppose him on immigration and the Common Core education standards. That illustrates character if not always the best political judgment.

But his greatest problem remains the challenge of trying to be the third president Bush. It’s certainly possible for him to overcome that obstacle. But whether or not it is fair, this latest kerfuffle illustrates how great the burden that W’s record will be for Jeb.