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The debate spotlighted Jeb Bush's two big weaknesses — immigration and his brother

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Andrew Prokop is a senior politics correspondent at Vox, covering the White House, elections, and political scandals and investigations. He’s worked at Vox since the site’s launch in 2014, and before that, he worked as a research assistant at the New Yorker’s Washington, DC, bureau.

Midway through the first of what would be several tangles between Jeb Bush and Donald Trump at Wednesday's Republican debate, the billionaire gave the former governor a surprising compliment.

"More energy tonight," Trump said, partially walking back one of his favorite putdowns of Bush. "I like that."

It was true — Bush improved on a truly lackluster first debate performance. He landed some hits on his rivals, touted his record, got some laughs, and even went sorta viral when he admitted having smoked marijuana forty years ago. This will probably be enough to forestall any exodus from donors concerned about his bad recent poll results (for now, at least).

Yet despite Trump's constant needling, a lack of energy was never one of Bush's main problems. Instead, the runaway fundraising leader's candidacy has been dogged by two main issues so far.

First, on immigration, he's both substantively and culturally to the left of a GOP base that hates "amnesty" and has little sympathy for people they deem "illegals." And second, he's unavoidably tied to his brother, who left office unpopular and controversial.

Both of those problems were front and center during the debate.

Trump and Bush faced off on immigration — and it's not clear who won

The disagreement between Donald Trump and Jeb Bush on immigration is partly about policy. Bush wants a path to legal status for 11 million unauthorized immigrants here now, while Trump wants them all deported (though he says he'd let "the good ones" come back). Bush has called unauthorized immigration an "act of love," while Trump argues that "rapists," "drug dealers," and "murderers" are coming across the border.

But immigration isn't just an abstract issue for Bush. He met his wife in Mexico decades ago (she only became a US citizen after their marriage), and he speaks Spanish fluently (calling himself "bicultural").

And though Bush has bragged that these traits will probably help him in the general election, Trump has repeatedly proven willing to cite them in ugly ways to attack him from the right on immigration. "If my wife were from Mexico, I think I would have a soft spot for people from Mexico," Trump said in July. And after Bush told reporters in Spanish this month that Trump wasn't a conservative, the billionaire responded, "He should really set the example by speaking English while in the United States."

During the debate, the CNN moderators brought up both of these comments — and it's not clear who got the better of the exchange.

Bush demanded, and didn't get, an apology from Trump to his wife. Then he defended his policies to the audience: "Are we going to take the Reagan approach, the hopeful optimistic approach, the approach that says that, you come to our country legally, you pursue your dreams with a vengeance, you create opportunities for all of us? Or the Donald Trump approach? The approach that says that everything is bad, that everything is coming to an end."

Trump's response was dripping with disdain — and potentially far more palatable to the GOP right. "Jeb said that they come into our country as an act of love," he snarled. "He's weak on immigration." When moderator Dana Bash asked what was wrong with Bush speaking Spanish, Trump gave the simple answer: "This is a country where people speak English, not Spanish."

In response, Bush again tried to take an inspiring and compassionate approach. "If a high school kid asks me a question in Spanish," he said, "I’m going to show respect and answer that question in Spanish." (Trump accurately pointed out that he had objected to Bush speaking Spanish to a reporter, not a student.)

To national reporters and pundits, Bush seemed to get the better of the exchange. Yet it's worth remembering that Trump has risen to the top of GOP polls partly because of his blunt, offensive rhetoric on immigration — rhetoric not often employed by mainstream Republican politicians, but seemingly popular among the party's base.

Multiple candidates criticized Bush for his brother's record

Meanwhile, throughout Jeb Bush's candidacy, he's been dogged by the problem of how he'll deal with his brother's controversial presidency. And Wednesday night, he faced that challenge again and again.

Moderator Hugh Hewitt brought up the topic — calling it "the biggest elephant in a room full of elephants" — first. "You said you would not be burdened either by your brother or your father’s legacy in the Middle East," Hewitt said. "And then, a week later, you rolled out your list of foreign policy advisers, and it was a lot of the band getting back together again."

In response, Bush argued that "if you're looking at Republican advisers, you have to go to the last two administrations." That's a fair point, but likely one that's not particularly persuasive to a Republican electorate dissatisfied with the establishment and considering outsider candidates.

Later, Donald Trump, Ben Carson, and Rand Paul all openly bragged about how they opposed George W. Bush's Iraq war (though it's not clear Trump opposed the war publicly before the invasion). "It's about judgment," Trump said. "I'm a very militaristic person, but you have to know when to use the military." Bush tried to shoot back, arguing that Trump's past praise of Hillary Clinton demonstrates his own "lack of judgment. "

Trump's response, though, was devastating. "Your brother’s administration gave us Barack Obama, because it was such a disaster, those last three months, that Abraham Lincoln couldn’t have been elected." Bush won some applause by making the dubious point that his brother "kept us safe." But Trump responded, "You feel safe right now? I don't feel so safe."

Rand Paul, too, trashed Bush for refusing to call the Iraq war a mistake back in May. "He said, 'No, we'd do it again,'" Paul said. "We have to learn sometimes the interventions backfire." (Bush made the comments in an interview with Megyn Kelly, but, days later, said he had misheard Kelly's question.)

Later, Cruz trashed "the President Bushes" for appointing David Souter and John Roberts, rather than further-right conservatives, to the Supreme Court. "They weren’t willing to spend political capital to put a strong judicial conservative on the court," Cruz said. Again, Bush was put into the position of defending his brother's judgment in appointing a justice many conservatives now despise for his pro-Obamacare rulings.

Bush likes to make the case that he'll be the strongest general election candidate — indeed, that he's willing to lose the primary so he can win the general. Yet that's a tough case to make when, even among a Republican crowd, he's constantly on the defensive about his brother's record.

And this isn't just about the conservative electorate's seeming interest in new faces. If Americans are faced with the choice between a Clinton and a Bush, which recent presidency are they most likely to feel nostalgic about? If the GOP binds itself to the Bush name yet again, the party would sacrifice the chance to challenge Clinton with a genuinely new face. And that's a problem Bush can't seem to solve.