Are the neoconservatives turning on Jeb Bush? It would be ironic, considering the men his brother turned to for foreign policy advice. It would also be highly problematic—since foreign policy establishment hawks should represent one of Bush’s few natural constituencies on the right. But it’s hard to observe recent developments and not suspect something is afoot.

I’ve often observed that Sen. Rand Paul has to walk a fine line in order to keep all the disparate elements of his coalition together, but it’s increasingly looking like Jeb Bush is having to do the same thing. He has the legacies of his father and brother to contend with. And while these legacies aren’t necessarily mutually exclusive, they aren’t necessarily complementary, either. And therein lies the trap for Jeb: Does he alienate the GOP’s main cadre of foreign policy activists and thinkers, or does he saddle up with them and risk being seen as the second coming of his brother?

The foreign policy “realist” community hopes Jeb will be the “smart” son and follow the “prudent” footsteps of his father. Bush 41 oversaw the collapse of the Soviet Union and liberated Kuwait without toppling Saddam, a move that—depending on where you stand—was either an example of prudence or cowardice. But neoconservatives prefer George W. Bush’s more aggressive foreign policy, and want the GOP to nominate a hawk in 2016. Now Jeb Bush’s campaign needs to figure out what kind of President Bush he would be, and he likely won’t be able to assuage the concerns of both camps.

The conundrum, presumably, began when Jeb announced his foreign policy team. Much was made of the fact that many of his advisers had served in previous Bush administrations. This was much ado about nothing. Any Republican who gained senior foreign policy experience in the last quarter of a century would likely have worked for a Bush administration.

More interesting was the amount of daylight between the foreign policy advisers who served his father and his brother—a cleavage that is especially noteworthy in the context of the larger discussion taking place right now, regarding Iran and Israel. There’s a lot of range between the neoconservative Paul Wolfowitz and an old-school GOP realist like James Baker, yet both are on the list of Jeb advisers.

Speaking of Baker, the Washington Free Beacon, which is widely thought of as a neoconservative outlet, recently noted: “Jeb Bush’s selection of Baker as a foreign policy adviser has sparked concern among conservatives and in the Jewish and pro-Israel communities. Baker is infamous for his hostility to Israel, having said during his tenure as secretary of state in the George H.W. Bush administration, ‘F--k the Jews, they don’t vote for us anyway.’ Baker is also a supporter of President Obama’s Iran negotiations.”

As the Free Beacon expected, Baker—who served as Secretary of State during George H.W. Bush’s administration—did not go easy on Israel when he addressed the liberal J Street conference. And this has led to some think that Jeb Bush might seek to follow his father’s foreign policy—not his brother’s.

In a world where Republicans are trying to out-hawk one another, this might sound absurd. But presidents have been known to govern differently from the way they campaign—remember in 2000 when Bush ran as the anti-“nation building” candidate? “The older Bush circle seems confident that Jeb sided with his father and Brent Scowcroft on the folly of letting the neocons push America into diverting from Osama to Saddam,” wrote Maureen Dowd. (It should be noted that Scowcroft penned a 2002 Wall Street Journal op-ed titled “Don’t Attack Saddam,” which was eerily prescient in many regards.)

Some are clearly worried that Dowd is right—that Jeb is a chip off the old block. “Whether Jeb disavows James Baker, & how quickly & strongly, could be an oddly important early moment in GOP race,” Bill Kristol tweeted (linking to a Politico story about Baker blasting Bibi). This isn’t an anomaly. The Washington Post’s Jennifer Rubin writes that a source at a Jewish organization told her: “Jim Baker’s bitterly critical comments of Israel and Netanyahu conjured up the worst memories of the H. W. Bush administration’s confrontation with the Jewish state. Any 2016 campaign that takes advice and counsel from him will raise serious questions and concerns from the pro-Israel community.”

The comparatively moderate, intellectually inclined Jeb Bush would seem like a natural candidate for neoconservatives to rally behind. But Baker speaking at J Street while working for the campaign in some capacity is cause for concern. This is dangerous if prominent hawks start to suspect that Jeb might not be as friendly to their cause as the Ted Cruzes of the world. Kristol and Rubin would seem to be sending a message to Bush that he can’t take their support for granted. They need him to prove that he’s a lot more like Dubya than his dad. Given Jeb’s vulnerabilities with so much of the rest of the conservative coalition, they’re in a good position to make demands. And he’s not in a good position to deny them.

Politico is already reporting that Jeb Bush is distancing himself from Baker, noting that he “disagrees” with him on Israel. And writing at National Review Wednesday morning, Jeb made his pro-Israel position clear. Let’s see if that’s enough for the critics. If Jeb really wants to win the nomination, he might have to drop Jim Baker like a bad habit.