Deanna Dent / Reuters

Jeb Bush had a very bad few days last week. They won’t be the last bad days of this campaign. The Iraq question hasn’t been settled and won’t go away. And other questions as awkward and difficult are waiting to be asked.

Bush’s ability to raise large amounts of money has distracted attention from the inherent fragility of his campaign. But there are many reasons to be skeptical of his ability to secure the Republican nomination, much less win the White House, and the early months of his undeclared campaign have done little to dispel those doubts. Here are six:

Tainted Brand

George W. Bush’s popularity has recovered somewhat since he left office. (Thirteen years ago, when he was president, I wrote speeches for him. Now, I write for a magazine.) At the end of 2014, more Americans had a positive than a negative image of him for the first time since 2005. But then, the same is true for Jimmy Carter—rather more so actually. Once an unpopular president has departed office, the defeats and disappointments of his tenure vanish into American amnesia. But that amnesia is highly conditional on the ex-president and his namesakes staying away from politics.

Bobby Kennedy could credibly seek the presidency in 1968 because so many Americans loved his martyred brother. Franklin Roosevelt shared a name with a hugely popular cousin. Even defeated one-term presidents can boost a relative if they remain popular within their party: Robert Alfonso Taft could plausibly aspire to follow the lead of his father, William Howard Taft; George W. Bush did follow George H.W. Bush. But none of Herbert Hoover’s relatives have run for high office. Subsequent James Earl Carters have likewise pursued other endeavors. There have been no more new Nixons—and Nixon resigned from office only 1 point less popular than George W. Bush in October, 2008.

Self-Refuting Message

Jeb Bush has named his PAC “Right to Rise.” He has expressed concern about the hardening of class lines and the concentration of hereditary advantage among an elite few. "How do we restore America's faith in the moral promise of our great nation that any child born today can reach further than their parents?” Jeb Bush asked in a speech in Detroit in February, 2015. This message might resonate at a time when so many doubt that a person can start poor in America, work hard, and become rich. But could there possibly be a worse messenger: a man born at the top, who has vaulted into the front rank of the 2016 race thanks—not to any widespread excitement over his candidacy—but to his family’s unrivaled fundraising operation, developed over three generations at the highest levels of national politics?

A Candidate Who Can’t Attack His Opponent

Barring some rip in the space-time continuum, Hillary Clinton will be the Democratic nominee in 2016. She should be an easy target! But the one Republican least able to attack her is Jeb Bush, who shares almost every one of her vulnerabilities: Yesterday’s politics? Dynastic entitlement? The use of political connection for financial advantage? Jeb Bush will want to talk about none of those things. The explanation will be given that he wants to run a “positive campaign.” The reality will be a tacit pact to avoid awkward topics, a pact to which a less vulnerable Republican would not have to accede. And while a positive campaign sounds like a welcome development, it will bump into another reality …

The Wrong Kind of Moderate

Jeb Bush appeals to the more moderate-Republican voter. A mischievous survey by the Democratic firm Public Policy Polling found that Scott Walker led among Republicans who believed that the federal government was plotting a military takeover of Texas, while Jeb Bush led among those who did not. This is the kind of data that might normally be filed under, “Ask a silly question …” Still, it indicates something about where the different candidates find their support. But as Jeb Bush himself will insist, moderation in tone is not the same as moderation in content. "“I’m not angry. I’m not trying to divide, I’m trying to persuade. Perhaps moderate in tone is misinterpreted as moderate in beliefs,” he told Maggie Haberman of The New York Times. After the jolt of the 2012 defeat, some Republicans began to talk about modulating the “makers versus takers” approach of Mitt Romney and Paul Ryan and their brain trust, and developing a platform more congenial to the middle class. But parties allow their aspiring leaders only so many deviations, and Jeb Bush has exhausted his heterodoxy budget on immigration and the Common Core curriculum. On economic issues, he will not have scope for innovation.

And there’s little sign that he has any appetite for it. He has released few specifics on economic questions. In the past, he’s indicated that he might be willing to exchange deficit-reducing tax increases for spending cuts. But all the early indications suggest that his offer to the middle class won’t improve much on Romney’s: big tax cuts aimed at the highest earners, less healthcare coverage, and entitlement cuts.

Many in the media will describe a more pro-immigration stand as “moderate,” because they associate it with acceptance of ethnic diversity. Such a stand, however, can also be consistent with a candidate’s comfort with concentrated wealth and accelerating inequality. If that’s moderation, it’s not the kind of moderation the country is yearning for.

A Candidate of Ideas Afraid to Discuss Them

As governor of Florida, Jeb Bush immersed himself in policy details. Since leaving office, Jeb Bush has consumed policy literature and talked with the conservative world’s intellectual luminaries. "Those who have hashed over policy and politics with Mr. Bush,” a New York Times profile reported, “describe him as a conservative animated less by rigid ideology than a technocrat’s quest to identify which solutions work best.” The book on immigration policy cosigned by Jeb Bush and his friend Clint Bolick is detailed and substantive. The nearer Jeb Bush approaches the presidential race, however, the more cautious his remarks have become. His party mistrusts him on immigration and curriculum, and so he must appease it on everything else. But if Jeb Bush won’t or can’t offer new ideas, what will he offer instead? His record as governor of Florida, more than a decade ago, during the biggest real-estate boom since the 1920s? His not-exactly-rags-to-riches life story? What?

Return of the Soap Opera

Barack Obama drew considerable support in 2008 from Democrats weary of the turmoil that seemed always to envelop Bill and Hillary Clinton. “No drama Obama,” was both a personal compliment and a public commitment. Now the Clintons have returned. And the question for Republicans is: Do they want to book-end the Clinton family soap opera with their own Republican psychodrama? Why after all is Jeb running? If George W. ran to avenge a father’s defeat, what now motivates the younger brother to seek to succeed the elder? Rivalry? Unfinished business? A feeling of family claim to the office? Those are unanswerable questions of course. That won’t stop thousands of commentators from filling the public air with their attempts. And every second devoted to the question, “What’s up with these Bushes?” is a second that not only diverts attention from its counterpart, “What’s up with these Clintons?”—but also normalizes the un-republican (small “r”) shock and weirdness of what the Clintons are trying to do.

“It’s rather like watching the Borgia brothers take over a respectable North Italian town,” Harold MacMillan reportedly observed, as the Kennedys arrived in Washington. That applies equally well to the Clinton family and its intricate manipulation of power to acquire wealth, and then of wealth to acquire a second lease on power. “Everybody does it” has always been a preferred Clinton line of defense for whatever they get up to. If the Republicans choose Jeb in 2016, they’ll validate that defense in the most spectacular possible way.

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