Two reasons why: (1) He thought that he'd have an enormous pile of money that would deter any other 'Pubbie from daring to challenge him; and (2) he actually thought that his surname would be an asset:
The airport huddles were just one sign among many of a political operation going off course — disjointed in message and approach, torn between factions and more haphazard than it appeared on the surface. Bush’s first six months as an all-but-declared candidate have been defined by a series of miscalculations, leaving his standing considerably diminished ahead of his formal entry into the race on Monday.
In interviews this week, dozens of Bush backers and informed Republicans — most of whom spoke on the condition of anonymity in order to comment candidly — described an overly optimistic, even haughty exploratory operation. Strategic errors were exacerbated by unexpected stumbles by the would-be candidate and internal strife within his team, culminating in a staff shake-up this week…
IOW, Jeb thought that being Bush III would be enough, so much so that he could make infuriating the GOP's conservative base the centerpiece of his campaign and still easily get nominated because of it:
On the stump, Bush has stuck to his pledge not to shift to the right to win the nomination, but his middle-of-the-road positions on immigration and education have come off more as out of step with the base of his party than shrewdly pragmatic. His wonky question-and-answer exchanges with voters sometimes resemble college lectures rather than a disarming appeal for votes…
IOW, he's almost as godawful a retail politician as....Hillary Clinton. No wonder he hung a medal around her jowly neck.
“We’ve learned that the prospect of a big financial advantage is not going to keep people out of the race and that the notion of a new face is stronger than we might have thought,” Vin Weber, an outside Bush adviser, said in an interview. “That requires modest adjustments in strategy, not wholesale changes.”
Which tells me that they haven't learned a damn thing. Most especially that anybody named "Bush" is dead meat from the starting gate. Jeb could be given unlimited access to Federal Reserve printing presses and he couldn't amass enough money to overcome his family and its utterly radioactive "brand". We, the grassroots, have plainly and simply had enough of House Bush and we want no more of it. Period. EVER.
Plus, it's even worse for Jeb, because unlike his pop and big bro, he is facing a top-flight, capable, and aggressive field of challengers. Scott Walker, Ted Cruz, Marco Rubio, Chris Christie, etc., etc., etc. are one helluva lot more formidable than Bob Dole (1988) and John McCain (2000) ever were. Even worse for Jeb, Dole and McCain, respectively, positioned themselves to Bush41's and Bush43's left, leaving the latter the de facto "conservatives" in those nomination races in addition to being the "establishment" candidates. But Jeb is not only facing a number of formidable conservative challengers, he's going out of his way to stay well to their left, almost as if he's already making plans to take the expected dive to Mrs. Clinton next November.
Yet the Bush III campaign can't understand why Jeb has not only not taken off, but isn't making this race a wire-to-wire laugher. And they think all that's needed is "modest adjustments" and, of course, more money.
I remain to be convinced that the absurdly overcrowd conservative field won't collapse the proverbial bed and hand Jeb the nomination in just the walkover the latter is expecting. But the degree of difficulty of that self-defeating task will be the highest it's ever been.
UPDATE: By the way, if Vin Weber is monitoring us, this is not going to help:
Republican presidential contender Jeb Bush says his views toward single mothers "have evolved" since he suggested twenty years ago that they were becoming too accepted by society.
In a 1996 book, Bush and co-author Brian Yablonski expressed concern about changing cultural mores and wrote, regarding unwed motherhood, that there was "no longer a stigma attached to this behavior." This was in a chapter titled "The Restoration of Shame."
Visiting Poland on Thursday, Bush told reporters his book, Profiles in Character, was a policy piece on cultural indicators and, despite its tone on single mothers, the focus was more on holding fathers accountable.
"My views have evolved over time, but my views about the importance of dads being involved in the lives of their children hasn't changed at all," he said.
Exit question: How long until Jeb plays the Bruce Jenner card and enters the race as "Caitlyn Bush"?
What? What's that? That's Debbie Wasserman Schultz?
Sorry. But you have to admit, it was an easy mistake to make.