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Jeb Bush, who plans to announce his presidential candidacy on Monday, during a television interview this month in Orlando, Fla. CreditJoe Raedle/Getty Images 
WASHINGTON —  Jeb Bush had a plan for the last six months he spent as an unannounced candidate for president. He would raise tens of millions of dollars, distinguish himself from his brother’s controversial presidency, start winning over conservatives and establish himself as the Republican to beat for his party’s nomination.
Other than raising the money, little has gone as he had hoped. He has been torn between defending and distancing himself from George W. Bush, been unable to assuage party activists uneasy with his immigration and education views, and run into a wall of opposition on the right. And now, as he prepares to make his candidacy official on Monday, Mr. Bush finds himself in a position he could not have imagined: Part of a pack of candidates, and the target of questions about his own competence and conservatism.
Frustrated, according to his associates, by elements of his political operation and performance so far, he appointed a new campaign managerlast week who is preparing an aggressive new approach to the race. Yet Mr. Bush still faces fundamental challenges in appealing to a Republican primary electorate that is much different from the one his father or even his brother faced — a party no longer willing to automatically anoint the pragmatic, well-financed, establishment-aligned candidate that the Bush name personifies.
“He just hasn’t met the expectation level of what we expected of a Bush,” said Senator John McCain, Republican of Arizona, who is supporting Senator Lindsey Graham’s candidacy but likes Mr. Bush. “And that’s been a hindrance to him.”
While Mr. Bush knows he has to change course in some ways, he also does not want to overreact and risk losing the image of a calm, seasoned leader that he has sought to project, according to several advisers and associates, who spoke on the condition of anonymity to describe campaign discussions and strategy. They say Mr. Bush, having watched negative stories pile up while he focused on fund-raising in recent months, wants to move quickly to campaign with voters — especially in New Hampshire, which he increasingly considers a must-win primary state.
He is also determined not to change his positions on immigration and education, which many Republicans loathe; his best alternative, he believes, is to use his record in Florida to appeal to a party that has become more conservative since his father and brother were president.
“There’s a bias against him — that he’s another Bush, that somehow he’s a moderate — that isn’t fair and that he has to work to overcome,” said Andrew H. Card Jr., a Bush family friend who was White House chief of staff for Mr. Bush’s brother George W. Bush and transportation secretary for their father. “The key thing is he will have the financial resources, and the political maturity, to take the time to try to win people over.”
Mr. Bush’s political instincts have also been a problem. Advisers say his self-certainty and nine years out of politics have caused him to act as his own best adviser. The consequences were evident in his refusal for days to give a straightforward answer about whether he would have authorized the invasion of Iraq in 2003. Only after advisers convinced Mr. Bush that he was damaging himself did he say he would not have gone into Iraq.
“There’s a little bit of rust on him,” said Bob Martinez, a former Florida governor who is now raising money for Mr. Bush. “He’s still finding his rhythms.”
The reshuffled campaign team is aiming to hone Mr. Bush’s abilities as a candidate while sharpening its tactics against Republican opponents. Mr. Bush’s new campaign manager, Danny Diaz, is widely known in Republican circles as a hard-edge operative who is driven by trying to dominate daily news coverage with his candidate’s message or his rivals’ weaknesses. (The previous manager, David Kochel, is known as more cerebral.)
Mr. Diaz, who seared John Kerry in 2004 and Mr. Romney in 2007 with charges of flip-flopping on issues, and other Bush aides are determined to develop new lines of attack against Senator Marco Rubio of Florida and Gov. Scott Walker of Wisconsin, the two Republicans who represent the greatest threats to Mr. Bush’s nomination, according to his advisers and allies.
The Bush campaign sees Mr. Rubio as vulnerable on his Senate record, which is short on legislative success and includes shifts on immigration, and on his history of managing his finances. And they regard Mr. Walker, too, as susceptible to attack on issues on which he has changed his positions, according to the advisers. By hiring Mr. Diaz, Mr. Bush wanted to send a clear signal that “the culture of the Bush operation will now be a Pickett’s Charge engagement campaign with his main opponents,” according to one Bush ally.
It is a far cry from campaigning “joyfully,” as he mused about doing last year. Instead of sparring from afar with Hillary Rodham Clinton this week, when the two candidates widely considered their party’s favorites embark on separate announcement tours, Mr. Bush finds himself behind in early Iowa polls and grouped with other Republicans barely in double digits in New Hampshire.
Mr. Bush’s aides and supporters concede that by spending the first half of 2015 focused more on banking money for his “super PAC” than offering a policy vision, he risked his early standing. But it was worth doing, they argued, because so few voters are closely following the race and because Mr. Bush’s team is expected to announce a huge fund-raising sum in July that will far outstrip his rivals and, they hope, give him momentum. This money is intended partly to give him a big advantage on the airwaves in the weeks before and during the burst of primaries and caucuses in March.
“They set really high fund-raising goals, and as a result he’s been doing the bare minimum on the political front, so now he really needs to start winning more people over,” said Jim Towey, a close friend of Mr. Bush and an official in his brother’s administration.
Before George W. Bush, the governor of Texas at the time, even officially entered the race in June 1999, over half of the House Republican caucus, 114 of 222 Republican members, endorsed his candidacy. “There was no Tea Party back then,” said a former Texas congressman, Henry Bonilla, one of George W. Bush’s early presidential supporters. “Now you’ve got a lot of splits within the family and a huge list of candidates scratching and clawing for support. It’s a completely different world.”
Jeb Bush will formally begin his candidacy with about two-dozen House members committed to him, not all of them publicly, according to Bush advisers briefed on the endorsements. Mr. Bush does not have a single public endorsement in the Senate — where four Republicans are also running for president — but supporters say a handful of establishment-aligned senators are privately supportive.
But many Republican voters have made clear that they oppose Mr. Bush’s relatively centrist positions on overhauling immigration and education. By standing his ground — rather than opening himself up to the flip-flopping charges that his aides intend to aim at Mr. Walker — Mr. Bush has imperiled his prospects in the conservative-dominated Iowa caucuses, which begin the nominating process.
While Mr. Bush intends to compete there, his posture has only heightened the importance of the New Hampshire primary, which also illustrates the challenges posed by the growing field. Not only are several candidates seeking votes on Mr. Bush’s right, but he also could find competition for support from center-right Republicans and unaffiliated voters from the likes of Gov. Chris Christie of New Jersey, Gov. John R. Kasich of Ohio and Mr. Graham, each of whom eyes New Hampshire as a springboard.
“He had a chance to knock a lot of people out,” Mr. Graham said of Mr. Bush, “and he missed that chance.”
If Mr. Bush is facing ferocious conservative headwinds, he is still not ready to radically recalibrate his message. In his kickoff speech on Monday at a Miami-area community college, Mr. Bush is set to extol an aspirational and inclusive brand of conservative politics, make the case for projecting American power abroad, criticize Mrs. Clinton — who gave the kickoff speech of her presidential campaign on Saturday — and recount his accomplishments as Florida governor to highlight the paucity of what he believes are needed improvements in Washington.
Florida offers Mr. Bush the chance to go on the offensive against less-credentialed rivals and employ the conservative policies he enacted in state government as a defense against charges that he is insufficiently conservative. Florida is critical to Mr. Bush for another reason: He believes that whoever loses the shared home state primary — he or Mr. Rubio — is not likely to recover.
But advisers and allies of Mr. Bush believe that the race has only just begun and that Mr. Bush will have the money and a set of strong performances in the televised debates (or so they hope) to help him in the long fight for the nomination.