© Mark Foley/Associated Press Gov. Jeb Bush of Florida met in January 2000 with State Representative Anthony C. Hill and State Senator Kendrick Meek.

In 1999, shortly after Jeb Bush’s election as governor of Florida, the leader of a national movement to overturn affirmative action policies visited his Tallahassee office with a request: Would Mr. Bush support a ballot measure banishing such policies, which had become a favored conservative target?

The governor’s eyes wandered to an image on his wall, featuring several black children. He approached the photograph. “I’m not with you,” Mr. Bush said finally, according to the activist, Ward Connerly. “They are the ones I want to help.”

By the end of the year, black leaders across Florida disagreed with that self-assessment.

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Mr. Bush unveiled an alternative plan, which itself took aim at racial preferences in public university admissions and state contracting, setting off a firestorm he said he had strained to avoid. Black legislators staged a sit-in at the governor’s executive suite. Thousands marched on the Capitol. And Mr. Bush’s inbox swelled with the pleas of students, asking why he was quashing their chance to attend college.

It was, allies say, neither the first nor the last time that Mr. Bush’s good intentions had been misunderstood on a matter of race. The most recent example arrived last week, as Mr. Bush told a crowd in South Carolina that Republicans should not appeal to African-Americans with promises of “free stuff.”

“Our message is one that is uplifting,” Mr. Bush said then, “that says you can achieve earned success.”

Opponents saw in the Sept. 24 comments a brazen hypocrisy from a son of political royalty — the latest stumble for a candidate who has cast himself as a bridge to new voters, with experience leading a diverse state and a unique perspective among Republican presidential candidates as the bilingual husband of a woman born in Mexico.

Longtime supporters heard something else: an echo of one of the most turbulent episodes of his governorship.

Mr. Bush had not planned on a fight upon entering office, at least not on this count. Chastened by a narrow election loss in 1994 — he campaigned for governor as a tough-on-crime conservative who glibly predicted he would do “probably nothing” for blacks if elected — Mr. Bush had since moved to expand his outreach to new constituencies.

He co-founded a charter school serving predominantly black residents in Miami, pressed for diversity in appointments of agency heads and judges, and expressed remorse in a 1998 debate when asked about his relationship with black voters.

“Republicans have ignored the black vote in this state, and I was part of that, and it was a mistake,” he said.

As Mr. Bush took office, though, Mr. Connerly, who had helped spur a national movement to challenge affirmative action policies on state ballots, eyed Florida as his next battleground.

Mr. Bush largely agreed with him, arguing against racial quotas. But he cast the prospect of a ballot measure as needlessly divisive. Some critics saw another motivation: The vote would have come in November 2000, and threatened to increase African-American turnout for an election in which his brother was on the ballot for president. Those close to Mr. Bush have disputed any connection.

Mr. Bush proposed a third way, calling the initiative “One Florida.” It banned racial preferences at universities and in state procurements, but required state campuses to guarantee a spot for all students who finished in the top 20 percent of their class. His brother George W. Bush, then the Texas governor, had endorsed a similar approach, backing a 1996 court decision that banned racial preferences at the University of Texas School of Law but called for an “affirmative access” approach that assured admission for top graduates from Texas high schools.

In Tallahassee, Mr. Bush argued the changes would actually increase enrollment figures for minority groups — a claim that, more than a decade later, remains contested. He also said he was ordering agencies to revamp procurement protocols to encourage greater diversity among vendors.

Few groups were pleased. Some black elected officials suggested Mr. Bush had not consulted them sufficiently. Conservatives had long questioned why he refused to back Mr. Connerly’s efforts in the first place.

“I am not wobbly,” Mr. Bush responded in a March 1999 email to one skeptic. “I oppose quotas and set-asides, and can assure you that they will not be used in state government.”

By Mr. Bush’s count, he received about 20 messages a day on the subject — and answered most of them himself, suggesting the state’s Citizen Services unit lacked “the political or social sensitivities” to respond adequately.

“Kind of scary and I am very tired,” he wrote to aides at the end of his first month as governor, describing the email volume.

At times, Mr. Bush seemed wounded. “Who told you that?” he wrote back to a 13-year-old who suggested his hopes of attending college would be dashed. “Why don’t you get the person who told you an untruth to write me?”

The debate consumed much of his first year in office, cresting perhaps in January 2000, two months after Mr. Bush had issued an executive order outlining his vision.

Two prominent black lawmakers arrived in Mr. Bush’s executive suite for a meeting with the lieutenant governor. Mr. Bush, who had resisted meeting the men himself, dropped in briefly to lament the futility of their push.

“If you think I’m going to change my mind, you might as well get some blankets,” he told the lawmakers, according to one of them, Anthony C. Hill, then a state representative.

“So we did that,” Mr. Hill recalled.

© Wilfredo Lee/Associated Press A demonstration at the State Capitol in Tallahassee in March 2000 over Gov. Jeb Bush's One Florida initiative. It banned racial preferences at universities and in state procurements, but required campuses to guarantee a spot for all students who finished in the top 20 percent of their class.

Soon, the governor’s office was overtaken by the spectacle. Protesters descended on the Capitol to support Mr. Hill and his State Senate colleague, Kendrick Meek, who did not budge for more than 24 hours. Reporters raced to the premises. And in a hot-mike moment that attracted national headlines, Mr. Bush ordered aides to “kick their asses out,” unaware that his words were being recorded. His team later insisted he was talking about the reporters.

Eventually, Mr. Bush relented, slightly. He agreed to meet the lawmakers and scheduled a series of public meetings on the changes to come.

But emotions simmered still. The Rev. R.B. Holmes Jr., who was Mr. Bush’s most outspoken black supporter, said at the time that he felt double-crossed: “Instead of One Florida, it’s divisive Florida.” (The enmity did not last; Mr. Holmes introduced Mr. Bush at his presidential campaign kickoff in June and has continued campaigning for him.)

Al Cardenas, Mr. Bush’s longtime adviser and friend, said Mr. Bush feared violent demonstrations and urged his team to avoid inflaming tensions.

“It’s the only time I remember him calling me two or three times saying, ‘Don’t be too provocative,’” said Mr. Cardenas, who had advocated challenging the affirmative action supporters to a public debate.

Less than two months after the sit-in, as Mr. Bush defended One Florida in his State of the State address, an enormous protest, led by the Rev. Jesse L. Jackson, rolled through Tallahassee.

Inside the House chambers, Mr. Bush vowed that his plan would work. “This year,” he pledged, “more minority students will be admitted to our university system than last year.”

That fall, Mr. Bush and his team highlighted gains in minority admissions at state universities. But many in higher education were skeptical of the program, noting that those acceptance decisions had taken place before One Florida’s implementation.

The next year, some statistics were less encouraging. At the University of Florida, 7.2 percent of incoming freshmen in 2001 were black, down from 11.7 percent the previous year.

“When that policy was put in place, we scrambled a little bit,” Joe Glover, the University of Florida’s provost, said in an interview.

He said the program had, for better or worse, helped compel the school to revise its admissions practices by targeting groups, like low-income applicants whose parents had not attended college, to increase diversity without violating the order.

Mr. Bush’s supporters have argued that the plan fulfilled its purpose, infusing admissions policies with conservative ideals while coaxing schools to find opportunities for underrepresented groups in other ways.

An analysis by the Orlando Sentinel in 2010 found that minority enrollment in the state’s university system had not kept pace with the number of minorities graduating high school. In 1999, the report said, more than 20 percent of the state’s high school graduates and 17.5 percent of university freshmen were black. By 2008, black students accounted for 19.5 percent of high school graduates and 14.9 percent of university freshmen.

Mr. Bush’s team has pushed back since his tenure ended, noting that more students of all races had been enrolled, with particular gains among Hispanics as the state’s demographics shifted.

And according to the Bush campaign, businesses run by blacks and Hispanics received tens of millions of dollars more in state procurements by the time he left office.

But some opponents required special attention from the governor. In 2000, a student named Tania Williams engaged Mr. Bush in a multi-email exchange, predicting a return to the era of Jim Crow and asking how long Mr. Bush would wait to assess the program’s success.

“Great question and that is what I am working on to lessen people’s fears,” Mr. Bush wrote. “You are very perceptive!”

Ms. Williams asked, with a typed smiley face, if this meant she could pester Mr. Bush about a summer internship. “I don’t know if we have summer internships, but look me up nonetheless,” he replied.

In an email this week, Ms. Williams said she had gotten the internship.

She is now a lawyer in West Palm Beach, some 75 miles from Mr. Bush’s campaign headquarters.

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