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.