Cortines recalled that Giuliani called him one evening and said he needed an urgent meeting. When Cortines arrived at Gracie Mansion, the mayoral residence, Giuliani kept him waiting all night.
"I should have just left," Cortines said. By October 1995 he quit.
"It was becoming the Ray and Rudy show," Cortines recalled. "I didn't come there to fight with the mayor. But I wasn't going to be a milquetoast and let him steamroll me."
The next school chancellor, Rudy Crew, was backed by Giuliani. When he arrived, Crew told Cortines his problem was he didn't know how to handle Giuliani. "I told him, 'you'll see,' " Cortines recalled.
At first, the relationship blossomed. Crew and Giuliani took in games at Yankee Stadium. Another time, a news photo captured them smoking cigars.
Crew soon was being praised for demanding accountability, and test scores began to rise.
"The schools were really thriving under Rudy Crew," said Robert Tobias, former chief of student testing in the school system. "He was a visionary."
But, after a few years, Crew ran into trouble with Giuliani. Some analysts attribute those problems to a conservative shift in Giuliani that accompanied his aborted 1999 campaign for the U.S. Senate.
By then, Giuliani had embraced school vouchers, and he supported shifting millions of tax dollars to a pilot program for parents choosing private schools.
Crew strongly opposed vouchers, which he calls "an idea that at its heart is about breaking the back of public education," and he recalled that Giuliani never discussed his voucher plan with him. In fact, he learned about it from reporters, which he says gave him a new understanding of "what he [Giuliani] was capable of doing unilaterally."
In April 1999, Giuliani said the school system was "dysfunctional and "should be blown up." He described the system and the officials in it "as no good and beyond redemption."
Crew responded the next day with in an open letter to the media, calling Giuliani's comments "destructive" and "reckless."
"When the mayor declares that the whole school system should be blown up, he tells 1.1 million children and thousands of parents, teachers and administrators that they are wasting their time."
The Board of Education, led by Giuliani's appointees, threw out Crew in late 1999. One issue that worked against him was an internal investigation that found some teachers and principals had altered test scores.
