TIP OF THE MINCBERG: Cathy Mincberg when she was in Houston.

If former Portland Public Schools Superintendent Vicki Phillips was the district's President Bush, chief operating officer Cathy Mincberg was her Karl Rove, the brainy insider to whom Phillips turned when she needed "damage control" on her sweeping and sometimes unpopular reforms.

As politically ambitious as Phillips, Mincberg once ran for Houston City Council. But she largely stayed in Phillips' shadows for much of her boss's three-year tenure in Portland, influencing decisions, from public relations to food service and building management, behind the scenes.

Now, as the School Board prepares to select Phillips' replacement, questions swirl. Will Phillips' right-hand woman stay or go—just as Phillips did last month when she left for a higher-paying job at the Bill and Melinda Gates Foundation? And, if Mincberg stays, will she serve Phillips' successor or will she be Phillips' successor?

To a large extent, Phillips' legacy depends on how the School Board answers those questions. Hiring a superintendent who won't abandon the changes Phillips made—to school configuration patterns and textbook options, for example—would make Phillips look good.

Phillips has already vowed to stay involved in Portland, and an ally like Mincberg would help her wield greater influence from her post as Gates' education director of the Gates Foundation, where she'll oversee more than $3.4 billion, including a $2.6 million grant to PPS. (When Phillips left her previous superintendent's job in Lancaster, Pa., she had a hand in picking her successor, Ricardo Curry. He was sentenced to two years in prison after investigators revealed fraudulent spending and hiring practices.)

Several internal candidates in Portland besides Mincberg appear to be possible superintendent contenders, even though none has been a superintendent. The list includes chief of staff Carole Smith, human resources director xRichard Clarke, and chief of teaching and learning Judy Elliott.

But the specter of a Mincberg administration most worries and angers the parents who criticized Phillips' changes the loudest.

"We've seen Cathy Mincberg in action, and it was purely tactical and without a strategic vision," says parent Ben Joy, whose experience fighting the closure of Rose City Park Elementary School has prompted him to plan a run for School Board.

Mincberg, 55, who makes $140,000 a year, told WW in an email that she is considering applying for the top job. "Being the superintendent for Portland would be an honor," she wrote.

Mincberg's time in Houston as the $160,000-a-year chief business officer raises a few red flags about her suitability to run Portland's schools, a district one-quarter the size of Houston's.

Mincberg's projects there were grand. She is credited with generating $200 million in federal grants to support the purchase of new technology.

But she also generated a backlash among union leaders and parents when she supported the idea of teachers working extra as school bus drivers for $10.32 an hour.

"Why not have us come in on Saturday and do the lawn?" Coletta Sayer, president of the Houston Classroom Teachers Association, told the Houston Chronicle.

Mincberg was also among a number of administrators called out by the Chronicle in 2004 for accepting gifts from businesses with school district contracts. Although the practice was not against district policy then, Mincberg accepted Super Bowl tickets from Hewlett-Packard, the recipient of a multimillion-dollar contract with the district at the time.

Portland School Board co-chair Dan Ryan declined to discuss possible candidates.