Mayor-elect Bill de Blasio aside his pick for first deputy mayor, Anthony Shorris. Next to Shorris are Dominic Williams, who will be the first deputy mayor's chief of staff, and Emma Wolfe, de Blasio's director of intergovernmental affairs.
Mayor-elect Bill de Blasio aside his pick for first deputy mayor, Anthony Shorris. Next to Shorris are Dominic Williams, who will be the first deputy mayor’s chief of staff, and Emma Wolfe, de Blasio’s director of intergovernmental affairs.

As the dust settles from Mayor-elect Bill de Blasio’s two-day spree of administrative appointments, all eyes have now turned to his next big decision: who he’ll pick for New York City schools chancellor.

Speculation around a handful of candidates has been around for months, but this week the rumored list was shuffled and whittled down. Some names have vanished while others surfaced at the top of the rumor mill, a rearrangement that reflects concerns that de Blasio’s top administrative picks so far aren’t diverse, observers say.

The newest contenders to emerge are Kaya Henderson, District of Columbia’s schools chancellor, and Chicago schools chief Barbara Byrd-Bennett, who was in New York City recently, fueling rumors of her candidacy, sources said. Montgomery County Superintendent Josh Starr also remained in the mix, as did New York-based Carmen Farina, the city’s former city chief academic officer and Regent Kathy Cashin.

Andres Alonso, the former chief executive officer the Baltimore schools once considered a frontrunner for the job, has not been mentioned as prominently.

The short list of education leaders outside New York City reflects a wide swath of backgrounds and ideas about education policy, some of which seem to align closely with de Blasio’s views, and some of which don’t. For de Blasio and his advisors, their choice will be a signal of how faithful he plans to stick to some of the campaign pledges that helped distinguish him from more centrist Democratic candidates during the primary.

De Blasio himself has said nothing publicly about who he’s considering for the job, other than acknowledging this week that he’s begun talking to candidates. A de Blasio spokeswoman also declined to comment or confirm details about the selection process, which is taking place mainly behind closed doors.

Starr, Henderson and Byrd-Bennett share at least one thing in common on education. All were teachers in the New York City school system before moving up their career ladder. They also all run relatively large school districts, though they range in size (Chicago has 400,000 students compared to Montgomery’s 150,000 and D.C.’s 45,000) and demographics (Montgomery County, which runs up to the edge of D.C. boundaries, is largely suburban).

Their differences in other areas are stark, which could factor into de Blasio’s decision. Of the three, Starr, 44, appears to have the most in common ideologically with the mayor-elect. Both de Blasio and Starr are opposed to using tests scores as an accountability tool to measure the performance of teachers and schools, and both have railed against the use of school grading systems like the one New York City currently has.

Both are also against using test scores as a sole determinant in student admissions policies, a position that moved Starr  to try to desegregate middle school classrooms during a six-year superintendency in Stamford, Conn.

Starr was in Brooklyn last week and it is reported that de Blasio’s team has reached out to him. A spokesman for Starr did not comment on the reports, saying only that he is “aware that his name has been mentioned for the position.”

But observers say chances may have faded a bit for Starr, who is white, after seeing who de Blasio picked this week for first deputy mayor, Anthony Shorris and police commissioner, Bill Bratton.

“Given his commitment to wanting a diverse government, his selection of two white males for the two key appointments he’s made, I would think, raised the probability that the appointment of the schools chancellor would will not be a white male,” said Joe Viteritti, a professor of public policy at Hunter College who has advised school leaders in New York City, San Francisco and Boston.

Henderson and Byrd-Bennett, both African American women, are seen as being on the other side of the education reform spectrum. As leaders of urban school districts that have pushed aggressive policies around teacher evaluations, charter schools and intervention for struggling schools, they are closely associated to Bloomberg’s brand of reform, which de Blasio ran against in the election.

For Byrd-Bennett, it’s not the first time her name has been floated for chancellor — this year or even this decade. She was reportedly then-Deputy Mayor Dennis Walcott’s top choice for the job when Mike Bloomberg took over City Hall in 2002.

Byrd-Bennett ran the Chancellor’s District under Chancellor Rudy Crew in the 1990s, a group of low-performing schools that received extra resources to improve. The model has been cited by Michael Mulgrew and Randi Weingarten as a preferred intervention than Bloomberg’s school closure strategy.

But that was a long time ago. Most recently, Byrd-Bennett has enraged the union in Chicago as Mayor Rahm Emanuel’s schools chief. Last year, Byrd-Bennett was the face of the administration’s cost-saving plan to shutter 49 school buildings, a story that gained national headlines.

Byrd-Bennett still has close ties to New York City, however, and some see her work in Chicago more as an extension of Mayor Rahm Emmanuel than a reflection of her actual positions.

She was in New York City prior to Thanksgiving, a source said, fueling speculation that she is being taken seriously by de Blasio. The source did not know specifics of the trip.

A Chicago Public Schools spokeswoman, said she “can’t confirm her travel schedule” when asked of Byrd-Bennett’s visit.

Henderson, under then-Chancellor Michelle Rhee, helped negotiate a 2010 teachers contract that included merit pay for high-performing teachers and helped implement the district’s new teacher evaluation system. In 2011, she took over for Rhee, who resigned when the mayor who appointed her lost a re-election.

Henderson has continued most of the district’s reforms, but without the brash managerial style that made Rhee a divisive presence both in D.C. and nationally. This year, D.C. saw big student gains on national tests, though it still ranked low in overall achievement.

A spokeswoman for Henderson confirmed she had spoken to de Blasio, but did not say what they talked about.