Mayor Wu aims to strike a balance of insider experience, outsider perspective with new police and schools leaders

Boston’s new superintendent and police commissioner have been leaders here and elsewhere

Mayor Michelle Wu stands with Michael Cox, Boston's incoming police commissioner.David L. Ryan/Globe Staff

She launched national searches for leaders capable of transformative change. In the end, she decided the best candidates to achieve that were a Roxbury native and a neighbor just across the Charles River.

In the past three weeks, Boston Mayor Michelle Wu has announced leaders for two of the city’s largest — and most troubled — departments: the police and the public schools. With these key choices, she is near the end of the fast-paced hiring spree that has been the first eight months of her tenure, and has in place most of the team charged with carrying out her progressive agenda.

Now comes the hard part.

Incoming police commissioner Michael Cox and schools superintendent Mary Skipper each face the daunting challenge of leading an enormous, beleaguered bureaucracy, each with high ambitions, troubled history, and chronic shortcomings Wu has pledged to improve. Violent crime has declined sharply in Boston, yet the department has been racked with scandals, from overtime fraud to criminal allegations against top department and union officials. The school system also has its bright spots, but a long way to go; it recently averted a state takeover and must overhaul its special education program, English learners instruction, and transportation system.

In Cox and Skipper, Wu chose leaders who bring intimate knowledge of the work to be done from decades in Boston but also have executive leadership experience elsewhere. Cox worked in the Boston Police Department for 30 years before becoming police chief in Ann Arbor, Mich., in 2019; Skipper spent nearly two decades in Boston Public Schools, including as a principal and district administrator, before leaving in 2015 to become superintendent in Somerville.

The two major appointments, a striking opportunity for a mayor to reshape city leadership early in her tenure, lend insight into Wu’s strategy for carrying out reforms in a city often wary of change. She is seeking the best of both worlds: outsiders with the perspective to see what needs to change, and insiders with the knowledge to effect it.

“It’s important for the rank and file … to have respect for the person, and really believe they understand their lived reality,” said state Senator Lydia Edwards, a Wu ally who represents East Boston. “At the same time, sometimes you can get tunnel vision in that experience,” and leadership outside Boston means they “have lessons from other places as well.”

Cox, Skipper, and Paul F. Burke, who was named fire commissioner in June after 32 years at the department, together will lead the city’s biggest departments, responsible for the majority of the city’s budget and roughly three-quarters of its workforce.

They join a nearly complete cabinet featuring a mix of local experience and outside voices — from Sheila Dillon, the housing chief with more than a decade of experience in such a role, to Tiffany Chu, Wu’s chief of staff, who previously led a tech company. Arthur Jemison, Wu’s new chief of planning, had experience working for the city of Boston, but also in Massachusetts state government, in Detroit, and at the US Department of Housing and Urban Development.

For Cox and Skipper, firsthand knowledge of their departments is a crucial advantage in a city where relationships are paramount and outsiders are often viewed with skepticism. But that experience comes with a potential downside: They’re trying to reform systems they have already helped lead, forming alliances and biases in the process. That raises doubts about whether systemic change can truly come from within — and if it can, why it hasn’t already.

Hiring an insider to lead an overhaul “is a risk,” acknowledged Paul Reville, a former Massachusetts education secretary, but outsiders can also run into early roadblocks.

“The automatic default is, ‘Well, we need to get someone dramatic and different and transformational coming from the outside.’ But a system like Boston can be very in-grown and parochial and grind down an outsider, as we’ve seen a little bit in the last two superintendencies,” Reville said.

Experience both inside and outside Boston made Skipper a great choice, he said: “I think she’s the right person at the right time.”

Cox, too, has a close familiarity with the Boston department he will lead — including intimate knowledge of its most hideous failings. In 1995, while he was working undercover in the department’s gang unit, fellow officers mistook him for a murder suspect and beat him unconscious. The department tried to cover up the incident for years, with nearly two dozen officers denying they had even witnessed the attack.

“I have dedicated my life to making sure that both the Boston Police Department and policing in general has grown and learned from the experiences that I went through,” Cox said at a news conference last week.

But much of the department’s hidebound, accountability-resistant culture persisted during the years Cox spent in leadership. He served in a number of prominent posts, including as a leader in the department’s internal affairs division, which handles complaints made against officers. Globe reviews have found that the department rarely doles out meaningful punishment to officers found to have acted inappropriately and has even engaged in coverups of officer misconduct.

Cox is a “strong candidate,” said Jamarhl Crawford, a longtime activist who served on the city’s police reform task force. But, he added, “I am not as convinced that he is a strong change agent. I’m not doubting that he is. I’m just saying that I have not seen any evidence of that.”

Others expressed optimism about Cox’s potential, noting that he had limited power in the department when he worked under previous commissioners. His familiarity with Boston’s force will be a significant advantage, observers said, arguing that real change can occur only when a leader is trusted by his team.

Cox offers “the best of both worlds,” said Tom Nolan, an Emmanuel College professor and former Boston police lieutenant who served with Cox decades ago.

“In any department, but especially a department like Boston that’s so firmly entrenched in the old ways of doing things … you need to have a leadership team that’s behind you,” he said. “Someone coming from the outside is going to be challenged to identify who to select.”

Cox starts as commissioner Aug. 15, and Skipper will take over as superintendent in late September. For now, residents will have to wait to see whether Wu’s choices can achieve the changes she has promised.

“[Cox] is the person that we all have faith and hope in, given his background and given his experience and commitment to making things happen for people in a different kind of way. But we all understand that sometimes good intentions meet resistance that can’t be overcome,” said Geraldine Hines, a former justice on the Massachusetts Supreme Judicial Court who led the police commissioner search committee. “He’s going to need support from the community and from the mayor and from the department to get things done. So let’s just hope that he gets what he needs.”