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Emmanuel Caulk still keeps a tattered copy of a 6th grade report card tucked away in his wallet.
More important than the grades was the handwritten note from his teacher. That teacher looked past the C鈥檚 and the fact that Caulk fell short of his goal of earning a spot on the honor roll, and instead seized on his desire to be better.

鈥淗e told me basically, 鈥業鈥檓 not going to lower the bar for you. I understand where you鈥檙e going, and you鈥檙e going to get there. If you keep applying yourself, keep making those great choices, you鈥檙e going to get there,鈥� 鈥� said Caulk, the superintendent of the .

From his work as a special education teacher in a juvenile-detention center to leading two school districts facing financial crises, Caulk has taken a similar approach in his 20-year career in education: Where others see problems, Caulk says he sees promise.

Residents, parents, and school board members say Caulk has restored calm and instilled confidence in Fayette County, a district where success had been undermined by school board infighting, a clear lack of focus on struggling schools, and constant changes in leadership.

鈥淲e had a lot of chaos,鈥� said Raymond Daniels, the school board vice chairman.

In the year before Caulk took the job in Fayette County, a 42,000-student school system that includes the city of Lexington, a state audit uncovered 鈥渃hronic mismanagement鈥� of the district鈥檚 budget and finances. Months later, the outgoing state education commissioner slammed the school system for failing to support its low-income and nonwhite students and those with disabilities. And the district had just wrapped up a contentious redistricting process that changed the home school assignments for more than 5,000 students and left many families feeling overlooked.

Within months of landing in Lexington, Caulk rolled out a 100-point district-turnaround plan that focuses on the minute and major, but is centered on engagement鈥攚ith families, with data, and with reality.

鈥淎 lot of people say, 鈥極ne hundred things?,鈥欌�娾�� said Daryl Love, a school board member for the past seven years. 鈥淲ell, these are things we need to get right. It was trying to understand where we are and then where we need to go.鈥�

As Caulk pushed to change the district, the move to Lexington brought life-altering change on a personal level.

During those first few months on the job, doctors discovered a malignant tumor in Caulk鈥檚 sinus cavity. After enduring an 18-hour surgery in the fall of 2015, he went through a months-long recovery.

鈥淭he community lifted me up,鈥� Caulk said.

Now, in his third year, Caulk is focused on trying to return the favor: he is reshaping a district in the midst of unprecedented demographic and economic change: The number of English-language learners and students who qualify for free and reduced-price meals has swelled in recent years.

To address the state鈥檚 concerns about management, Caulk has engineered an administrative-staff shakeup, one designed to free up principals to spend more time coaching and supporting teachers and less on day-to-day tasks.

As part of that plan, he鈥檚 stressed that schools should know why students struggle and succeed, using data as a guide. To that end, the district has also managed to hire more teachers to work with special education and gifted and talented students.

鈥淗e has done yeoman鈥檚 work in righting this ship and galvanizing the system,鈥� said Porter G. Peoples, the CEO of the Urban League of Lexington-Fayette County. 鈥淲e were in a state of decline.鈥�

While things are looking up, Caulk estimates that the district is at least five years away from reaching its goals despite the changes he鈥檚 instituted. It鈥檚 a challenge he鈥檚 embraced, school and community leaders say.

鈥淢anny, as you can tell based on his history, his r茅sum茅, has never been afraid to take on a challenge,鈥� said Alan Stein, a prominent Lexington businessman and civic leader. 鈥淲hile there was some acrimony, and some disarray [in the district], a good leader can look into that and say, 鈥榃ow, if we can fix that, the sky is the limit.鈥欌��

鈥楢 Piece of the Puzzle鈥�

Caulk, 46, has moved frequently in his career, working as a teacher and principal in charter and traditional public schools in his home state of Delaware and in rural Pennsylvania, and serving as an administrator in Baton Rouge, La.; Chicago; and Philadelphia before taking his first superintendent鈥檚 job in the 7,000-student Portland, Maine, public schools.

Along the way, he even took a hiatus from education in the early 2000s to work as an assistant prosecutor and education law attorney in New Jersey.

When the Portland school board hired Caulk as its superintendent in 2012, the district was just emerging from a disastrous financial scandal that forced out the previous schools chief.

鈥淚鈥檝e always wanted to put myself in uncomfortable positions and situations ...to learn about myself and to learn about others,鈥� Caulk said. 鈥淚t鈥檚 a challenge, and I feel like I can make a difference. That I can be a catalyst. Not the difference, but a piece of the puzzle.鈥�

The school board wanted a leader who would foster community ties.

They chose Caulk, who was working as an assistant superintendent in Philadelphia at the time, overseeing 36 schools that educated 16,000 students. During his time in Portland, Caulk helped the district establish a multiyear budgeting process, devise a comprehensive master plan, and create the Portland Education Foundation to raise private funding for schools.

鈥淗e weathered the storm of what was going on here,鈥� said Ed Bryan, a former Portland school board member and the current vice president of the district鈥檚 foundation. 鈥淗e did a pretty good job of steadying the ship and getting us back to a place where we could move forward.鈥�

And then, he was gone after three years, off in search of his next challenge.

鈥淎 bigger and better opportunity came up that fit with his vision,鈥� Bryan said. 鈥淪ome superintendents are wonkish about education and some superintendents have more of a 50,000-foot view and want to do more, be more community-facing. Manny was somebody that could really do both.鈥�

Those skills have come to the fore in Lexington, a place Caulk calls the 鈥渨ealthiest, most [needy] district鈥� he鈥檚 worked in. For every pocket of prosperity, there鈥檚 another of poverty. For the first time in district history, more than half its students qualify for free or reduced-price meals.

Magnet programs in the district are thriving, but hiring teachers for its growing English-learner population has proved challenging.

A state review conducted last May determined that while the district now has the capacity to shore up academics in its poorest-performing schools, the work remains incomplete. Due to a decline in test scores during Caulk鈥檚 first year, the district鈥檚 overall rating dropped from 鈥減roficient鈥� back to 鈥渘eeds improvement,鈥� where it had stood two years prior.

In response, Caulk instituted so-called 鈥渆mpowerment zones鈥� that provide a school-based instruction specialist, support team, principal-leadership coach, and extended school days for students in the schools that are struggling the most.

While he鈥檚 shoring up his neediest schools, his school board has also pressed him to marshal more support from those outside the district. That sparked a partnership with the philanthropic arm of the Ford Motor Co. that will allow thousands of students in three district high schools, known as the Academies of Lexington, to focus their studies on potential careers such as engineering or health care.

Through community book club discussions and parent-advocacy classes, Caulk has also emphasized outreach to families, including those from groups who are often reluctant to participate in schools, said Kathleen 鈥淧enny鈥� Christian, the first vice president of the Fayette County schools parent-teacher association. He wants two-way communication, including critiques and criticism, she said.

鈥淚鈥檝e seen my share of false promises,鈥� said Christian, the mother of a middle school student and three district graduates. 鈥淗e wants us to say, 鈥楳anny, this does not work for us.鈥欌�呪��

Rapport and Relationships

While ratcheting up standards and expectations, Caulk has also managed to build a rapport with wary employees.

鈥淗e does that without making people feel like their best isn鈥檛 good enough,鈥� said Jessica Hiler, the president of the Fayette County Education Association, the district鈥檚 teachers鈥� union. 鈥淭hat鈥檚 his mission. I think everybody鈥檚 taken that on.鈥�

Caulk said he can relate to all district employees and how tough the work can be, not only for those who teach in classrooms but also for those who clean them and feed and transport students.

In his first school-related job, Caulk worked as a contract custodian in the Brandywine, Del., district the summer after high school graduation, cleaning classrooms in preparation for the start of school.

鈥淭hat didn鈥檛 go well,鈥� he said. 鈥淚 showed up on time, got along with my co-workers, you know all those soft skills we talk about. But I couldn鈥檛 get the job done.鈥�

There was no apprenticeship program, or even a how-to guide, to help him work the buffer as he waxed classroom and hallways floors.

Caulk鈥檚 supervisor had a blunt message for him: Go to college and be a teacher. You can鈥檛 cut it here.

Said Caulk: 鈥淚 thanked him for that career advice.鈥�