“It’s a culmination of 42 wonderful years in public education, all in the state of Florida,” said Grego, who emailed friends and supporters with the news early in the day. “I’ve loved every minute of it.”
Grego has led the Pinellas district for the past 10 years. Before joining the district, he worked as superintendent of Osceola County schools, state chancellor of K-12 schools and assistant superintendent of Hillsborough County schools, where he spent 28 years, mostly as an administrator.
He said the timing is right for him to go. He’ll turn 65 in the spring, and he feels good about the district’s situation and direction.
“It’s time to pass the baton off,” Grego said in an interview, adding he plans to remain in the community after retirement. “I see only bright things for Pinellas.”
Superintendent turnover in Florida has been high lately among Florida’s largest districts.
Broward and Miami-Dade counties have superintendent searches ongoing, as does Lee County, which this week announced five finalists for its top job. The Palm Beach and Polk school districts hired new superintendents within the past year.
School Board chairperson Eileen Long praised Grego — Florida’s 2018 superintendent of the year — for bringing stability and success to the district. She cited his efforts to help increase graduation rates and upgrade school buildings among other improvements.
“Dr. Grego has put us in such a wonderful spot,” said Long, a retired teacher who didn’t always hold the superintendent in such high regard. “Now we’re looking forward.”
Long recalled the “roller coaster” Pinellas schools endured after the 2004 departure of Howard Hinesley, who led the district for 14 years. She said she did not want a repeat of that situation.
Hinesley’s successor, Clayton Wilcox, lasted four years in the job, followed by Julie Janssen, a longtime Pinellas educator whose tumultuous tenure ended after three years. An interim leader, John A. Stewart, preceded the arrival of Grego, who became the district’s fifth superintendent in a span of eight years. At one point before Janssen took over, the School Board voted to hire Miami-Dade educator Alberto Carvalho, who came for interviews but ended up jilting Pinellas and taking the superintendent’s job in his home county.
Grego got the district back on track, said Pinellas County Commissioner Rene Flowers, who served two terms on the School Board.
“The things he wanted to accomplish, he did that amidst all the criticism,” Flowers said. “He took a lot of arrows, he took a lot of bricks, a lot of blows. And it took a lot prayer to keep him lifted up. … I think he did a wonderful job coming here when he did, with all the turmoil that was going on.”
The board will work with the state’s school boards and superintendents associations to look for the best possible next chief executive, Long said.
“Some people in our system would make wonderful superintendents,” she said, suggesting candidates should understand Florida education. But “I don’t know where the next one will come from. We’re going to look inside and outside.”
Grego laid a solid foundation for his successor, in part by developing a good group of top leaders working in his administration, said School Board member Laura Hine.
“I know the right leader’s going to come,” she said, referring to the next superintendent. “I think he’s created stability and an environment for us to thrive. And you know sometimes it’s good to get a new leader, so it’s an exciting time.”
Pinellas’ next leader will have big shoes to fill, said Florida School Boards Association executive director Andrea Messina, who will likely help the board with its search.
“He has always been a steady, calm, reasoned voice and leader,” Messina said of Grego. “Everyone has looked to him across the state for consistent leadership.”
In late 2020, Grego led local superintendents in pushing back against a decision by the University of South Florida to phase out undergraduate programs in its College of Education. Grego and his colleagues, noting that USF is a training ground for thousands of area teachers, called the proposal a “terrible mistake” and the university reversed itself.
Pasco County superintendent Kurt Browning called Grego the dean of Florida superintendents, and said his ability to come to the table with solutions and ideas helped school districts around the state.
“That’s tough to do in this environment,” Browning said, noting how it has become more difficult in recent years to manage school districts in the face of rising contentiousness within communities.
Grego said the challenges of the past two years did not prompt his decision. Tough times come and go, he said, noting his career had spanned major recessions and housing booms, the 9/11 terror attacks and the 2018 Parkland school shooting.
“It’s part of the job,” Grego said. “There’s going to be another challenge two or three years down the road. Life doesn’t really stop.”
Education commissioner Richard Corcoran said Grego’s retirement would be a “tremendous loss” for Pinellas and the entire state. Grego represented the state superintendents association in many dealings with the state as everyone worked through coronavirus pandemic protocols, among other issues.
“Mike has been one of my greatest advisers,” Corcoran said. “I thank him for all he’s done and wish him all the best.”
During his tenure, Grego developed a plan to reduce the academic achievement gap among races within the schools. Some of the district’s lowest performing schools, which had among the poorest test scores in the state, made dramatic improvements through the initiatives.
Though the results have showed steady progress, more work remains, said Ric Davis, a leader of Concerned Organization for Quality Education of Black Students.
For instance, the district has seen the graduation rate of Black high school students rise from 69 percent in 2017 to 86 percent in 2020. That group continues to have the district’s lowest graduation rate, though.
“The issues that we’re concerned about are still with us, so we have to continue to work with them,” Davis said. “We have to wait and see when the new superintendent comes in what thoughts and ideas they bring.”
The district also has some mending of fences to do with its teachers union, whose leaders recently accused the administration of bargaining in bad faith over items such as longevity supplements. Some teachers have complained about working conditions worsening during the pandemic.
“We have not always seen eye to eye on issues surrounding the teachers,” Pinellas Classroom Teachers Association president Nancy Velardi said, referring to Grego. “We wish him a happy and relaxing retirement.”
Grego’s record also includes a move to have gifted education programs in all elementary schools. He promoted career education and early learning programs, and pushed to make improvements to many of the district’s aging school buildings with a $750 million modernization program.