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Monday, Mar 25, 2019
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Longtime Hillsborough educator Lyle Flagg dies

BRANDON - Lyle R. Flagg, a former principal and administrator who helped desegregate schools and encouraged the advancement of minority educators in his 40 years with the Hillsborough County School District died Tuesday. He was 85.
Flagg moved to the area from Maine with his wife Vivian in 1954 to escape the snow and became principal at then Pinecrest High School -- a “strawberry school” out in the rural area south of Plant City, where students attended from April until December, so they could pick strawberries during the season.
He would later become principal at Dowdell Junior High, founding principal of the modern-day Brandon High and principal at East Bay High before being named director of secondary education for the school district. He ended his career in 1990 at Armwood High, where he was founding principal and where the football field is named in his honor.
Flagg came to Hillsborough County during segregation
and into eastern Hillsborough County, where the Ku Klux Klan was ever-present, said longtime family friend Mark Nash. He helped Hillsborough County execute its desegregation plan when federal courts forced Florida public schools to desegregate in the early 1970s, Nash said.
“Mr. Flagg, to this day, is still highly thought of by those students and faculty who he led and served with,” Nash said.
School Board Member Doretha Edgecomb remembers what an inspiring person Flagg could be.
“I got to the district office because Mr. Flagg was familiar with some of my work as a tutorial teacher at Tampa Bay Tech. I was one of the few African Americans at the district office in the mid-1970s. He was open to diversity and encouraged not just black administrators, but any teacher who wanted to become an administrator,” Edgecomb said.
Flagg kept in touch with Edgecomb, even after she left the district to run for the school board and even after he retired, occasionally calling or sending a note of encouragement.
“He was an educator's educator,” Edgecomb said.
The need to help others came from his own upbringing in a family that struggled for everything, his daughter, Lee Flagg Hinkle said.
“When he and my mother married, he struggled to get through college,” Hinkle said. “He knew a lot about hardship and knew a lot of people, particularly minorities, knew what that struggle was like.
“Dad was always positive and he always encouraged us to do well, as well as doing good,” Hinkle said. “He just had the kind of demeanor that we could talk to him or look at him and know we were seeing the right example and we would do well by following his works and his actions.”
Flagg's son, Tom, has spent 31 years at the school district and has heard many talk about his father, he said, “and 99 percent of it was positive.”
His children also recall the funny stories about their dad and his stingy reputation.
“He was incensed that we would call him cheap,” Hinkle said. “He preferred to be called frugal,” she said, with a chuckle.
“He was endearingly cheap, because he grew up during the Great Depression and hard times and never spent a dime he didn't have to,” she said. “When he left Brandon High School in 1974 – he built that school and hired all the faculty – the students and boosters got together and bought him a 1974 Plymouth Duster.”
He drove it all through his years as an administrator and even after returning to school as principal of Armwood, she said.
“He drove that car into the ground. It even had holes in the floorboards. Then, when he retired from Armwood, it was a big joke, because he would say he was going to be buried in that car. The Armwood students and faculty bought him a 1990 Plymouth Sunbird,” Hinkle said.
Flagg had left the district office to open Armwood, so he could return to a school environment, she said.
“He missed being around the teachers and students,” Hinkle said.
A visitation for Flagg will be held from 6 to 8 p.m. Friday at Southern Funeral Care in Riverview. A funeral mass will be held at 9 a.m. Saturday at Nativity Catholic Church in Brandon. Former Hillsborough County Schools Superintendent Earl Lennard will preside. In lieu of flowers, the family requests contributions be made to the Lyle Flagg Endowment, University of South Florida Foundation, 4202 E. Fowler Ave., ALC 100, Tampa, FL 33620. The endowment will be used for students in educational administration.

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