TAMPA — For two decades, his star rose in the Hillsborough County school system as a well-regarded educator who finally got a principal's job last year at Freedom High. Then last month, he told parents, teachers and students he was stepping down for health reasons and would take another job with the district.
There is more to the story of David Sheppard — details left out of the official explanation, details that may or may not be related to his departure but that have raised questions.
A female employee he evaluated at a previous school was charged with stalking Sheppard, sending letters and emails that described a relationship between the two. The school district says it looked into an anonymous complaint alleging an affair, but said it had no records of its investigation. Meanwhile, the Hillsborough County Sheriff's Office is looking into the death of Sheppard's wife five days after he stepped down as principal.
Investigators are still working to sort it all out.
The body of Donna Sheppard, 44, was recovered from the swimming pool at the family's Lutz home on the afternoon of Oct. 29, officials say. The Hillsborough Medical Examiner is conducting toxicology and other tests to determine the cause of death.
So far there is no evidence of a crime, sheriff's spokesman Larry McKinnon said.
David Sheppard's departure announcement followed a 20-year career in which he received glowing evaluations as a science teacher and was widely respected as an administrator, becoming principal at Freedom in New Tampa in February 2012.
"In my wildest dreams, I cannot imagine anybody not liking him," said Maxine Stark, who taught math at Wharton High School, where Sheppard was assistant principal before moving to Freedom.
Sheppard dealt with difficult personnel issues at Freedom, including some that attracted media attention. But the public did not know he also was getting unwanted attention from Tracey Seenath, a secretary he had worked with at Wharton.
Seenath, a mother of two who was divorced in 2011, left the school that year, citing child care difficulties. After a leave of absence, she became a property control clerk for the district.
According to an affidavit signed by a sheriff's detective, Sheppard ended a relationship with Seenath in late 2011, and soon after she began to stalk him. In her letters and emails, she threatened to hurt him and his family, as he had hurt her.
Seenath declined to comment for this story, and Sheppard did not respond to a reporter's request for comment.
But, according to the arrest affidavit, Seenath taped letters to Sheppard's car and home mailbox that said, "I LIE and CHEAT ON MY WIFE." She wrote letters about Sheppard's alleged infidelity and sent them to family members, administrators throughout the district, and the principal of his child's school. Sheppard's mother-in-law, Nancy Barlow, got one in the mail, all the way in western Pennsylvania.
In addition to calls and texts, Sheppard received nearly 5,000 emails from Seenath's school district address. They escalated, with 200 arriving between Sept. 2 and Sept. 11, when deputies arrested Seenath on charges of aggravated stalking.
On Sept. 3, according to the affidavit, Donna Sheppard photographed Seenath putting a letter in the Sheppards' mailbox. Addressed to the School Board, it described their relationship and how it had affected her.
Board member Cindy Stuart received one such letter — which was written anonymously — on Sept. 13. She asked for an investigation. That job fell to deputy superintendent Dan Valdez.
The Tampa Bay Times requested records of the investigation, but district spokesman Stephen Hegarty said he did not know of any. Sometimes matters such as this one are handled orally without creating a file, he said. As to whether Sheppard had an inappropriate relationship with Seenath while acting as her supervisor, it's unclear if any district officials knew or even asked, before or after Sheppard was promoted.
Hegarty described the recent investigation as follows:
Valdez referred the matter to professional standards manager Linda Kipley. She kicked it back up to Valdez when she realized Sheppard had evaluated Seenath at Wharton, and Seenath had been arrested on charges of stalking him. Sheppard and Valdez spoke in person and by phone. "Mr. Valdez was well aware that Mr. Sheppard was the victim of alleged stalking, which was causing a great deal of pain to him and his family," Hegarty said.
On Oct. 22, Sheppard told Valdez he could no longer be principal. That made the question of a relationship moot, Hegarty said. "Because he would not be supervising anyone, Dan didn't seem to feel the need to pry into his personal life beyond that."
Sheppard made his announcement to the Freedom staff Oct. 24 and reported Oct. 28 to a temporary job in the district's professional standards office, Hegarty said. A permanent arrangement had not been found when his wife died the following day.
The Times spoke with several of Sheppard's colleagues at Wharton, who insisted they never suspected anything inappropriate with the staff. They described Sheppard as a talented teacher and administrator with a calm demeanor and a dry sense of humor.
He embraced technology before most other administrators, said Ann Sofia, former head of the English department. He had a knack for satisfying parents without undermining teachers. He took care to make sure students were distributed evenly among the classes, said math teacher Michael Rush. It mattered that teachers trusted him.
In situations involving student misconduct, "you knew the kids were going to be disciplined appropriately, but he was never harsh," Stark said. "He followed the rules."
Some worried when he mentioned concerns about his health. It was widely known that, as a teenager, Sheppard was the first patient at the H. Lee Moffitt Cancer Center. "People were telling me he was looking bad," said Wharton math teacher Carlos Rosaly. "I thought maybe the cancer had come back."
Concern turned to shock with Donna Sheppard's death, coming a day before her husband's 44th birthday. "I had to hang up," Sofia said. "I almost got sick. I was speechless."
A massage therapist raising two school-aged children, Mrs. Sheppard was born in Pennsylvania and grew up in the Tampa Bay area.
She and David Sheppard met as students at King High School and married in 1993.
"She had a sweet spirit about her," said Rosaly. "She was beautiful outside and beautiful inside."
She suffered from migraines and fibromyalgia, said Barlow, her mother. But she was devoted to her kids and determined never to let Seenath get the best of her.
School officials cannot say when or where Sheppard will return to work. Seenath, now on unpaid suspension from the district, has pleaded not guilty and will be arraigned Dec. 10.
Times researcher John Martin contributed to this report. Marlene Sokol can be reached at (813) 226-3356 or firstname.lastname@example.org.