Jacob Oliva, Still a Flagler Resident, Is One of Three Finalists for Miami-Dade Superintendent

Oliva, the son of a Cuban father, is a native of Miami-Dade. He was in Flagler County schools for 17 years as a teacher, principal and district administrator. The Flagler school board appointed him superintendent in 2014, replacing Janet Valentine. He’d served as Valentine’s deputy until health difficulties forced Valentine into retirement. Oliva was a popular, visible and charismatic superintendent, so his elevation to the Department of Education as vice-chancellor in January 2017 was only initially surprising.

Oliva, 47, is still very much a Flagler County resident: He is homesteaded in Palm Coast, where he and his wife own a home, he is registered to vote in Flagler (as a Republican), his daughter attends Flagler Palm Coast High School, and his brother is a teacher at Matanzas High School.

Oliva’s decision to keep his base in Flagler is not unusual with government employees who serve political appointments that can be unpredictable, though in this case it is Oliva who is indicating his intentions to move on from Tallahassee–perhaps surprisingly, considering the high-profile position he holds, perhaps not so surprisingly, considering the increasingly reactionary nature of the administration he serves.

As chancellor, Oliva has been the public face of Gov. Ron DeSantis’s doctrinaire opposition to mask mandates in public schools, testifying in court on behalf of the administration’s stance when Miami-Dade was among the districts challenging the prohibition. But that is not the only reason why Oliva’s candidacy may be a long shot in Miami Dade.




The Miami Herald calls candidate Jose Dotres “favored” for the job, because of Dotres’s long tenure with Miami-Dade schools. He is currently the deputy superintendent of Collier County schools after 30 years in Miami-Dade, where he’d been chief of staff, director of human resources and area superintendent, and who, according to the Herald, has “developed relationships with key School Board members, including Chairperson Perla Tabares Hantman, who has been on the board 25 years.” He has also developed trusted relationships with union leaders.

The third candidate is Rafaela Espinal, a native of the Dominican Republic who grew up in new York City and developed a career in city schools. She is currently an assistant superintendent for innovation (a title Oliva could have held informally when he was Flagler’s superintendent).

Last week a Miami-Dade school board member nominated Dotres to be superintendent even as the board was narrowing its shortlist, but other board members preferred continuing with the process in play. That process has come under sharp public criticism for being hurried and less than deliberate. The board is seeking to replace Alberto Carvalho, who resigned after 14 years as superintendent to take over the Los Angeles Unified School District, the nation’s second-largest (after New York City; Chicago is third).

The school board opened only a seven-day window for applications, an astoundingly brief period that drew just 16 candidates, and that seemed as if designed as window dressing around Dotres’s candidacy: the board’s job description, emphasizing deep ties to the Miami-Dade community and its district, was as if written with Dotres in mind.

In essence, Oliva is finding himself a candidate in a process that has uncanny similarities with his own candidacy for superintendent in Flagler in 2014, when he was the candidate the Flagler school board had in mind all along as it bypassed a broad search and hurriedly moved toward a hire. He was one of three finalists then, too, and had his own ringer on the advisory committee tasked with recommending finalists. A unanimous board unsurprisingly appointed him superintendent. Now, despite his broader and deeper experience, he may be outflanked in Miami-Dade by Dotres’s Olivaesque inside track.




The Herald in its profiles of the three candidates referred to Oliva’s humbler beginnings, his tenure in Flagler, his assurance that he would not alter Miami-Dade’s strict Covid rules. It also reports on a December 2021 Office of Inspector General investigation of his and two other officials’ alleged involvement in a controversial bidding process focused on Jefferson County schools. The two other officials–former State School Board member Andy Tuck and Executive Vice Chancellor Melissa Ramsey have resigned. Oliva told the Herald he was no longer associated with the company that listed Tuck and Ramsey as principals, and that the investigation cleared him.

The Herald–which incorrectly refers to Flagler schools as having 2,500 teachers: it has 1,700 employees in total–quotes Flagler School Board Chairman “Trent” Tucker (it is actually Trevor) lavishly praising Oliva’s years in the district and his implementation of classroom-to-careers programs, the digital initiative that put a tablet or a computer in every student’s hands (and helped Flagler pivot to remote learning without missing a beat in 2020), and his strength as a consensus-builder.

The Miami-Dade school board conducts open interviews of the three candidates starting at 2 p.m. Monday. The district’s web page states that “The public may view or read the Closed Captioning of the Special School Board Meeting which can be found by accessing https://www3.dadeschools.net/SchoolBoard/information and clicking on the Web Simulcast button in the Navigation on the left side of the page.”