The next Hillsborough superintendent: Who’s on the short list?

The names started flowing soon after Hillsborough County school superintendent Jeff Eakins announced Monday that he’d be leaving.

“Literally every conversation I have had has brought up someone else’s name,” parent activist Melissa Erickson said, declining to repeat any of them with a diplomatic, “whoever is chosen will get a lot of support.”

Among those getting repeat mentions were Pinellas superintendent Mike Grego, current deputy superintendent Chris Farkas, and former district chief of staff Alberto Vazquez.

School Board members said they’d like to see a national search for Eakins’ replacement. The eighth-largest school district in the country should be able to attract top talent, after all.

PREVIOUS COVERAGE: Hillsborough school superintendent Jeff Eakins will retire in a year

But whether an out-of-state candidate would have the political connections and statutory understanding of Florida’s education model could prove a hurdle to bringing in a hot shot with a profile. Even finding someone from inside Florida could be a tough sell, knowing they’d be coming to a district with a history of infighting, financial troubles and academic struggles.

In 2005, the board hired a Wisconsin-based search firm to root out candidates for superintendent. It brought in leaders from Louisiana and Connecticut, Michigan and Miami.

But in the end, the board picked MaryEllen Elia, then the district’s head of facilities, leaving intact its decades-long practice of hiring from within.

That’s not a terrible strategy for a district that’s so large and prominent, suggested Florida School Boards Association executive director Andrea Messina, who also runs superintendent searches.

“The School Board is going to have to decide what they are looking for,” Messina said. “But typically, as a school board member, I would want any superintendent to be developing the talent that could take over when they leave.”

Another factor at play will be Florida’s broad open records law, which makes applicant information public. In the past, some headhunters have complained that top qualified aspirants might choose not to apply because they don’t want their current bosses to know they’re casting about.

Adding to the mix, five other Florida school districts also need a new superintendent. Counties such as Volusia and Escambia are smaller than Hillsborough from a state perspective, but they’re much larger than most school districts in the nation, which could prove competitive. Volusia, for example, falls in the top 70 districts in the U.S. by enrollment.

So who might end up in the downtown Tampa superintendent’s seat?

One of the most frequently mentioned possibilities is Mike Grego, 62. In many ways, the Pinellas County superintendent of seven years is a top prospect, despite being closer to the end of his career than the beginning. He came up through the Hillsborough district, leaving in 2005 after losing the top spot to Elia. He’s a recent Florida superintendent of the year, served as state K-12 chancellor, taught at the University of Central Florida and ran the Osceola County school district, as well.

The idea of Grego leaving Pinellas crossed several of his current board members’ minds as soon as the Eakins news broke.

“You don’t think Grego,” board member Eileen Long said during an interview, a panicked look in her eyes.

“I’m sure everybody in Hillsborough would like him to come over and be superintendent. People know him, they respect him, and they’ve seen what he’s done here,” said veteran Pinellas board member Carol Cook. “Do I think he will go? No. I think he has a job to do and his sights are focused on making progress here in Pinellas. Having said that, I hope I’m right. I really, really would not like to see him leave here for anyplace.”

Grego declined to talk about the job.

“Jeff Eakins is an inspiring leader who has transformed the lives of countless students in the Tampa Bay area through his passion and commitment to public education," he said Tuesday in a statement. "It would not be respectful to superintendent Eakins to speculate on who will succeed him one year from now. I remain focused on the important work in Pinellas County, serving as superintendent.”

A handful of insiders also get positive marks. The possibilities include Chris Farkas, 46. The deputy superintendent is a rising star in Hillsborough, who first joined the district in 1999. After teaching social studies, he reached the rank of principal at Tampa Bay Technical and then Freedom high schools. From there he was promoted to area superintendent in southeast Hillsborough and chief of operations under Eakins.

The operations job, now at the deputy superintendent level, put Farkas in charge of transportation and something that gets a lot of attention — air conditioning. Currently, he is supervising $1.5 billion in improvements that are being funded by the recently approved half-cent sales tax.

Farkas did not rule himself out when questioned Tuesday. “Those are big shoes to fill,” he said of Eakins. But, he said, “to be a good leader, you must also be a good follower. And I am also ready to follow the next person who has the job.”

Another candidate from Eakins’ team could be Van Ayres, 44. Ayres, whose mom once was Sickles High principal, joined the school district in 1997 as a teacher at Blake High. As principal of Jefferson High, a school he joined in 2012, he impressed Eakins and School Board members with the care he took to help more students overcome barriers to graduation.

Under Eakins, he was quickly promoted to deputy superintendent over instructional issues. Specifically, Ayres has worked on ways to raise graduation rates, a goal the district has met with a nearly 12 percentage-point gain since 2015. Teachers have said they like Ayres because he advocates for them and understands key issues such as student discipline.

“I am not interested at this time,” Ayres said.

Harrison Peters is relatively new to the district, but in a high-profile job. He joined Hillsborough in 2016 as Chief of Schools after a career that stretched from Orlando to Charlotte, Chicago and Houston. Peters, who was recruited by assistant superintendent Tricia McManus, has direct oversight of the district’s principals.

He has demonstrated a keen interest in struggling schools and communities — and also, a willingness to look around for career advancement. He was a finalist for the superintendent in Duval County and some out-of-state positions before that.

But, when asked Tuesday if he wanted to be in the running for Hillsborough’s top job, he said, “That’s absolutely a no.”

Kim Moore, 61, also said she does not consider herself a candidate, even though she is one of many former principals who could get a look. Moore, who has a doctoral degree, ran Middleton High from 2014 until the end of 2018 and is now the district’s director of administration. Well liked and highly respected in the Hillsborough school system, she joined the district in 2000 after a career in the military.

From an online biography: “As a Company Commander and Training Officer, Kim led hundreds of soldiers and staff. She also instructed all branches of the military in preparedness for nuclear, biological and chemical warfare, including weapons of mass destruction. This experience required a level of training, coaching and drive unlike any Kim had known while growing up in small-town Chester, Pennsylvania.”

Looking to the outside, the potential candidate names come from a variety of backgrounds.

Kurt Browning, 60, is the elected superintendent of Pasco County schools. With no formal training in education, Browning might seem an unusual prospect for the job. But he has a master’s in business administration and the political savvy of being an elected official for four decades.

The outspoken president-elect of the state superintendent’s association, Browning served as secretary of state under two Florida governors, sits on a state panel that reviews student athlete complaints to the FHSAA, and regularly is called upon to testify before the Legislature. He’s more likely to seek another four-year term in Pasco, but he has attracted attention from at least one Hillsborough board member as the head of the nation’s 55th-largest district.

Alberto Vazquez was one of Eakins’ first hires, serving as chief of staff until late 2017, when he left to become deputy superintendent of the Hartford, Conn., school district. He’s not a native, but he has long ties to the Tampa Bay area, having also worked as superintendent of schools for the Diocese of St. Petersburg.

Vazquez, currently pursuing his second doctorate, is bilingual — a skill that could help him navigate the growing district with a large Hispanic population. He was attributed with helping to reverse the district’s financial woes, implementing many budget cuts after studying spending patterns and staffing needs. He did face some controversy, though, over a whistleblower lawsuit by the district’s human resources director, who no longer holds that position.

Florida also has some up-and-coming district leaders, many with Hillsborough ties, who could emerge in a search.

Scott Howat, chief communications officer in the Orange County School District, has held positions of increasing influence in superintendent Barbara Jenkins’ top staff. He also has worked as the district’s lobbyist, overseen planning and led the district’s education foundation, in addition to having been a teacher, assistant principal and baseball coach.

Beyond that, Howat has served on the Seminole State College board of trustees, appointed by two governors. Known to be seeking a superintendent post, Howat was a finalist for the Seminole County job in 2012.

Scott Fritz served as a teacher and administrator in Hillsborough schools from 1992 to 2008, when he moved to Osceola County as an assistant superintendent. He left that post after two years to become chief academic officer of Orange County schools, returning to Osceola in 2016 as chief of staff for teaching, leading and learning.

Fritz, who holds a doctorate from the University of Central Florida, was a finalist in 2017 to be Alachua County superintendent.

Sarasota County superintendent Todd Bowden was a principal and assistant principal in Hillsborough schools, with experience in adult and technical education that is again in vogue statewide. He’s had many conflicts with his current board, and his chief operating officer faces a whistleblower complaint that could land in Bowden’s lap, too. He might be looking.

Former Hernando County superintendent Lori Romano sits nearby in a mid-level administrative job in Pasco County schools. She was let go by the Hernando board, which criticized her for inefficient leadership, but has won accolades and promotions since moving to Pasco.

Looking out of state?

State Sen. Bill Montford runs the state’s superintendent association. He said that over the past decade, the demands and pressures placed upon school districts’ top leaders have grown, along with the responsibilities and requirements. That could cause “a lot of people to have second thoughts about entering into the role of superintendent,” Montford said. “It makes it more difficult to attract and retain top people to be superintendents in the state of Florida.”

That said, one name that gets dropped occasionally is that of Michael Hinojosa, a highly regarded two-time superintendent of Dallas, Texas, public schools who has brought stability to his hometown school system while improving its finances and its academic standing. Though he’s already retired once, and has a contract that runs through December 2020, Hinojosa’s name has been mentioned by a handful of wishful Hillsborough folks who would like to see him do here what he did for Dallas.

There’s Jesus Jara, as well. A one-time Monroe County superintendent and Orange deputy, Jara now heads the massive Clark County, Nev., school system. If he’s interested in returning to Florida — he grew up in Miami after moving from Venezuela — it wouldn’t be much of a change from running the sixth-largest district to the eighth.

The list is in no way definitive or even authoritative. It doesn’t include enough women, for instance. But it’s a starting point, based on a collection of conversations, as the district moves toward its next leader.