Ron DeSantis took the long way in naming Raymond Sandelli as Lee County Commissioner

The long-awaited appointment of a new Lee County Commissioner came with little fanfare Friday.

Gov. Ron DeSantis announced real estate broker Raymond Sandelli would be sworn in this week. He broke the news in neighboring Charlotte County, at the end of a news conference chiefly about a new Red Tide Task Force.

The news felt almost anti-climactic to those unaware of months of speculation and jockeying around the choice.

Officials in the Governor’s Office say DeSantis acted meticulously and carefully in considering his choice for the job.

“More than one candidate was interviewed for the position of Commissioner of Lee County, and Gov. DeSantis chose the best candidate: Raymond Sandelli,” said Helen Aguirre Ferre, DeSantis’ Director of Communications.

“Mr. Sandelli is a veteran, former Blue Angel, and successful businessman who did not seek this position but accepted the call to serve. He is a selfless leader and understands the commitment to community.”

In fact, sources close to the process say DeSantis bounced around several potential picks before recruiting and settling on the business leader.

At various times, at least four other candidates nearly got the job.

One of them — Christin Collins — claims she was told a news release would come out within hours before a last-minute campaign against her spoiled her chances.

But she was just one candidate who felt close to landing the job.

Sudden vacancy

The saga of Lee County’s open seat started in April with the death of Lee County Commission Chair Larry Kiker.

The news did not come as a total surprise; Kiker missed a series of meetings due to health problems, but he held onto his seat for some time hoping to return to service. He entered hospice care shortly before the end of his life.

Kiker entered into politics in 2012 after defeating longtime County Commissioner Ray Judah in a Republican primary. Four years later, the incumbent barely won reelection after facing a primary challenge himself. But leaders celebrated his legacy when he died.

Within days of Kiker’s passing, hopeful successors came forward to replace him, wrongly presuming DeSantis would make a quick choice.

But many figured the contest over when Paula Kiker, the commissioner’s widow, applied for the job and filed to run for the seat in 2020. Paula Kiker had been a fixture on the campaign trail beside her husband, bringing an intimate understanding of issues.

Inside the Governor’s Office, however, sources say little consideration was given to Paula Kiker.

DeSantis worked to establish himself as an environmental champion, but Larry Kiker wasn’t a favorite of conservationists. Knowing Kiker won reelection by less than 1,000 votes in 2016 suggested to the Governor that the late pol was no giant of Lee County politics.

Add that Kiker had long been criticized for being too cozy with Big Sugar, an interest DeSantis battled for years, and DeSantis felt no pull to his widow.

But without simply picking Kiker’s ideological and life partner, the seat represented a chance for a significant political move. How could the chance be used?

Negotiation chit

The open commission seat came as political jockeying was already underway in Lee County for another office.

Three of four state representatives living in the county cannot run because of term limits, and state Sen. Lizbeth Benacquisto‘s seat was also opening in 2020.

State Rep. Ray Rodrigues ultimately emerged as the heir apparent for Benacquisto. But state Reps. Dane Eagle and Heather Fitzenhagen also considered runs.

Senate President-designate Wilton Simpson, though, made it clear he did not want to see an expensive Republican primary during a year when control of the chamber could be at stake.

After Rodrigues announced he would run, Eagle immediately endorsed him. But Fitzenhagen held out and remains the only member of the Lee County Legislative Delegation yet to endorse anyone.

Sources say Simpson approached Fitzenhagen to warn a primary would be rough. Senate and House leadership preferred Rodrigues, ensuring vast financial resources for his bid.

But Senate leadership didn’t just try to threaten Fitzenhagen out of the way. They also tried to lure her with a different appointment. Why not apply for the Lee County seat? Should this route have been taken, a special election would be held to fill Fitzenhagen’s House seat, per Florida law.

If the theoretical special election had gone to Jenna Persons, a candidate already running for the seat and leading in fundraising. That could allow Persons to run as a redshirt incumbent in 2020.

In the end, Fitzenhagen didn’t sign up for that plan. She told Florida Politics in May she would not run for Senate nor apply for County Commission.

But the episode made clear forces in Tallahassee saw how the appointment could be used to other ends, and that the pool of candidates would not be limited to those who applied for the job.

Prosecutor and business choice?

As weeks passed, another contender became a favorite of many Republican leaders in Lee County. Matt Roepstorff, a former prosecutor with connections to the Republican Executive Committee, became a choice for many establishment leaders.

Jonathan Martin, chairman of the Lee County Republican Party, endorsed Roepstorff privately and publicly.

“He is a solid guy,” Martin said. “He’s young. He is conservative. He has a lot of knowledge on how things work and how the local economy works.”

In early June, he seemed a lock for the job, sources close to the governor said. Within days of Florida Politics’ article about Martin’s support, DeSantis visited Lee County and said he would make a pick “relatively soon.”

Developer Pat Neal, a former state lawmaker who represented Lee County and remained closely involved in politics there, said he believed three weeks ago Roepstorff was almost certain to get the job. Martin hoped so as well and didn’t know precisely when the Governor started to shift away from that choice.

But sources say groups like Captains for Clean Water started pushing against Roepstorff as a choice, believing he would value business over water in a sensitive area.

The Southwest Florida-based conservation group has enjoyed a close relationship to DeSantis since his election. Focused on business and water quality, the relationship has been a mutually beneficial one. For DeSantis, it gives the Republican governor credibility on green issues.

Capt. Daniel Andrews, the group’s executive director, did not confirm heavy lobbying efforts about the Lee County appointment and said the group focuses more on state policy. But he did suggest a level of dissatisfaction with the status quo in Lee County.

“I think the Commission as a whole can do a better job as far as looking our for the environment and do anything they can to slow down the rate at which we pave out wetlands,” he said. “That’s just common sense.”

On top of all that, Roepstorff works now for GrayRobinson, a prominent law and lobbying firm, and that appointment could bring its own ‘optics’ issues for DeSantis.

Support began to amass around an alternative choice, one from outside traditional politics. But it still wasn’t Sandelli.

Another choice

Just as a Roepstorff choice seemed imminent, a groundswell started toward Collins.

As a system health and wellness partner at Lee Health, Collins in 2017 won the Person of the Year award from The News-Press in Fort Myers. Charlotte Newton, a former editorial board member at the paper, wrote a guest column in June openly lobbying DeSantis to choose Collins for the commission.

“She has demonstrated time and again her commitment and passion for improving the quality of life for all,” Newton wrote.

Andrews also had good words to say about Collins.

“Christin is a good friend, and I heard she was being considered,” he said. “I saw she was talked about in the paper. Maybe she will run in the next election.”

Front-runner status shifted from Roepstorff to Collins. After a final choice was made, Collins claimed in an email to friends and supporters that DeSantis’ people told her at one point she had the job.

She wrote that on June 11, DeSantis’ Chief of Staff Shane Strum told her a news release was in the works and could come out within hours. Sources say Roepstorff was also told the Governor chose Collins.

Before a release hit inboxes, however, staff for DeSantis told Collins they needed to make calls to a couple of prominent GOP donors in the area.

But as Collins prepared herself for phone calls and a new career in politics, the ground shifted again. When Strum called her back, he had new questions.

“He immediately asked if I had hosted fundraisers for Democratic candidates,” Collins wrote. She had not, but did share that in 2018, she’d written a check to Nikki Fried, now Florida’s Agriculture Commissioner.

That wasn’t good. Fried was the lone Democrat in 2018 to win statewide office in Florida, defeating Lee County Republican Matt Caldwell. And she did so after a contentious recount process and by a historically close margin.

The race had been so close that Caldwell declared victory on Election Night, and among hard-core Republicans in his hometown, it’s still conventional wisdom — true or not — the Lehigh Acres Republican got robbed of the job.

DeSantis and Caldwell have never been tight, but he had issues appointing a Fried supporter. While the Governor and Agriculture Commissioner have a collegial relationship at Cabinet meetings, Fried is likely to challenge DeSantis in 2022.

Strum also posed a strikingly more personal question to Collins.

A Naples Daily News article had been rapidly distributed about a speech Collins gave at a Planned Parenthood event in 2016. At the event, Collins shared the story of how in her early 20s, she had gone to a Planned Parenthood branch for birth control.

Instead, she ended up being diagnosed with ovarian cancer. Strum asked Collins to explain her views on abortion.

“I calmly began to explain that the County Commission does not make decisions regarding this issue. But regardless, I expressed that I do not sit in judgment of pro-life/pro-choice,” Collins wrote in her email. “Many decades ago, I was robbed of the opportunity to have children, and I choose not to judge others.”

She then said she supported Planned Parenthood because the organization literally saved her life performing emergency surgery on her at age 21. She tried to tell the story, but Strum cut her off, saying he already knew it from the article.

When the conversation ended, Strum told Collins to sit tight and wait for the release to come out. But no announcement ever came. “I never heard from Shane again,” she wrote.

The Governor’s Office disputes this. They say DeSantis indeed interviewed multiple people for the job, but none of the top prospects learned of the final choice without a courtesy call.

“As is always the case, the candidates who were interviewed and not chosen were called and thanked for their time and interest in being considered for public service,” Ferre said.

Sources in Lee County politics characterize the emailed account from Collins as sour grapes. Regardless, moving past Collins meant the DeSantis team again had to start from scratch.

Familiar Faces?

Despite having dozens of applicants, the Governor’s office wanted to find someone else.

The office reached out to Eagle, who serves now as House Republican Leader. At one point, Eagle acknowledges, there was a discussion of giving him the job.

The Cape Coral Republican ran for office in the area first in 2012, the same year Kiker beat Judah, and he easily won election to office four times in seven years in the area. Eagle also helped much of DeSantis’ legislative agenda get passed this year.

But Eagle demurred when it came to the County Commission appointment.

“It was brought up,” Eagle said, “but it was not a job I was interested in. I told them I wanted to finish my time in the House.”

So if not Eagle himself, who did the Lee County Republican recommend? Eagle set out to make reasonable suggestions. He didn’t have to look very far.

Eagle in his day job works as a broker associate at CRE Consultants, which just happens to be where Sandelli works as managing partner. The two have a long professional relationship and friendship.

“The Governor was looking high and low, and they had a good list of people who applied but didn’t take the decision lightly,” Eagle said.

Eagle asked Sandelli about the job, Sandelli had served in the military, and maintained an interest in public service. Plus, he actually lived in Kiker’s county commission district and could run for election if he chooses.

Sandelli said he felt honored by the outreach.

“I was a little bit surprised,” Sandelli said. Sandelli didn’t know Kiker well but had attended his funeral. He does know fellow County Commissioners Brian Hamman and Cecile Pendergrass.

“I thought Dane would take [the appointment], honestly, but he already has a job. So I said I would put my name in and we would go from there.”

Sandelli soon found himself on the phone with DeSantis himself. In the span of a few weeks, the broker went from being recruited to apply, to being interviewed for the job, and then surfacing as DeSantis’ choice.

The talk with DeSantis went well, and the next thing he knew, DeSantis offered him the post. The Governor praised Sandelli at a press conference, and noted the fact the businessman had not lobbied for the job.

“He is not somebody who sought out the position,” DeSantis said. “But he is very capable and community-minded.”

Captains for Clean Water represented attended the event where Sandelli was announced, but showed up knowing the Red Tide Task Force would be announced. Andrews said no one from the group knew DeSantis would announce the Lee County Commission choice at the event.

Neal said Sandelli represented a solid choice who should please both business and conservation interests in the region: “Ray has a heroic personal status, a nice family, a business background.”

Sandelli serves through next November. He said he has not yet decided if he will seek election.

But sources close to DeSantis believe the Governor would not pick someone for the job that had no intentions of sticking around long-term.

Ferre stressed the Governor had deliberated extensively, and acknowledged he strongly considered several people for the job.

“Matt Roepstorff, state Rep. Dane Eagle and state Rep. Heather Fitzenhagen are fine candidates and were considered for the position,” she said. “Gov. DeSantis made his choice and the position was offered to Raymond Sandelli.”

That list notably omits Collins.