The immigrant advocate pressed Pinellas County Sheriff Bob Gualtieri as he stood with his empty cup of coffee. He quickly told her why she was wrong.

“That’s not true,” he said. “That’s just not true.”

They spoke outside a committee room in Tallahassee, Gualtieri in town that morning in part to support a sanctuary city ban that he had helped craft.

The bill had attracted substantial opposition, with people warning of constitutional rights violations and eroding trust between immigrant communities and law enforcement.

The debate had been playing out for years, and Gualtieri had his playbook ready.

He’s not concerned about undocumented immigrants living quiet, law-abiding lives, he told the advocate that day in March. He threw out, instead, one of his go-to examples: Sergio Martinez, an immigrant from Mexico who, by the time he was convicted of sexually assaulting two women, had been deported 20 times.

“There’s so much to this,” he said.

They talked about meeting again but with a condition.

“If you guys could be informed and educated,” Gualtieri said, “I’d love to sit down.”

The sheriff has a low tolerance for anything other than the facts, or, his detractors would say, his interpretation of the facts.

He took his seat inside, where the bill would sail through the Florida House Civil Justice Subcommittee. The sheriff sat conspicuously among the suits, in a forest green uniform, a Glock on his hip.

In this city — where Florida’s laws are created — Gualtieri, 57, has become a formidable force, one lawmakers bow to and activists seek out, knowing his opinion holds weight.

Gualtieri, a Republican, was recently named Sheriff of the Year by a national association representing 3,000 sheriffs.

He’s emerged as a law enforcement leader on immigration, forging closer relationships with federal authorities and pushing for the ban, one of Gov. Ron DeSantis’ most hardline campaign promises.

Gualtieri’s decision not to arrest a man who shot a father in a convenience store parking lot last summer set off a national debate about stand-your-ground laws.

And he spent the last year leading a commission formed in the wake of the Parkland massacre, pivoting his own view and landing at what was perhaps the most controversial legislation this session: creating a pathway to allow certain teachers to carry guns.

It’s no coincidence that Gualtieri is a 6-foot-5 lightning rod in the middle of the most polarizing issues in America.

• • •

Gualtieri addresses the House Civil Justice Subcommittee in Tallahassee about the sanctuary city ban. He was a force in the bill's passage. [Courtesy Liberty Partners]
Gualtieri addresses the House Civil Justice Subcommittee in Tallahassee about the sanctuary city ban. He was a force in the bill's passage. [Courtesy Liberty Partners]

The committee hearing was the beginning of Gualtieri’s long day in Tallahassee.

In between meetings were impromptu exchanges, invitations and thank yous.

The sheriff discussed the issues of the day with a memory so sharp it seems at times photographic.

His scholarly attention to details and intense work ethic have been constants through a meandering career: from law enforcement to law school to private practice and back.

He traces his love for policing to his childhood in Syracuse, N.Y.

Gualtieri’s late father, Frank, worked as a district attorney in the 1970s. Grade school Gualtieri would go with his dad to work on Saturdays in an office across the street from the police department. He had friends whose dads were cops.

“It just kind of got on the radar and never left,” the sheriff said.

In 1980, he moved to Florida with his family and the next year, when he was 20, he applied to work as a corrections officer at the Sheriff’s Office.

“Inspires confidence,” a sergeant wrote after Gualtieri’s first interviews.

“Maybe over-aggressive,” a deputy thought, “seems like the John Wayne Syndrome is in effect here,” referring to a hero complex named after the actor who played tough cowboys in old westerns.

He was hired in 1982 and eventually landed in the narcotics unit as a detective, where he made a name for himself specializing in wiretaps through the ’90s. He didn’t shy away from the tedious report-writing and time-consuming nature of the investigations.

“He was probably the hardest working guy out there,” said Dale Jones, a former Pinellas sergeant who supervised Gualtieri.

In 2000, he enrolled at Stetson University College of Law with an interest in prosecution and to escape a feeling of stagnation. Gualtieri, a poor student in his teens, graduated with honors and landed a job at Ford Harrison, a national labor employment firm with a Tampa office. He was among the firm’s highest billers as a new lawyer, said Tracey Jaensch, a regional managing partner who supervised Gualtieri and still keeps in touch.

Jaensch recalled a complex case where the firm was supporting Pinellas’ firing of a paramedic accused of falsifying information on a report. Gualtieri studied the medical literature ahead of an administrative hearing with the vigor typically reserved for a trial.

The Pinellas sheriff at the time, Jim Coats, kept tabs on his former detective, and eventually, he offered him a job that mixed the law degree with the badge: general counsel.

A few years later, Coats stepped down to care for his ailing wife, and with his blessing, former Gov. Rick Scott appointed Gualtieri to the top job in 2011.

At the next election, Gualtieri drew a daunting opponent for the primary nomination, which would all but clinch a win in a county with a 30-year history of Republican sheriffs.

Everett Rice, a well-respected former sheriff, had name recognition, key endorsements from police unions and more money in his coffers.

But Gualtieri’s campaign had a strategy.

“He has such presence,” said Ed Armstrong, a longtime Clearwater land use lawyer and Republican power broker. “He’s such a hugely principled guy. If we could get him out there … and give people exposure to him, we felt they’d feel very, very good about him.”

Fifty-seven percent of Pinellas Republicans agreed.

• • •

The sheriff stepped toward a lectern and looked up at the TV cameras.

“So, at about 3:30 yesterday afternoon,” he began, “the Pinellas County Sheriff’s Office responded to the Circle A convenience store.”

He told the story now known around the country:

On July 19, 2018, a man named Michael Drejka approached a driver who had parked her car in a handicap-reserved space without a permit. The two argued. The driver’s boyfriend, Markeis McGlockton, stepped out of the store and shoved Drejka to the ground.

Drejka, 48 and white, pulled a handgun and fatally shot McGlockton, 28 and black, once in the chest. The exchange was caught on a store surveillance camera.

From the lectern, fewer than 24 hours later, Gualtieri made the shocking announcement that he would not arrest Drejka, saying his hands were tied.

He spent half an hour explaining how he applied Florida’s controversial stand-your-ground law to this case, winding through legal jargon and choice words about the deceased.

“Markeis wouldn’t be dead if Markeis didn’t slam this guy to the ground,” he said, “so Markeis has got skin in this game, too.”

ORIGINAL STORY: No arrest in fatal shooting during argument over handicap parking space

After the news conference, rage spread across social media, fueled in part by the races of those involved, and followed by a rapid succession of vigils and calls to action. Many officials would have laid low, but Gualtieri took to the mic again.

This time, he talked for 55 minutes, packed with indignation that the case “has gotten twisted around in so many ways.”

Days after Michael Drejka shot Markeis McGlockton, the Circle A Food Store became a memorial. [DOUGLAS R. CLIFFORD | Times]
Days after Michael Drejka shot Markeis McGlockton, the Circle A Food Store became a memorial. [DOUGLAS R. CLIFFORD | Times]

The cloud over the Sheriff’s Office got worse when The Rev. Al Sharpton came to town to call for Drejka’s arrest.

Once again, the sheriff piped up.

“I don’t really care what Al Sharpton has to say,” he said during an unrelated news conference. “Go back to New York. Mind your own business.”

Upon reflection, the sheriff acknowledged he may have said too much about his decision not to arrest Drejka. And the Sharpton remarks?

“I can see where it may not have been the best thing to say, to not do what he was doing, which was to ramp it up,” he said. “But also I think people like him, who are doing that, need to get called out on it, and people need to say, and not be afraid to say, we’re not going to tolerate that here, either.

“I might say the same thing again.”

TIMELINE: The Markeis McGlockton case, from shooting to stand your ground furor to shooter’s arrest

• • •

Gualtieri’s office sits on the third floor of the Sheriff’s Administration Building off Ulmerton Road. His desk has an organized chaos to it.

Stacks of legislative paperwork recently sat near a DVD on the Columbine High School shooting and an inbox shelf overflowed with manila folders.

“If I don’t get through it every day, it gets ugly,” Gualtieri said, amid conference calls, debriefs on criminal investigations and a Human Resources review of applicants from deputies to crossing guards.

For all the long hours, Gualtieri hardly shows it. His appearance and mannerisms have the worn rigidity of a textbook spine. He usually wears black shoes, always shiny, and intense expressions, while his fingers tap tables or fidget with pens.

“Bob runs the Sheriff’s Office like the CEO of a company,” said Kevin Hayslett, a longtime defense attorney and former prosecutor.

And it’s a behemoth: about 3,000 employees with a $300 million budget. His duties include oversight of the county jail, with an average daily population of about 3,000 inmates. He makes about $172,000 a year.

Some in the rank and file see him as a micromanager. The critique is compounded by the fact that he had little supervisory experience before landing the top job.

“He's very hands-on from my experiences with him, and that can be good or bad, depending on what the situation is,” said Bruce Bartlett, the chief assistant prosecutor at the Pinellas-Pasco State Attorney’s Office. “Perhaps sometimes the staff is a little intimidated, being careful about what they do and how they do it, because they know they're going to be looked at very closely."

Ideologically, Gualtieri can be hard to pin down.

He is a red-state sheriff, who voted for President Donald Trump, but he’s enacted programs that are seen as progressive.

As chief deputy, he helped open Pinellas Safe Harbor, an emergency shelter next to the county jail to divert homeless people from the criminal justice system.

After becoming sheriff, he expanded the use of diversion programs for kids and launched a program for adults. He started a bond program with electronic monitoring for those who struggle to make bail.

And he formed a mental health unit that pairs deputies with social workers.

Years ago, Gualtieri opposed an open carry bill, leading Marion Hammer, a powerful lobbyist and a former National Rifle Association president, to call him out in an alert to members. Pro-gun advocates accused him of betraying the Second Amendment.

Fast forward, and he’s become the face of the proposal to arm teachers, which is NRA-supported. He took twice to NRATV to talk over the idea with show host and national spokeswoman Dana Loesch.

The segments, more measured than the network’s typical inflammatory programming, aired in the middle of an already potent rebuke to the idea from teachers’ unions, gun control groups and, polls show, a majority of Floridians.

Beyond the policy stances, Gualtieri’s self-described blunt demeanor can come off as lacking empathy.

The remarks about McGlockton’s role in his own death come to mind, said Michele Rayner-Goolsby, a Clearwater civil rights lawyer representing McGlockton’s parents. So do the deaths of three teenage girls who drowned in a stolen car that plunged into a pond in 2016, she said.

Gualtieri included posters with their mug shots and criminal histories during a news conference to underscore the severity of a car theft epidemic still playing out in Pinellas County.

Clearwater lawyer Michele Rayner-Goolsby has sparred with the sheriff over several high-profile cases. Here, she speaks to the media the week after the fatal shooting at the convenience store. [DOUGLAS R. CLIFFORD | Times]
Clearwater lawyer Michele Rayner-Goolsby has sparred with the sheriff over several high-profile cases. Here, she speaks to the media the week after the fatal shooting at the convenience store. [DOUGLAS R. CLIFFORD | Times]

Rayner said she feels the sheriff has allowed unexamined internal biases to seep into his decision-making and interactions with the public.

“There are ways to speak about people with humanity,” she said.

Isabel Sousa-Rodriguez, membership and organizing director with the Florida Immigrant Coalition, notices the same pattern when it comes to the sheriff and immigration issues.

“He's trying to do this whole good immigrant, bad immigrant thing,” Sousa-Rodriguez said. “It’s really dehumanizing.”

Those who have challenged him have left the room feeling he was dismissive, condescending, maybe even vindictive.

Last year, Gualtieri requested a meeting with Steven Hirschfield, who runs the breaking news website IONTB.

The sheriff was concerned Hirschfield, a former Sheriff’s Office volunteer, had accessed an agency system.

“So I do what I do,” the sheriff recalled. “I called him in and as opposed to beating around the bush, I was direct with him.”

Hirschfield explained his news gathering methods, none of which included what Gualtieri accused him of. The sheriff took him at his word, Hirschfield said, but added that if he found out otherwise, they would have a problem.

Hirschfield found the meeting intimidating and bizarre.

James McLynas, the sheriff’s most vocal critic and a 2016 sheriff candidate who has also filed to run in the 2020 election, contends the sheriff arrested him on phony charges as revenge for filing complaints against deputies and trying to expose misconduct in the agency.

His distrust of Gualtieri stems from a personal feud involving McLynas’ estranged wife.

The sheriff writes off almost everything connected to McLynas, who has no law enforcement experience, as “nonsense.”

Even those who support Gualtieri say there is little room for discussion once he’s made a call.

His wife, Lauralee Westine, said he wrestles with decisions, particularly the ones that impact people’s lives.

She said she and her husband both have Type A personalities, blowing through to-do lists with mechanical precision, although she is more of an internal decision maker.

Gualtieri circles around each step, gathering information until he’s ready to move. It can be exhausting living in a world where a family ski trip to Utah is planned with the same exactness as a SWAT arrest. But just look at the results, he’ll say.

“Did you have a good time?” Gualtieri, all tongue and cheek, recently asked Westine and their 13-year-old daughter, Lauren.

“Yes,” they both said.

“Just checking.”

• • •

Pinellas-Pasco Circuit Judge Lauralee Westine, left, and her husband hang out with their daughter, Lauren, 13, while taking their dogs MacDuff and Graham outside. [DOUGLAS R. CLIFFORD | Times]
Pinellas-Pasco Circuit Judge Lauralee Westine, left, and her husband hang out with their daughter, Lauren, 13, while taking their dogs MacDuff and Graham outside. [DOUGLAS R. CLIFFORD | Times]

On a recent Sunday, Gualtieri answered the door at home in black gym shorts and a purple Nike crewneck. He and Westine, 48, gave a tour of the first floor, but the conversation quickly turned to the dogs.

There’s MacDuff, a German shorthaired pointer; Sandy, a lumbering Lab; Wags, a white maltese; Graham, a black terrier mix; and Oliver, a Havanese mix who technically belongs to Gualtieri’s mother-in-law but who is “here, like, 99 percent of the time,” Gualtieri said.

There are also four rabbits: Bun Bun, Charlie, Mr. Brown and Alfie, who live on a patio with a plastic playhouse and garden of hay and alfalfa seed they share with a guinea pig, who Westine calls “Aggressive Young Male Guinea Pig.”

Mr. Brown is one of four rabbits among the herd at Gualtieri's home in East Lake. [DOUGLAS R. CLIFFORD | Times]
Mr. Brown is one of four rabbits among the herd at Gualtieri's home in East Lake. [DOUGLAS R. CLIFFORD | Times]

The cats, Thai Thai and Cookie, are down from the original four because “we’re on the attrition plan now,” Gualtieri said.

“We’ve been on the attrition plan since we got married,” Westine jabbed back.

In this jurisdiction mostly run by dogs, Gualtieri insists that he likes them, even as he not once leaned down to pet one. Still, they used to have a furless, partially blind pekingese named Bella and one morning, as Gualtieri was about to go to work, she fell into the pool. He leaped in after her. His suit was ruined, but the women of the house were happy.

The family lives with the herd in a 7,500-square-foot, five-bedroom, six-bath home in East Lake. The front door opens to a Mediterranean-style foyer with a view to the backyard patio and pool overlooking the Tarpon Woods golf course.

Hang a left, and a hallway leads to what the women call the “man cave.” Gualtieri spends his evenings there, lounging on the brown leather couches, surrounded by sports memorabilia, and flipping between Bay News 9, CNN and Fox.

Gualtieri watches news reports and home improvement shows in his man cave. [DOUGLAS R. CLIFFORD | Times]
Gualtieri watches news reports and home improvement shows in his man cave. [DOUGLAS R. CLIFFORD | Times]

When he can’t take the rhetoric anymore, he turns to HGTV. He likes House Hunters, Fixer Upper and Property Brothers, but his favorite is Caribbean Life, which makes sense when you learn that he takes solo vacations to Puerto Rico to do nothing but work out and take long walks on the beach.

His weekend release is cardio and weightlifting at the LA Fitness in Dunedin, amid driving Lauren to early swim practice, dropping off dry cleaning and hours posted up at a Panera with more work.

Family photos all over the house show some of the other women central to his life. He has two daughters from a first marriage, and he grew up with four sisters.

One of them, Joan, died at 19 after she was hit by a drunken driver on Gualtieri’s birthday in 1983. His parents died young, too, his mother, Linda, at 55, and father, Frank, at 58, both of cancer.

Gualtieri and Westine, a former prosecutor and land use lawyer turned family circuit court judge in Pasco County, rely on Westine’s mother to shuttle Lauren back and forth to school and weekday swim practice.

But Gualtieri and his daughter go to Tampa Bay Lightning games, even taking a trip to Toronto in March to watch the Bolts defeat the Maple Leafs.

The hockey obsession started with one of his older daughters, Christina, now 28. They’d go to games multiple times a week, she remembered.

Now a lawyer living in Atlanta, she’s struck by how well her dad balanced fatherhood and law school. She recalled he used to pick up her and her older sister, Jordanna, from gymnastics in the evening, grab them dinner and himself a giant coffee from Starbucks, then study into the night.

Their parents’ divorce in 1995 felt seamless, too, the sisters said, and they remain close to both, plus Lauren and Westine. Gualtieri’s ex-wife could not be reached for comment.

Gualtieri and Westine met when he was on a DEA task force and she was an intern at the U.S. Attorney’s Office. Her St. Pete house was broken into, and afterward, she told Gualtieri she wanted to get a gun for self-defense.

He took her to Bill Jackson’s, so she could try one out. Then he asked her to dinner. Westine dressed casually, thinking on a student budget.

Instead, he showed up in a suit and announced he had made reservations at Oystercatchers in Tampa.

“I said, ‘I’m going to need a minute,’ ” Westine recalled.

They married at the restaurant in February 1998. Lauren arrived in 2005.

Nowadays, he runs the concession stand at Lauren’s swim meets with the same attention to detail he embodies professionally.

He brings a toaster from home to heat up the everything bagels the masses demand, even if he would never eat something that onion-forward in the morning.

The family's Sunday night ritual involves dinner at Vetture's Pizzeria and Restaurant. [DOUGLAS R. CLIFFORD | Times]
The family's Sunday night ritual involves dinner at Vetture's Pizzeria and Restaurant. [DOUGLAS R. CLIFFORD | Times]

• • •

Gualtieri was in Washington, D.C., for a Major County Sheriffs Association meeting last year when a sheriff beside him looked down at his phone.

“You got a school shooting in Florida,” he said.

Gualtieri looked to see where, then thought to himself, “Here we go again.”

Back home, lawmakers quickly got to work on a sweeping school safety package that included forming a state commission tasked with investigating the shooting. Gualtieri was named chairman.

“I knew Bob would take it seriously,” former Gov. Scott said in an interview last month. “He would put in the time, and he would get everybody’s input in a thoughtful manner.”

Gualtieri, right, responds to a question during a meeting of government leaders days after the Parkland massacre.[SCOTT KEELER | Times]
Gualtieri, right, responds to a question during a meeting of government leaders days after the Parkland massacre.[SCOTT KEELER | Times]

One of Gualtieri’s first moves in the new role was to take a tour of the crime scene.

He saw the blood on the floor, the papers still on the desks, the shoes left behind from the chaotic escape.

It “was one of the worst things I’ve ever done,” he said.

So he understands all the emotions, even if he rarely shows it. But he can’t understand those who argue only from emotion. He has a phrase for those arguments: “parade of horribles.”

He wishes he could get a million people in a room, so he could fully explain why he supports the idea of arming teachers who would volunteer and undergo intensive training. It goes, in broad strokes, like this: School shootings start and end so quickly and often involve current or former students who can come and go easily. In the face of an inevitable next time, there must be another line of defense.

Former Gov. Rick Scott selected Gualtieri to lead the Marjory Stoneman Douglas High School Public Safety Commission. The sheriff came to believe that trained, volunteer teachers should have access to guns so they can stop shooters who get past other safeguards. [AP file]
Former Gov. Rick Scott selected Gualtieri to lead the Marjory Stoneman Douglas High School Public Safety Commission. The sheriff came to believe that trained, volunteer teachers should have access to guns so they can stop shooters who get past other safeguards. [AP file]

What everyone should be asking themselves, he said, is whether they’ve done everything they can to effect change. He has, he said, and he’ll make it clear if he feels you’re standing in the way.

Take the president of the Florida chapter of Moms Demand Action for Gun Sense in America, who said his demeanor was dismissive when the group has tried to raise concerns. Gualtieri pushed back and said the same could be said for them.

“Is that being dismissive of their position or I just don't accept their premise?” he said.

He is flat-out offended at any implication that he has racial bias. And he thinks the justice system is generally fair, though he acknowledges that socioeconomic factors can play a role in crime.

“I have a lot of empathy … but I’m also not going to do anything different just because somebody happens to be of a certain race or national origin. I’m not going to coddle somebody. If you’re a criminal, you’re a criminal.”

He continued: “Are there more people of certain races or national origins that are criminal justice-involved than others? Yes. I don’t think there’s any doubt about that. Is it because the policies or the laws or the system are unfair to them, or are they more involved in it for other reasons? And I tend to believe it’s for other reasons.”

He said he sees the three girls who drowned in the stolen car as victims of their circumstances as well as criminals. He also brings up the diversion programs and social services he’s led or put in place as evidence of his compassion.

Omali Yeshitela, founder of the Uhuru movement, St. Petersburg, called for Gualtieri's resignation because of how the agency handled the 2016 drowning deaths of three teenage girls. [SCOTT KEELER | Times]
Omali Yeshitela, founder of the Uhuru movement, St. Petersburg, called for Gualtieri's resignation because of how the agency handled the 2016 drowning deaths of three teenage girls. [SCOTT KEELER | Times]

When asked about weaknesses, the sheriff stumbled.

“It’s not that I don’t have weaknesses,” he said. “Of course, I do, but I’m trying to figure out what matters.”

Sometimes, his compassion is a weakness, he said, such as when he’s given someone a shot who didn’t deserve it.

He knows he could be a better listener and more tolerant of those who don’t work with his intensity or pace.

He doesn’t apologize for being hands-on as a manager. He sees it as his responsibility.

His involvement in immigration and gun debates is purely practical, he said. He spots a problem, and he finds a solution, and if that means he gets cozy with politicos sometimes, so be it.

It’s here, as sheriff, where he feels like he can make the biggest difference.

He plans to run again in 2020.

Other offices he’s been rumored to be working toward, such as attorney general, and one he actually considered in 2013 — the late C.W. Bill Young’s congressional seat — he’s not so sure.

So, he’s doing all of this out of the goodness of his heart? A cynical mind would say that sounds like a bunch of crap, no?

He laughed, rigid indignation melting away.

He gets it, he said. He does.

But it’s the truth.

• • •

On the same morning an Orlando-area TV station flashed a story of a school safety bill barreling through the Legislature, the man behind parts of it was close by, barreling east on Interstate 4 on the hunt for coffee.

He found a Panera about 15 minutes down the road from the Volusia County Sheriff’s Office training facility, where he was scheduled to give a presentation to dozens of cops from multiple agencies.

Volusia Sheriff Michael Chitwood introduced him to the packed room.

“This presentation and report that he does is absolutely remarkable. It’s a story of epic failures. It’s a story of cowardice. And it’s a story of heroism,” he said. “I think you’ll leave scratching your head, saying ‘How the hell did this happen? How can we make sure that it doesn’t happen here?’ ”

Gualtieri moved through Feb. 14, 2018, with no script, no peek at the screen, a nonstop three hours with the same rage as if the shooting had happened the week before.

He talked to the cops with an insider’s touch: “you all have experienced it” or “you guys know.”

And yet, he was making a pitch, talking up the importance of arming teachers and pushing other proposals his commission embraced.

Afterward, Magalis Maldonado, a Volusia school resource deputy, reeled from the details and from Gualtieri’s presence.

She knew he was a sheriff, she said.

“But then I thought, maybe he was more than that,” she said.

“More like a politician.”

Gualtieri speaks to dozens of cops in Volusia County about the Parkland shooting and the public safety commission's findings. He's given the same talk across the state. [KATHRYN VARN | Times]
Gualtieri speaks to dozens of cops in Volusia County about the Parkland shooting and the public safety commission's findings. He's given the same talk across the state. [KATHRYN VARN | Times]

Times senior news researcher Caryn Baird contributed to this report. Contact Kathryn Varn at [email protected] or (727) 893-8913. Follow @kathrynvarn.