ST. PETERSBURG — A decade ago, as downtown was poised for a business and cultural renaissance, a young real estate developer bought one of the district’s most prominent buildings.

The historic Kress building sits at the northeast corner of Central Avenue and Fifth Street N, four stories above the intersection that, these days, is decorated with a bright rainbow mural. At 26, Samuel Ramzi Boutros had big dreams for the property.

“I’m going to make it more attractive,” he said at the time. “I’m going to be aggressive.”

In the years after he bought it, Boutros appeared online as a man about town. He sponsored events for the alumni association of his alma mater, the prestigious Canterbury School of Florida. He bought more properties around the city, plus a million-dollar house in Tierra Verde. His Facebook friend lists and photos include a handful of local politicians.

But more recently, Boutros has developed another reputation, whispered among service industry workers and tenants of his properties and backed up by a long, winding trail of court records.

Six people accused Boutros of inappropriate sexual behavior between July 2019 and April 2020, police and court records show.

Four were food delivery drivers who said Boutros was naked when they arrived at the Kress building. Another woman, who lived in one of Boutros’ residential buildings, said he pressured her to send him nude photos and have sex with him after she fell behind on rent. The other accuser was his ex-wife, who told police she found troubling videos on Boutros’ computer involving her daughter.

Each time, Boutros wasn’t arrested. With the delivery driver incidents, police struggled to pin down a crime: Did nudity in a private office count as indecent exposure?

But last spring, one of the delivery drivers complained to the St. Petersburg Police Department’s internal watchdog, sparking a review by a detective and the agency’s lawyer.

In August 2020, prosecutors charged Boutros with three counts of exposure of sexual organs and two counts of committing a lewd act, all misdemeanors. A judge put him under a court order to stop ordering delivery, and at least two delivery apps, GrubHub and DoorDash, deactivated his accounts.

Boutros did not return multiple calls from the Tampa Bay Times placed to his cell and business phone numbers. When a reporter tried to talk to him after a court hearing, he deferred comment to one of his attorneys. The lawyer, Lucas Fleming, said his client didn’t mean for anyone to see him naked but acknowledged the risk is higher outside the home.

“That’s the failing of this situation: not being sensitive to, or aware of, what can happen as a result of this behavior,” Fleming said.

Boutros denied that he pressured his former tenant to send him pictures and perform sex acts, Fleming said, and denied anything inappropriate regarding his stepdaughter.

By May, Boutros and prosecutors had struck a plea deal. But when they went to court, the judge balked. The proposed agreement included house arrest but no jail time.

“I don’t know what could sway me to think that jail wasn’t appropriate,” Pinellas County Judge Theodora Komninos said, according to an audio recording of the hearing.

The cases are now headed to trial in December, more than two years after this all began.

‘His modus operandi’

A DoorDash driver arrived at the Kress building the afternoon of Oct. 30, 2019.

The driver, 29 at the time, had an order for an office in unit M8. No one answered the door. She called the customer, and he told her to bring the order inside.

She didn’t think much of it — maybe the man had limited mobility, she thought — so she walked in.

A man police later determined was Boutros emerged from a back room, naked. He told her to shut the door, saying he had a tip for her.

“I just dropped the order and ran out,” she said in an interview. “I was terrified … I feared for my life.”

A similar pattern played out over several months. The Times is not naming the drivers or Boutros’ former tenant because they’re alleged victims of sexual impropriety.

In one case, a male delivery driver, 52, told police that he rounded a corner and saw a naked man come out of the bathroom into the hallway.

A few months later, a 30-year-old GrubHub driver heard a man say, “Come in, but I warn you” before she went inside. He told her he was a nudist, she told police.

In another case, a DoorDash driver, 60, picked up an order for “Sam B” from a pizza restaurant. A woman in the building warned her the customer was naked, but the driver didn’t think she was serious, she told police.

She heard a man’s voice say something like, “I got a tip for you if you deliver it yourself.” Inside the office, Boutros stood with his knee bent, holding $5. They joked about nude beaches, then she left.

“I went into shock as a survivor of a college sexual assault and a survivor of childhood sexual abuse,” she later wrote in a letter to police.

Boutros was in Sarasota during the first incident in October 2019, his criminal attorney said in court. Prosecutors said they can prove otherwise. In the other incidents, Fleming said the encounters were misunderstandings. Boutros warned the drivers, or asked them to leave the orders at the door.

“Many of them would still come in,” Fleming said. “I guess they want tips.”

The 60-year-old woman sued Boutros in November 2020, and they settled for $2,500. The driver declined to comment for this story. The settlement barred her from talking about the case and from pursuing prosecution.

Boutros sued her for breach of the agreement in April, accusing her of pressuring prosecutors to pursue the case. The suit is ongoing.

Meantime, more legal trouble stacked up for Boutros.

One of his tenants had fallen behind on rent, according to police and court records. The 28-year-old woman was living in an apartment at 511 Fourth Ave. S.

She moved out in February 2020, and Boutros said she could work for him at his Kress building office to pay her debt. He offered to pay her more if she worked naked.

She thought he was joking, but when she arrived March 4 for her first shift, Boutros wasn’t wearing clothes, the woman said in a federal lawsuit.

Her account is this: He asked her multiple times to undress. She said no. He asked if she could “at least take her top off.” She acquiesced. Over the next day, in person and over text, Boutros asked her for nude photographs. He threatened her with legal action when she refused.

When she questioned the threat, he said he was still willing to work with her, “but it was up to her how to proceed,” according to the lawsuit.

She never went back.

She reported the situation to police in March 2020 and sued him that May. They settled the lawsuit in March for $7,500, according to a copy of the settlement provided by Boutros’ attorney. When reached by the Times, the woman said she had been advised by her lawyers not to talk about the case.

This settlement also included a confidentiality clause and a section that said the woman had reviewed video and text messages that contradicted what she’d said in police and court records.

Boutros is facing criminal charges for three of the delivery driver incidents. But prosecutors believe there were eight other food delivery workers who had similar encounters and didn’t notify police, said Frank Piazza, county court division director for the Pinellas-Pasco State Attorney’s Office.

“This wasn’t a mistake,” Piazza said. “This is his modus operandi.”

They’re basing that on videos of those encounters found during a separate investigation. That one involved Boutros’ ex-wife and young children.

Trouble at home

Two years after he bought the Kress building, Boutros got married. His wife had a young daughter from a previous relationship, and the couple later had three children together.

The Times is not identifying the woman to protect the identities of the children.

In hindsight, she said in an interview, the red flags started almost as soon as the relationship did. He’d at times discourage her from seeing friends and family, she said. He started going out and drinking more, and his behavior became volatile. Boutros, through Fleming, denied that he treated her that way.

In July 2019, the couple got into an argument at home, according to a police report. She was holding their baby son and trying to record Boutros on her phone.

Boutros took the phone, grabbed her arm and pushed her, she told a Pinellas deputy, according to the report. The deputy noted she had a bruise just above her right elbow. He arrested Boutros on a count of domestic battery. Prosecutors later dropped the charge.

While her husband was in jail, she started rooting around his home office, she told a deputy.

The woman bumped into his desk, moving a computer mouse, which brought the machine out of sleep mode.

She found a trove of “obscene” videos that detectives described in police reports and an affidavit asking a judge to sign a search warrant to look for evidence of child pornography.

The house had a surveillance system with cameras in each of the children’s bedrooms and speakers the couple used to communicate with them. The network doesn’t have a storage system, so the videos are erased after about two hours — unless someone saves them, court records show.

On Boutros’ computer were 17 videos of his stepdaughter, who was 10 at the time, partially undressed or nude. Boutros denied he downloaded the videos and didn’t know how they got on his computer, Fleming said.

There was also a video of Boutros in his home office, masturbating. His stepdaughter pokes her head inside to say goodnight.

“You’re like, always right there,” he says, laughing. “I even thought I heard you.”

Detectives interviewed the three oldest children and found no evidence of physical or sexual abuse. Boutros’ stepdaughter told investigators she hadn’t seen anything when she came to his office door.

A search of the house and an investigation turned up nothing criminal.

In the home office video, it was unclear if Boutros covered up or continued touching himself, Sheriff Bob Gualtieri said. The videos of the stepdaughter in her bedroom didn’t constitute voyeurism because the cameras were known to the children and in plain sight.

“Unfortunately, the law doesn’t cover all the varied scenarios when people do bad stuff,” Gualtieri said. “Obviously, the situation is concerning, and everyone should be concerned by it.”

The girl’s mother was horrified.

“So what, they have to physically be molested?” she said. “This is already abuse.”

The woman sued Boutros on behalf of her daughter. The lawsuit is ongoing.

The videos also caught the attention of a judge overseeing the couple’s divorce, which Boutros filed for a week after the raid.

“I have seen tens of thousands of cases over 15 years,” Pinellas-Pasco Circuit Judge Cynthia Newton said at a January 2020 hearing, “and I can tell you something pathological is going on here, and it’s very disturbing. … The court has very, very serious concerns for the safety of not just the (stepdaughter) but all children in the home.”

Newton would later remove herself from the case after Boutros filed a motion saying her comments meant she was biased.

The parents worked out a settlement and a parenting plan, and a new judge finalized the divorce in April 2020. The plan allowed Boutros to see his children with supervision for six months, then unsupervised after that.

Fleming pointed to the settlement as a vindicating moment for his client.

“All these incidents were known, discussed with a therapist, discussed with the court, talked about during the divorce case,” he said. “He was obviously able to do well enough in that process to have a judge say you’re good to go with your kids.”

‘I want people to know what he’s doing in that building’

With each delivery driver report, responding officers took a few steps to investigate but didn’t make arrests. They wrote in reports that they couldn’t find the customer or confirm Boutros’ name through the delivery apps, or that being nude in a private office wasn’t a crime.

One driver, from the incident in October 2019, said officers more or less laughed off her report.

“The way they were acting was, they weren’t taking it serious that this was a predator,” she said.

Another said officers didn’t ask for a statement or more information.

“I want people to know what he’s doing in that building,” he said.

The officer in the April 2020 incident started putting the pieces together. He noted the prior reports and calls, including the one involving the former tenant.

He took the woman’s statement, then went into the Kress building as Boutros was coming out. They interviewed him outside the building. Boutros said he enjoyed working naked. He said he warned the driver, and she came in anyway.

When asked about the other incidents, the officer wrote, Boutros got upset. He said some weren’t true, and some were because he was a nudist. He said he wouldn’t do it again.

“It is believed that the suspect is gaining some type of sexual fulfillment by these nude interactions,” wrote a detective who reviewed the case about a week later.

Still, the detective wrote, the case didn’t rise to indecent exposure because Boutros never left his private office.

About two weeks later, one of the drivers sent a letter to police questioning how officers had handled her case. Among other complaints, she wrote that a supervisor told her it was her fault for walking into the office after she was warned.

“I had his food, and I didn’t want to be accused of stealing,” the woman explained in the letter. “There was a lot at stake other than the needs of Samuel Boutros.”

All four cases were reexamined in May 2020.

The department’s in-house attorney “spent a great deal of time” researching prior cases, police spokeswoman Yolanda Fernandez said. She found examples of an interpretation of the law that could support charging Boutros. Prosecutors agreed.

They didn’t pursue charges in one of the cases because they couldn’t reach the driver to see if she wanted prosecution, records show. And, while Boutros’ former tenant reported her case to police, she told the officer she didn’t want to press charges.

“We believe that ultimately justice prevailed,” Fernandez said.

Over the next several months, Boutros and the Pinellas-Pasco State Attorney’s Office negotiated a deal. In return for pleading guilty, Boutros would serve 120 days of house arrest and three years of probation with a curfew. Other terms of the sentence included participation in a sex offender treatment program; no access to or viewing of pornography; warrantless searches of his house, computers and car; and annual polygraph exams.

“This sentence isn’t really a slap on the hand,” Piazza, the prosecutor, said. “It’s a pretty harsh sentence.”

The deal became moot when the judge struck it down. Boutros could face several years of jail time if convicted, Piazza said.

In March, nearly a year after the last delivery driver incident, Boutros was back in his office in the Kress building.

He ordered a drink from the restaurant on the ground floor, a woman who used to work as a bartender there told the Times. Through Fleming, Boutros denied this encounter occurred.

She walked the drink up to his office.

It was trashed, she said, with papers strewn everywhere. She told him he needed to get organized. He said he’d been looking for someone who could help him with that. The woman said she could probably do it.

He asked if she had a problem with nudity.