Drugs, guns and politics collided in the small town of Port Richey. Two mayors went to jail.

PORT RICHEY — Month after month, police officers headed to the big blue house on the water.

They had often been called there by the home’s owner, one of the most prominent people in Port Richey: the mayor, Dale Massad.

Many calls were about two women in his life. Massad told the police one spat in his face, the other threatened to plant drugs in his home and he wanted both to go away. At times all three lived together at the house; they got into fight after fight, year after year.

Other calls described thefts, trespassers and strange occurrences. Once, while telling an officer about a missing gun, the mayor added that a bag of marijuana had appeared in his desk drawer, only to vanish mysteriously the following day.

Police came to Massad's house more than 50 times in the three years he was mayor.

Then in February, a SWAT team burst through Massad’s door to arrest him on charges of practicing medicine without a license. Massad fired two rounds from a handgun. He was charged with attempted murder.

A Tampa Bay Times examination of the mayor’s rise and fall shows that his growing instability was in plain sight of the city’s leaders. But for nearly two years, none of them moved to determine the extent of his problems or to curtail his influence in the city.

Several had unusual entanglements with the mayor. City Attorney James Mathieu owned and operated a rental property with Massad. City Council member Richard Bloom prescribed Massad’s girlfriend Prozac at the mayor’s request without physically examining her. City Manager Vincent Lupo gave Massad a high-powered pistol, then separately wrote the mayor a $1,200 check while Massad was under criminal investigation.

Officials across city government acknowledge noticing that the mayor seemed out of it in some public meetings. And in interviews with the Times, Lupo and police Chief Gerard DeCanio described a trail of troubling incidents dating back years. But it wasn’t until last summer that they told the Florida Department of Law Enforcement what they knew about the mayor.

Even after his arrest and resignation, powerful people in the city kept looking out for Massad. His successor, Vice Mayor Terrence Rowe, talked with Massad about the need for someone in the city to pay for starting the investigation. “I’m on it,” Rowe said. Shortly after, Rowe was arrested and charged with conspiracy to obstruct justice.

Rowe declined to comment, as did attorneys representing Massad.

The jailhouse phone call was the culmination of a cozy relationship between the two men that had been years in the making, emails between council members show. In one, Rowe reacted with elation to the news that a project to dredge canals — a topic Massad was obsessed with — was about to begin.

“WAHOO!!!!” Rowe wrote. “Pinch me, I must be dreaming.”

Rowe suggested that Massad and Lupo meet him to celebrate. “Champagne at Dale’s?”

[ More on this: What Port Richey’s elected leaders really think, and other deleted scenes from our investigation ]

Massad had problems long before he appeared in Port Richey.

Late one morning in July 1992, a Pinellas sheriff’s deputy found Massad sitting on the sidewalk outside a Palm Harbor strip mall. He was shirtless, slurring his words and clutching a pistol.

Rounds from the gun were scattered on the ground. Massad, then 41, said he’d been in a fight with his girlfriend. He had no ID but explained who he was: a laser surgeon.

The deputy didn’t buy it. Massad “was unshaven, had no shoes or shirt on, and had dirty fingernails and hands,” the deputy wrote in a report.

Massad was indeed a laser surgeon. But his medical license was in jeopardy. In 1990, he started laser treatments on a 3-year-old girl to remove birthmarks that covered her body. Massad “did not recognize” reactions the child was having to an anesthetic during a procedure he oversaw, according to state medical board records. The girl died.

The chairman of the state licensing board called Massad a threat to the public. Massad surrendered his license in November 1992.

[ Weird Florida stuff: The long, odd history of Pasco County politicians behaving badly ]

Massad didn’t stop showing up in police reports. A confidential informant told Pinellas County narcotics investigators that Massad was associating with a suspected coke dealer. An anonymous tipster said Massad also might be dealing drugs. And a girlfriend told a deputy he gave her a black eye, but she didn’t want to press charges.

In 1999, Massad moved from Palm Harbor to Port Richey. A year later, he was appointed to an empty seat on the City Council.

Port Richey is a city of 3,000 people, home to blue-collar retirees and wealthy professionals who want to live on the water. It has no downtown, an annual budget of nearly $12 million and a reputation for incompetence that has led to talks about dissolving the city six times.

Massad told people to pronounce his name like “acid” with an “M.” He described himself as a retired doctor, adding “Dr.” or “M.D.” to his signatures. In Port Richey, everyone came to know him as Doc.

His primary income came from an annuity, according to financial disclosure forms he filed with Pasco County. He would later tell state agents a disability policy paid him about $19,000 a month.

Massad was elected to two-year council terms in 2002 and 2006. Around then he was showing up in police reports multiple times a year. The most serious allegations were domestic abuse.

In 2004, Massad’s then-fiancée told police he grabbed her by the throat and swung her around after she refused to have sex with him. In 2008, a different woman accused Massad of assault. She had first reported that three black men raped her at Massad’s home, but later told police it was Massad who sexually assaulted and battered her.

Massad denied abusing both women and said they had punched and slapped him. Police said there wasn’t enough evidence to arrest Massad in either case.

Two months before the 2015 election — with Massad running to be mayor — his girlfriend called the police. She said people were hiding in the air-conditioning vents of Massad’s home. Officers found Massad searching for the intruders with a flashlight and a loaded gun. He said he’d been partying but denied using drugs. No intruders were found.

Then-City Manager Tom O’Neill gave the police report to the City Council. Nonetheless, Massad was elected mayor with 182 votes.

He became the city’s ceremonial leader and started running council meetings. He was re-elected unopposed two years later.

By then, officers were going to his house about 17 times a year.

The calls often revolved around two of Massad’s on-and-off girlfriends. Police reports depict the women as drunk or on drugs. Massad kicked out each at least once, and took out two restraining orders against one of them. But he always let them come back.

Last year, a domestic dispute with one of the women led to both Massad and the woman being arrested on battery charges. Prosecutors didn’t pursue either case.

Some of the clashes put the city police department in the position of investigating ambiguous abuse allegations made against the city’s leader.

In May 2016, one of the women told Port Richey officers that he shoved her into a wicker partition and kicked her knee. She had accused him of abuse before. Three days later, she recanted.

A police sergeant asked her if anyone was forcing her to recant, and she started to cry.

The sergeant asked whether Massad had promised her anything, such as housing or money or drugs, if she took back the allegations. She cried harder.

The sergeant said the police could try to protect her.

“You can’t protect me,” she said under her breath.

She left the police station. The case against the mayor was closed. She was arrested and convicted on charges of making a false report.

Around Port Richey, Massad was known as a charismatic leader who hated red tape and spoke his mind. He once called state environmental regulators “dumb bureaucrats who have nothing better to do than count seaweed.”

Massad repeatedly proposed dissolving the city’s police department and outsourcing the work to the sheriff. He wanted the savings to dredge canals, which would largely benefit waterfront property owners like himself.

He bickered with some council members, and his views weren’t always popular.

But Massad bonded with Lupo, the city manager, starting when he was a council member. In 2001, Lupo joined the board of a nonprofit called Africare Enviro-Med, which aimed to provide medical care in Africa while also fighting poaching. Massad was the president.

Lupo said they couldn’t get the charity off the ground, largely because of restrictions on pharmaceutical imports and exports.

But it still allowed Lupo and Massad to go hunting in Africa. The pair took three trips there in just over a year, allowing Lupo to successfully hunt the Big Six — an elephant, rhino, hippo, Cape buffalo, lion and leopard.

Lupo threatened to end a recent interview with the Times when asked how he financed the hunting trips. He said he paid for the trips himself and did not write them off on his taxes.

In 2004, Massad lost a re-election campaign. The new council fired Lupo, in part because he hired a building official who lacked the proper state license.

Lupo told the Times he and Massad fell out of touch. But Lupo still went to the party celebrating Massad’s election to the council in 2006, according to a Times column from that year.

Massad also developed a relationship with another top official. In 2007, Mathieu, the city attorney, became co-owner of a house with Massad. The two bought out Massad’s previous co-owner, jointly took out a mortgage and have rented out the property ever since, Mathieu told the Times in a recent interview.

“Beyond that, I really don’t have a relationship with him,” Mathieu said. “Everybody thinks we’re friends. But we don’t socialize.”

Massad lost a re-election bid in 2008. The new council fired Mathieu.

Not long after Massad rejoined the council as mayor in 2015, both Mathieu and Lupo returned to Port Richey.

Massad had clashed with O’Neill, the city manager who circulated the police report about the people in Massad’s vents. When O’Neill quit in 2016, Massad lobbied for Lupo to return. Lupo was rehired that August.

By then, Massad’s outlandish behavior was well-known. The incident with the air vents had been reported in the Times, including a comment Massad made to the responding police officers: “If I was you, I would think I am crazy too.”

Five months after Massad’s election, he got into an argument with a resident during a City Council meeting. The resident objected to pink fliers Massad had used during his campaign to attack other city politicians, including the recently deceased mayor who preceded him. Massad heard the word “pink” and said he thought the resident was calling him a communist. “You’re in a fog,” the resident told him.

[ Read C.T. Bowen’s take: Why is nobody surprised at Port Richey Mayor Dale Massad’s downfall? ]

Lupo told the Times that Massad seemed like a different man than the one he knew during his prior stint with the city.

At some point, Lupo recalled seeing a kitchen cabinet packed with pill bottles in Massad’s home.

“What the hell are you doing with these?” Lupo said he asked Massad. “Are you crazy?”

Lupo told Massad to “get a plastic bag, dump all of this stuff in there and get rid of it — unless it has your name on it.”

But Lupo didn’t tell police about the pills. He waited until the state investigation launched, then told agents he thought Massad was distributing the medication.

Asked by the Times whether he should have reported the information sooner, Lupo said, “Not really. I thought it was a very personal thing. I thought what he was doing was altruistic. It was not significant in my mind. The guy was a doctor at one point.”

Lupo told the agents he tried to distance himself from Massad. The mayor was hanging out with “the dregs of society,” Lupo told state investigators, and his actions grew “increasingly bizarre.”

But he still visited him frequently to explain city business and to help him prepare for council meetings.

And he gave the mayor a gun.

It was a CZ 52 pistol, which fires rounds that can pierce body armor.

The gift was detailed in a police report. In May 2018, Massad called Lupo to tell him that three guns had been stolen from his house. Lupo reported the theft to Port Richey police and added that in 2017, he had given Massad one of the guns: the CZ 52.

Massad would later tell police that he had found the other two guns in his house but not the pistol from Lupo.

During the missing-gun investigation, the police also interviewed Bloom, the City Council member, because he’d recently visited Massad’s house. Bloom told police Massad showed him guns from his collection. But when officers later asked Bloom to provide a written statement, the councilman said a judge would have to order him to do so. Bloom told the Times he saw no point in the statement because the guns had been found.

That wasn’t Bloom’s only link to Massad. One of Massad’s associates told state investigators that Bloom — a doctor and malpractice lawyer — prescribed Massad’s girlfriend Prozac. The associate told agents he drove Massad’s girlfriend to Bloom’s house to get the prescription.

Bloom denied to the Times that Massad’s girlfriend was driven to his house but did say he prescribed her Prozac once. He said Massad called and asked him to write the prescription because she was going through withdrawal and could not reach her doctor.

In interviews Monday and Tuesday, Bloom said he prescribed the medicine without examining the girlfriend based on his conversation with Massad. “I took his analysis of her,” Bloom said.

Bloom said he did not ask for proof that Massad’s girlfriend had a prescription but described Prozac as “benign.” He said he was comforted by the fact that Massad had medical training. “Once a doctor, always a doctor,” Bloom said.

State rules bar Florida doctors from writing a prescription without evaluating the patient, including conducting a physical exam and documenting the patient’s medical history. They also say telemedicine — which usually consists of exams conducted via video — cannot be practiced over the telephone.

Later Tuesday, Bloom called back to add that he did speak with the girlfriend on the phone before writing the prescription and performed a “superficial” mental health evaluation that showed signs of serious Prozac withdrawal. In an email Wednesday, he pointed to a provision in state rules on telemedicine that allow exceptions in medical emergencies.

By the end of 2017, City Council member Jennie Sorrell said Massad’s deterioration was clear enough that she worried about his ability to do his job. Some of Massad’s statements during council meetings didn’t seem grounded in reality, Sorrell said.

“His home life is such a mess,” she remembered thinking. “How can he run the city?”

Councilman William Dittmer told state investigators Massad would say things that were “off-the-wall” and that it seemed the mayor was having a hard time functioning or thinking clearly in council meetings.

Lupo said some statements Massad made during city meetings led him to question whether the mayor had a substance problem. The mayor also started telling Lupo to fire specific city employees, Lupo told state investigators. Lupo said he didn’t follow Massad’s instructions.

In September 2017, Massad missed a coffee meeting related to his job as mayor, according to an email Rowe sent chiding him.

“If you are going to do this, you need a dedicated person to see that you remember,” Rowe told the mayor. “It looks really bad and they get more angry every time. I know, OOOPs.”

Despite her concerns, Sorrell said she felt like she had few options on a five-person council where Massad, Bloom and Rowe often voted together. She opted not to ask questions. “I didn’t want to know, because I’d have to do something about it,” she said. “I guess I was avoiding it.”

Port Richey police kept receiving information about Massad.

In April 2018, they got a tip that a suspect in a shooting had bragged about selling drugs at Massad’s home, according to police reports.

That July, WFTS-Ch. 28 reported on police visits to the mayor’s home. The station interviewed Massad at City Hall. Massad, wearing dark sunglasses, told the reporter on camera that the police report about the people hiding in his vents was “way embellished.”

Massad also cheerfully told the reporter about the time he shot a smoke detector inside his home to make it stop going off.

But it wasn’t until August that the police chief, DeCanio, felt his department had firm-enough allegations to justify a broader investigation into the mayor’s behavior.

That was when two witnesses accused the mayor of performing medical procedures inside his home, DeCanio said. They said they had pictures.

DeCanio said he met with Lupo and briefed him on the witnesses and other evidence against the mayor. Lupo decided to turn the case over to state agents, DeCanio said.

Lupo handed the lead investigator a flash drive with 59 police reports involving Massad. He told the investigator that the mayor’s actions had become unacceptable.

State agents spent five months investigating Massad.

In early February, a few weeks before Massad’s arrest, Lupo wrote the mayor a $1,200 check.

Lupo told the Times the check was to purchase a gun that an acquaintance had given Massad as collateral for a loan.

The city manager said he scribbled on the check the serial number of the weapon — a .45-caliber pistol — along with a description of the purchase and the acquaintance’s initials. State investigators later seized the check when they raided Massad’s house.

Lupo said he saw nothing wrong with the transaction.

“What’s so wrong with that? Think about it,” he said. “There’s nothing wrong with that. It has nothing to do with anything.”

One of Massad’s friends told investigators that the day before the raid, he overheard Lupo warning Massad he was still under investigation. Lupo told Massad he should clean up his house and his act, the friend said.

Lupo told the Times he didn’t recall that conversation and didn’t know when agents would serve their warrant. But he said Massad knew about the investigation and had talked to him about it. Lupo said the friend isn’t trustworthy, and noted he has a drug arrest.

Lupo said he didn’t know how Massad found out about the inquiry. Both Lupo and DeCanio said they assumed it was because people in Massad’s circle were being interviewed.

During the period when top officials were visiting the mayor’s 3,200-square-foot house on the water, criminals were hanging out there as well, people close to Massad told state investigators.

Vagrants and drug pushers described floating through the mayor’s home, snorting lines of meth from a marble countertop.

Massad smoked crack nightly, a witness told agents. The witness said he bought the mayor $100 worth of the drug five nights a week.

Massad liked crystal meth, too, according to four witnesses. He called it “jet fuel.”

The mayor also provided medical care to people he knew, they said. Massad performed procedures at the house, sometimes on his kitchen table, according to investigative reports that describe at least six specific examples.

One witness said he saw Massad working on another man’s toe injury “like you would see in a hospital,” using a suture and an injectable anesthetic.

“You didn’t see anything,” Massad told the witness, a handyman who had never been to the mayor’s home before, according to a summary of his interview with investigators.

The handyman said one of Massad’s comments left him in fear for his life: “We take one-way fishing trips around here.”

SWAT deputies from the Pasco County Sheriff’s Office stormed Massad’s home before dawn on Feb. 21. They pounded on his door, sounded their siren and threw a flash-bang inside. Massad fired two shots from a .40-caliber pistol.

Deputies say Massad shot toward them. Massad’s lawyers said that he didn’t know who was outside and was firing warning shots.

But on the morning of his arrest, Massad told sheriff’s deputies something different.

He did know the people at his door were police, the deputies wrote in a report — he just believed they worked for Port Richey.

Within a day of Massad’s arrest, Lupo and the city attorney visited the mayor at the Pasco County jail with resignation paperwork. Massad signed it.

Lupo told state investigators Massad repeatedly called him to discuss city business while in custody. Lupo told the Times he gave the former mayor the following advice: “Read books. Get yourself healthy. Watch television. And forget about the city.”

But Massad couldn’t.

He called Rowe, then the acting mayor, from jail late at night on March 3. Before Rowe came to the phone, a recorded message announced the line was being taped.

“Hey, man,” Massad said. “It’s treacherous out there.”

Massad started dictating plans for city business to his successor. He walked Rowe through the minute details of a $155,000 bid for a project to dredge a canal. Massad said he had just talked to Lupo and told the city manager that he was a “f--king idiot” if he didn’t kick one of his administrators “in the ass.”

“You guys can use my name, if it’s worth a shit,” Massad offered.

“You’re famous,” Rowe replied, laughing.

“You know what my charges are, right?” Massad asked.

Massad answered himself: “Five counts of premeditated homicide.” Then he snickered.

Massad asked Rowe what the news coverage had been like. “How bad are they whacking me?”

“Oh my god, Doc.”

Later, Rowe said he’d been telling everyone: “You have just witnessed a political assassination, a bloodless coup.”

Over the course of the next eight minutes, the two discussed a range of topics. Massad told Rowe that it sucked in jail. He said he tried to call Bloom, but Bloom didn’t answer. The ex-mayor described the city police department as unchained, mentioned he paid $350,000 for his attorney and said he no longer wanted to be a politician.

For about 70 seconds in the middle, they talked about the origins of the investigation. Massad brought up the Port Richey police officer who went undercover to bust him. Rowe said he was ready to make sure someone was held accountable.

“Just be careful,” Massad told Rowe. “They will throw you under the motherf--king bus. I’m just glad you’re not quite as flamboyant as I am.”

On March 5, Rowe began digging into the officer’s background, according to state agents.

Port Richey’s new mayor was arrested a week later.

Contact Rebecca Woolington at rwoolington@tampabay.com. Follow @rwoolington. Contact Justin Trombly at jtrombly@tampabay.com. Follow @JustinTrombly. Data reporter Connie Humburg contributed reporting and data analysis to this report. Times staff writers Caryn Baird, Bethany Barnes, Neil Bedi, C.T. Bowen, Martin Frobisher, Kathleen McGrory and Eli Murray also contributed reporting.

[ Want more on the two mayors? Click to read the deleted scenes: What Port Richey’s elected leaders really think, and other deleted scenes from our investigation ]

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