Dale Massad met up with a SWAT team in Port Richey.
All illustrations by Nico Teitel

The Strange Rise and Sudden Fall of the Florida Mayor Who Took on a SWAT Team

A disgraced doctor and alleged user of crack and meth managed to take over a city until he got caught. Somehow, that was just the beginning.

Before dawn on February 21, a squad of Pasco County deputies in tactical gear and heavy weaponry emerged from a massive armored vehicle, known as a Bearcat, on a quiet road near a massive house with a sweeping backyard view of a bayou connecting to the Gulf of Mexico. The five-member SWAT team crept to the front door of the waterfront estate, according to a Pasco County Sheriff's Department arrest report.


The Bearcat's blue and red lights and blaring siren pierced the serenity of Hayward Lane, a quiet residential street in Port Richey, a small city on Florida’s west coast. A sergeant pounded his fist on the front door of the two-story home, shouting, "Sheriff's Office! Search warrant! Come to the door!"

No one answered.

The sergeant banged again—one, two, three, and four times, announcing himself. Still nothing. He tried yet again, screaming the same command, his fist drumming the door five times. No response from inside the house.

The sergeant stood aside as two of his squad mates took position: One of them, cocking a shotgun, blasted off the door's locks. The other, lugging a battering ram, bashed the door. Once inside, officers set off a flashbang device.

A few seconds later, two loud pops rang inside the home. The SWAT team retreated, ducking for cover behind the Bearcat. An officer shined the vehicle's spotlight on the second floor window, where police spotted a middle-aged man with wiry graying hair. He gripped a .40 caliber pistol in one hand and a cellphone in the other.

The incident might sound like just another Sunshine State absurdity, but the shooter was no ordinary Florida man. He was Dale Massad, at the time the mayor of Port Richey, and a character whose brazen lifestyle has come into fuller view since he was arrested and charged with attempted murder in connection with that episode. Press reports, court records, and interviews describe an elected official whose personal life spiraled out of control as he engaged in a romantic relationship with a woman who was jailed three times for allegedly assaulting him, while welcoming into his home petty thieves with long rap sheets who allegedly supplied him with a steady diet of crack and meth. Regular visits by the police to his home were followed by his advocating the dissolution of the local police department, a policy stance he has since argued put an even bigger target on his back.


Even in the post-Rob Ford era, the image of a drug-addled, gun-toting mayor blasting bullets at cops busting down his door is so absurd that it got its moment in the national spotlight. But it's also a reminder that, even as national politics dominates headlines everywhere, Americans' daily lives are often most affected by their local governments. And like the rest of the country, those governments are occasionally run by oddballs, charming incompetents, and outright criminals.

'It reflects on fucking America. I was mayor and they came in at 4:30 in the morning for no reason.'

Florida alone has more than 400 cities, towns, and villages, each with its own mayor and commissioner types. And with so many fiefdoms that garner little to no ethical oversight, it’s especially easy for grifters, kooks, and other unqualified individuals to win local elections. The population in Port Richey was 2,739 when Massad was elected in 2015—about 60 percent were eligible to vote, but only 26 percent turned out to the polls. Of the 449 Port Richey citizens who voted, 182 cast ballots for Massad. He got 20 more votes than the second place finisher. And just like that, a guy who'd end up in a firefight with the cops was running the town.

"Small groups can be very successful in getting out the vote and bringing out unusual candidates," said Peter Cruise, executive director of Florida Atlantic University’s Leroy Collins Public Ethics Academy, adding, "Florida has a terrible record of not paying attention to local races."


Indeed, it often seemed like no one paid attention to Port Richey during Massad's strange time within the local power structure, which dates back to 2002. But for a small town unaccustomed to a ton of outside scrutiny, the SWAT raid was just the beginning of Port Richey’s dirty laundry being put out to dry.

Dale Massad

Dale Massad sat behind a bullet-proof glass window in a concrete room of the Land O' Lakes Detention Center, the local jail near Florida's Gulf Coast run by the Pasco County Sheriff's Office. His former status as Port Richey’s mayor hadn't won him any special privileges: Shortly after his arrest and before being interviewed, jail deputies tasered and forced Massad to the ground, according to a motion filed by prosecutors.

The ex-mayor, prosecutors said, was kicking and thrashing at the guards, and was tased when he refused to comply with their commands. ("We felt it was completely unnecessary," Denis deVlaming, Massad's attorney, said in an interview. "He was in his cell when it occurred. He was having an episode and they tasered him.")

Despite his colorful personal life, cops hadn't show up at Massad's house on February 21 because of any violent or recreational tendencies on his part, at least not directly. Agents from the Florida Department of Law Enforcement (FDLE) called in the heavy artillery to help gather evidence that the former physician was treating patients, even though he had relinquished his medical license more than two decades ago. When the smoke cleared, Massad was arrested and charged for attempted murder of five Pasco County deputies, as well as the original crime they wanted him for: practicing medicine without a license. He could spend the rest of his life behind bars. (Massad has pleaded not guilty to all the charges against him.)


Meanwhile, Caj Joseph, Massad's girlfriend who was also in the house that day, was booked into county jail on charges of gun possession by a convicted felon. Inside the home, officers said, they recovered five shotguns, four handguns, and five rifles, including two AR-15s. In the master bedroom, they confiscated a stethoscope, a blood pressure monitor, a syringe, an EKG machine, and other medical equipment and supplies, according to an evidence list. Denied bail and suspended from office by Republican Governor Ron DeSantis, Massad quickly resigned as mayor.

'We've been to his house like 50 times in the past three years.'—Port Richey Police Chief Gerard DeCanio

A tall man with wide blue eyes, Massad sported a salt-and-pepper five o'clock shadow when interviewed in jail. His shoulders sagged in orange-and-white prison scrubs—the word "INMATE" was stenciled across the back—and his hands were handcuffed. A pair of stone-faced deputies stood guard, with one of the officers training a video camera on the disgraced politician.

"I grew up in Oklahoma, raised with the spirit of America and being free," Massad said. "I am finding out these things are not true anymore. These guys look at me like I am a dog."

His voice was hoarse, and he spoke in a low, rumbling Southern drawl. His eyes grew wider as he compared his predicament to the tribulations of the billionaire real estate mogul occupying the White House. "[President] Trump has a way of putting it when you get put in a negative light by the media," declared Massad, a registered Republican who—like most Florida mayors—technically ran as a nonpartisan. "Fake news! That's what you guys got."


During a 45-minute interview in March, Massad spoke at length about the split-second decision that cost him his elected office and his freedom. He agreed to talk knowing that the Pasco County Sheriff's Office would video record our meeting—and that any recorded statements he made could be used against him. Massad was eager to deliver his side of the bizarre standoff with cops: To hear him tell it, he was the victim of a "tenuous" relationship with local law enforcement during his on-and-off again stints on the Port Richey city council.

That the relationship was rocky is one point he and local police can agree on.

"We've been to his house like 50 times in the past three years," Port Richey Police Chief Gerard DeCanio said. "Everybody told him on more than one occasion to change the people he hung out with."

The grandson of a Lebanese immigrant, Massad said he relocated from Oklahoma to Gainesville, Florida, in 1976, landing a one-year residency at a local hospital's emergency room shortly after graduating from medical school. In his first 13 years as a physician, he never had a complaint filed against him, and spent five of those years running a hospital emergency room, according to online health department records.

But on August 22, 1990, his pristine medical career started flatlining. At the time, Massad resided in Palm Harbor, another Gulf Coast city about 15 miles south of Port Richey. A laser surgery on a three-year-old girl to remove skin discolorations known as "port wine stains" went horribly awry. A dentist, brought in by Massad to act as the anesthesiologist because the affected area was around her mouth, injected the little girl with lidocaine that turned out to be a lethal dose. She had a seizure and turned blue, but Massad didn't have any oxygen in his office. Precious minutes passed before paramedics arrived to take the patient to the emergency room, according to a Florida health department complaint. The child died three days later.


The health department charged Massad with practicing substandard medicine and failing to notice early signs that the child's life was in danger. In October 1992, Massad voluntarily surrendered his license, and the girl’s family received a $300,000 settlement. In a 1998 Sun-Sentinel story, Massad expressed remorse for the death: "I'm the captain of the ship. That's the bottom line. If I could be where that child is and let her be alive, I'd do that."

During the jailhouse interview, Massad didn't back away from accepting responsibility for the death. "I told her mother I would give her all the money I had," he said. "I decided not to fight the thing."

Leaving behind the havoc in Palm Harbor in 1999, Massad resettled in Port Richey, where he bought the waterfront house for $151,000, according to the Pasco County property appraiser's website. "I just went up the coast and found this place," he said. "It wasn't a really wonderful house, but it was a beautiful lot."

Over the years, he remodeled the property to his liking. At the time of the raid, the five-bedroom home featured an elevator that took riders from the second-floor down to the ground level that led to a game room, pool, patio, and separate guesthouse. The garage fit up to five cars, along with two boat docks, a boat lift, a fish-cleaning station, and a boat ramp. According to Zillow, the property was worth an estimated $601,820 as of early June.


Massad said he supported himself with a retirement investment fund, and that life by the water in Port Richey was more affordable than waterfront neighborhoods in other Florida coastal cities. "I live on the bayou," he said. "I have fishing. I have everything I need. I have skiing."

Around 2000, Massad carved a new path, launching his political career when friends encouraged him to seek an appointment to a vacant seat on the Port Richey city council. He still introduced himself to residents as "Doc." Two years later, voters gave him another two-year term when he was among the first three top finishers in a five-person race. "I got into politics in Port Richey and God help me," Massad said. "I always felt like I do something. And I think I did."

In 2004, Massad lost his re-election bid, but voters put him back on the council two years later. In 2008, he lost again, and stayed out of Port Richey politics for the next seven years. But in 2015, again goaded by friends, Massad said, he ran for mayor in a special election, and won.

Throughout his political career, Massad campaigned on a promise, among other pitches, to secure funding for the dredging of 25 canals in Port Richey. In 2017, the city council voted to spend $272,875 to dredge the first waterway, helping begin to realize his dream for the community even as his personal life spiraled. "Port Richey has the least expensive waterfront property on the coast," Massad explained in jail. "As soon as we get these canals dredged, people will be rushing to get into the city."


Of course, when he launched his run for mayor four years ago, Massad's home life was already a troubling cocktail of chaos and criminal activity.

Illustration by Nico Teitel

Police seized a bevy of guns, along with some medical equipment, at the time of Massad's arrest.

On August 6, 2015, just over two months before the election that put him in the mayor's office, a police officer responding to a call from Massad's house wrote in a report that the ex-doctor was in the master bedroom holding a gun and looking down an air conditioning vent, according to the Tampa Bay Times.

Three men were hiding in the vents and spying on him and his girlfriend while they had sex, Massad told the cop. The officer asked the ex-doctor if he'd been drinking or using drugs, according to a police report cited by the paper. Massad was said to reply, "You know I like to party, but I would tell you if I was."

Massad's female companion that day admitted to doing "a small line of cocaine" but declined to answer if he had ingested narcotics, the report said. The officers didn't find any intruders.

A review of police incident reports and other court records suggests Massad often enjoyed the company of some of Port Richey’s less-than-reputable inhabitants. His live-in girlfriend Caj Joseph has been arrested at least 21 times in Pasco County since 2011, picking up five felony convictions during that period. Among the charges the 58-year-old woman pleaded guilty to was battery on Massad: On June 4, 2017, Joseph punched the mayor and struck his leg with a car door.


Joseph was sentenced to nine months in county jail, after which she and Massad appear to have reconciled. In late August of last year, the couple were both arrested on charges of domestic battery against one another. They spent the night in jail, but the charges were dropped. Reached on her cellphone, Joseph said her lawyers advised her not to speak to the press.

Joseph wasn't the only person living on Massad's property who was regularly on the radar of local law enforcement. For a few months between 2017 and 2018, a drifter named Corey White moved into Massad's guesthouse, agreeing to pay $400 a month in rent. A 50-year-old man, White has been arrested for alleged battery on a pregnant woman, burglary, harassment, cyber-stalking, shoplifting, and criminal mischief since 2016, according to Pasco County jail records.

White's troubles filtered onto Massad's property. On January 24, 2018, White called police claiming a woman broke into the guesthouse and stole $80 and three prescription bottles containing Xanax, morphine, and oxycodone. Massad, speaking to the responding officers, backed up White's account. The then-mayor said he saw a woman and another individual standing near the guest house in the early morning. He gave them a warning, "'I have a gun,' and they ran off," according to the incident report.

The friendship between the men apparently soured soon after. By sometime in April of the same year, according to court records, Massad filed an eviction lawsuit against White for allegedly failing to pay rent since February.


One day last October, however, Massad found White passed out on his back porch and called the cops. White woke up, grabbed a towel, and took off before officers showed up, according to an arrest report. When cops caught up with him, White was arrested for alleged burglary of an unoccupied dwelling. Attempts to reach White were not successful—his last known phone number was disconnected.

Word of Massad's troubles reached city hall over the years, but his council colleagues and top administrators seem to have enabled the then-mayor's bad behavior. City Manager Vincent Lupo gave Massad a pistol in 2017 that was allegedly among three guns stolen from the waterfront home a year later, according to a police report described in a May Tampa Bay Times story detailing the mayor's exploits. Lupo told the newspaper he once saw one of Massad's kitchen cabinets stocked with prescription pill bottles that were not under his name. Lupo advised the mayor to trash the bottles and didn't report what he saw to the police until FDLE launched its investigation.

Lupo was more forthcoming with what he knew about Massad after the state policing agency began its probe into the mayor's alleged illegal medical practice. Another Tampa Bay Times story identified White as one of two informants who helped kick that process into gear by telling police they saw Massad treat people's injuries—and provided him with illegal substances. The ex-mayor's former tenant told police last year that he bought drugs for his landlord around 60 times, mostly crack cocaine and meth. He said he witnessed Massad smoke both and that the mayor would use runners to buy his dope to avoid getting caught.


DeCanio, the Port Richey police chief, confirmed he received a tip from people who lived in the mayor's house that he was practicing medicine without a license. To avoid any potential conflicts of interest, DeCanio said, he passed along the tip to the FDLE, which deemed the information credible. One source claimed to police that Massad removed a fishing hook from their back and supplied a cortisone shot, and another witness said Massad stitched up a deep laceration in the ankle, according to a criminal complaint. Massad's patients have not been identified.

"My relationship with [Massad] was good," DeCanio said. "He supported me. But I have a duty to act on the information. I can't sweep it under the rug."

Massad, on the other hand, expressed a nonchalant attitude about the alleged activities occurring on his property. He said he didn’t judge those who entered his strange abode, either. "I am not going to call the police department to get their rap sheet," he grumbled. "If you are in Pasco County, every other person is a criminal. I don't ask people about their past if they come into my house. But no one was a murderer or a rapist or anything like that."

When asked if he misused illegal substances and alcohol, Massad offered a coy response. "Listen, I am a child of the 60s," he said. "Do I do drugs now? No. Have I done them? Yes."

The FDLE probe picked up steam on September 29, 2018, when Port Richey Police Officer Donald Howard showed up to Massad's house, feigning a knee injury. Massad allegedly diagnosed Howard with an injured tendon, and was said to tell the undercover that he could obtain injectable medicine for the officer to administer on himself in the future.


When asked about this in jail, an unrepentant Massad suggested he was the victim of a conspiratorial plot by DeCanio and police underlings to get rid of him because he had advocated Port Richey voters dissolve the police department. But the main person backing up that claim is a former girlfriend.

"We've even got one person that has it on tape, with the chief saying… 'If he gets a felony, he can't be mayor,'" Massad said, suggesting cops had to concoct something to protect their own existence. "So they came up with practicing medicine without a license because I took some fish hook out of a guy’s back."

There is nothing in the public record to back up Massad's claim, and DeCanio dismissed the ex-mayor's allegation as fabrication. "Instead of taking responsibility for what he did, he wants to claim the police have a vendetta against him," DeCanio said. "Nothing could be further from the truth."

One might think being busted in a pre-dawn raid that got him slapped with attempted murder charges—of a SWAT team, no less—would rein in Massad's instincts. Instead, he was about to get himself in another pickle that brought even more negative attention to Port Richey.

Shortly before 11 PM on March 3, while stewing inside the Land O' Lakes jail, Massad placed a phone call to Terrence Rowe, the Port Richey councilman selected by the other three members to serve as interim mayor in the wake of his ouster. For several minutes, the small time politicos shot the breeze like old pals catching up on lost time. Then Massad shifted the conversation to Howard, the Port Richey cop who went to him for medical treatment.


"I believe Howard was hired illegally, fired legally, and rehired illegally," Massad said during the recorded call, according to an arrest report. "I don't know why, but he is in on everything."

Rowe replied, "You know, this doesn't go down without somebody answering for it!"

Eleven days later, Rowe was booked himself. At a bond hearing, prosecutors and Pinellas-Pasco Circuit Court Judge Mary Handsel concluded the acting mayor's comments implied he and Massad were going to tamper with a witness, in this case Officer Howard. Prosecutors tacked on felony counts of obstruction of justice and illegal use of a two-way communication device against the ex-mayor and charged Rowe with the same two counts. He, too, was suspended from office.

Rowe has pleaded not guilty, and his defense attorney did not return a phone message seeking comment. The five-member city council currently has two empty seats, but a special election for a new mayor was scheduled for June 18.

Meanwhile, Massad has made futile efforts to win his release. In April, the Florida 2nd District Court of Appeal quashed his lawyers' request to overturn Handsel's order that Massad remain incarcerated without bail. And Handsel denied his motion to disqualify her as the presiding judge, which argued she displayed bias against him and had a conflict of interest because she is married to a former cop.

As for the whole shooting at cops thing that got him into such massive trouble, according to an initial motion arguing for his release filed by his lawyers back in March, Massad armed himself so heavily because he believed he was about to be robbed and was in physical danger. The motion cited the history of dozens of 9-1-1 calls to Massad's home, including alleged burglaries, as proof that he had reason to protect himself. Massad's attorneys suggested that photographic evidence might prove he was firing warning shots and could not have hit anyone entering the home.

When interviewed, Massad held fast to his defense strategy. He said it was hard to hear people knocking on the front door of his house unless he was ten feet away from it. "I heard all this noise," he said. "I am groggy when I jumped out of bed and I am scared to death."

Mimicking how he was aiming his gun, Massad added that he fired warning shots that hit the wall of his elevator and an area directly in front of him. He insisted there was no way the bullets would have hit the officers coming through the front door.

On April 5, Massad's defense team gave reporters a crime scene tour of his house to make the same point. Using a laser pointer, his attorney, deVlaming, identified two spots on the second floor where the bullets struck. Based on where the bullets landed, the deputies were not in the line of fire, deVlaming told the assembled journalists. He also argued Massad feared home invaders masquerading as police were at their doorstep.

"From the 9-1-1 tape, you can tell both of them didn't know if these were real cops or fake cops," deVlaming said of Massad and Joseph, who called the police during the raid. "There have been plenty of times when fake cops have come to rip people off or do a home invasion burglary."

As of early June, Massad remained behind bars. He was set to go to trial on the obstruction and illegal communication charges later this month, but a trial date for the attempted murder and illegally practicing medicine counts—his original alleged crimes—had not yet been set. He also had a new bail hearing set for June 10.

At the county jail earlier this spring, a defiant Massad scoffed at the suggestion that he reflected poorly on his city. "It reflects on fucking America," he seethed. "I was mayor and they came in at 4:30 in the morning for no reason. They bust my door and they shoot into the wall, into my doors, they crack my door open… and I reflect on the city? Doesn't that bother you a little bit?"

Should he beat the charges, Massad could theoretically fight to get his job as mayor back. However, he seemed to have ruled out a return to Port Richey's city council. "I don’t ever want to be in politics ever again," he said. "I am a free spirit. This is killing me."

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