Daquiris and Doom - Rise and Fall of the Houseboat Mafia, Part 3

HEY YOU. YES YOU. This episode is part of a series. If you haven't yet heard the first 2 (or 2.5) parts of it, this episode won't make any sense to you.

In today's episode, we reach the conclusion of the Houseboat Mafia. How did the criminal empire react to the arrest of their beloved leader, Dockside Dick? How did the mighty syndicate go toe-to-toe with a gang of industrialist oligarchs? How did they fall so quickly?  Find out, only on Liminal Criminals.

(Actually those last two might be related now that I think about it. )

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CONTENT WARNING: Liminal Criminals is a fictional crime/comedy podcast, and contains elements which may not be suitable for all audiences. Listener discretion is advised.        

Transcript

Previously on Liminal Criminals: Ben and Mary Clarkson, fleeing from the debt they incurred through an animatronic fish scam, carved a swathe of violence on their voyage to the quiet, depressed settlement of Los Borrachos, Florida. There, they were drawn further into the criminal underworld after scheming with their new compatriot, Dockside Dick, and recruiting Cynthia Hawke, former trophy wife and perpetual drunken rage-beast. 

Through a combination of piracy, extortion, and smuggling, the newly formed Houseboat Mafia began to extend its reach throughout America’s “third coast.” But while they had reached new heights of material success, Dockside Dick and Cynthia Hawke still were not content with their position. Arguments about policy decisions, ethical dilemmas, and drink choices drove the gang to plan a series of daring heists to determine whose vision would shape the future of the syndicate. While preparing to spearhead an armored truck robbery, Dockside Dick was arrested, charged, and sentenced to life in prison. 

How did the other three leaders of the Houseboat Mafia respond to the arrest of their comrade? How did a powerful organization, still seemingly on its rise to dominance, collapse so quickly? We’ll answer these questions, and more, on today’s episode. 

I’m Sam Putnam. And you’re listening...to Liminal Criminals. 

[intro theme]

The leadership of the Houseboat Mafia did not bail Dockside Dick out of jail. While both Cynthia Hawke and the Clarksons wanted to help their friend make, and then skip out on, bail, several factors stood in their way. Firstly was the matter of money; as Dockside Dick was recognized both as a high-ranking member of an organized crime family, a criminal mastermind, and as a dangerous thug in his own right, his bail was set at ten million dollars. According to interviews with members of the Houseboat Mafia, Dockside was loath to have that amount of money be used in exchange for him having to live the rest of his life on the run. To make matters worse, the Houseboat Mafia was not accustomed to having large sums of liquid capital on-hand. Most of the syndicate’s cash was invested, either into money-laundering fronts, quasi-legitimate real estate deals, and jet-ski racing tracks. Even if Dockside wanted to walk free, raising the necessary funds would have been difficult, if not impossible. 

The weeks following Dockside Dick’s arrest were tense. The Houseboat Mafia’s illegitimate activities slowed to a crawl, the demoralized criminal empire not wanting to attract any further undue attention from the feds. Even Cynthia Hawke managed to control her volatile temper and need for stimulation, replacing her rashes of violent crime with regular “therapy” sessions where she beat the hell out of an underling who was, according to his colleagues, “into that sort of thing.” 

The brief lapse in the Houseboat Mafia’s reign over the Gulf brought its own host of problems. With the underworld branch of its enterprises hobbled, revenue slowed to a crawl. With the organization less inclined towards violence, rival gangs that were once brutally suppressed by the Houseboat Mafia began to regain their strength. Without a steady supply of drugs and guns, the gang’s footsoldiers were at a loss for what to do on their Tuesday evenings. A sense of quiet desperation saturated the air surrounding the criminal empire. 

As Dockside Dick’s trial dragged ever-onwards, Hawke and the Clarksons could see the writing on the wall. Dockside had refused a plea bargain, and the evidence against him was clear-cut. When word reached the Clarkson’s ears that the prosecution had produced photographic evidence of Dockside Dick dry-humping a mounted shark at the Florida State Fair, they knew that their friend had no hope of having a life outside of prison. By May 1st, 1992, the Houseboat Mafia began their next phase of evolution. 

Ben and Mary Clarkson came to the conclusion that if the Houseboat Mafia were to survive, then it could only do so with new alliances. They began to make their overtures to other power-players in the American criminal underworld, sending them bottles of high-end liquor, giving them gifts of premium narcotics, and offering them nights with escorts capable of performing a “Key West Slamjob,” a sex act on which I have been unable and unwilling to find information. 

These offers of allegiance were, by and large, accepted. The Houseboat Mafia, while reeling from the arrest of one of its leaders, was still seen as a valuable partner, owing in large part to its armada of stolen and cannibalized vessels, a lasting reminder of Dockside Dick’s legacy. Among the gang’s freshly-minted allies were the Cajun Separatist movement of Louisiana, the Trailer Park Titans of Alabama, and the Gator Fondlerz, with “fondlerz” being spelled with a “z,” of the Everglades. 

Over the ensuing months following Dockside’s conviction in July of 1992, the Houseboat Mafia focused primarily on the smuggling end of its operations. Using its well-oiled fleet and contacts throughout the criminal underworld of the Southeastern United States, they continued to run contraband to ports from Houston to Miami. The organization, admittedly, lost some territory. Whereas the Houseboat Mafia once controlled the goings-on in most small coastal towns along the Gulf, the bulk of its political power was now concentrated in the area surrounding Los Borrachos, as well as, allegedly, in the Twitchy Tuna, a popular seafood chain in the South. However, despite the blow that was dealt to its raw power in the criminal underworld, the Houseboat Mafia was operating more quietly, more efficiently, and with fewer casualties than it had in the past. 

This change was not universally well-received. Several of the Houseboat Mafia’s higher-ranking members grumbled that the organization had lost far too much power, and that the once-mighty syndicate had been reduced to a glorified courier service for the seedy underbelly of the Gulf. Chief among these malcontents was Cynthia Hawke. 

“Of fucking course I was fucking mad about that,” snapped Hawke at an interviewer following her arrest. “I didn’t leave my shitty old life to watch my friend get raked over the coals by the fucking pigs, only for me to be left high and dry to turn into some fucking errand girl for every scumbag from here to fucking Galveston! I fucking joined up with the fucking gang to pillage, plunder, and plow! I swear to fucking god, if I ever find the asshole who ratted out Dick, I’m going to [comically long bleep].”

As morale among the feistier members of the Houseboat Mafia suffered, tiny rifts in the organization began to emerge. A handful of the gang’s foot soldiers in Houston sold their boats and fled up north. The Clearwater chapter of the Houseboat Mafia got into a shootout with a gang of militant jetski enthusiasts. Cynthia Hawke went on an arson spree in Tampa, torching several homes, including that of Terry Knox, manager of a recently-rebuilt Garlic Pit. The Clarksons attempted to gain a handle of the situation, with little success. While the couple had managed to keep the gang’s financial and political affairs in order, they had lost many of their followers’ goodwill. They weren’t native to the gulf, but instead came from the suburban Midwest. They weren’t sanguine and outgoing, but instead were reserved and conniving. Ben Clarkson had recently developed an endocrine condition that made him reek of old sourdough bread, and that really wasn’t doing him any favors either. After the couple’s final attempt to win over Cynthia Hawke and the rowdier members of the gang, with an ill-advised celebration of “international thug appreciation day,” they realized that they would have to compromise. And so, they arranged a meeting with their fellow leader, and spoke the most horrifying seven words in Florida’s history: “Go ahead, Cynthia, do whatever you want.”

Cynthia Hawke did not immediately take this opportunity to wreak as much havoc as she conceivably could. Rather, she retreated to her cabin aboard the Good Riddance and began to plot. The inner circle of the Houseboat Mafia, who were canny enough to realize that nothing good could result from Cynthia Hawke keeping quiet and planning out her actions, spent the next few days in nervous silence as the crime boss placed calls, consulted schematics, and prepared, like a coiled snake ready to strike. 

When Cynthia Hawke finally called for a meeting with the upper echelons of the Houseboat Mafia, her plan was as simple and plainstated as it was suicidally-overconfident. 

In the middle of October, Florida’s Key Mammon would host the annual convocation of the Pleasance Trust for Better Patriots, a meeting of industry leaders from across the country. There, members would indulge in the finest pleasures offered by flesh, fermentation, and fine white powders as they forged their game plan for manipulating the strings of power in American politics. As far as Hawke’s contacts among the chattering classes of Florida could tell, the main meeting would be held at the Key Mammon Eden, a five-star hotel and convention center. The after-party would be held on a series of yachts, with glassware oligarch Melvin Pleasance’s prized ship, The Effluence, serving as the gala’s epicenter. During the late afternoon, however, the moguls’ ships would be empty, save for a skeleton crew of security staff. 

The Houseboat Mafia’s most decorated foot soldiers consisted of a combination of former Navy sailors, disgraced scuba instructors with permanent nitrogen narcosis, and comparatively well-socialized swamp mutants. With their combined expertise, they could swim up to their target vessels, undetected, plant explosive charges on their hulls, retreat to a safe distance, and detonate them, capsizing the unfortunate ships and forcing the crew to evacuate. 

The reaction to the plan was mixed. Its detractors, among them Mary Clarkson, noted that not only was the plan highly impractical and rife with the possibility for catastrophic failure, it would also attract the attention of the local authorities, the FBI, and, most dangerous of all, a series of vindictive billionaires who were denied the ability to snort piles of cocaine off of a California roll balanced on a sex-worker’s bared nipples. “I once heard that the PTBP made children fight to the death for their amusement at these things,” said Mary, “I didn’t want to think about what would happen if we got on their bad side.” 

Among the plan’s supporters were the bulk of Cynthia’s shock troops, as well as Ben Clarkson. Reasons for support ranged from a desire for the Houseboat Mafia to rear its head once more, to a revanchist urge against the society that had condemned their leader to a life in prison. “In all honesty, I didn’t see how it could go wrong,” said Ben. “If it worked, it would mean that we’d be walking away thousands or millions of dollars richer at the expense of some money-grubbing assholes. And if it went wrong, well, it wouldn’t have been us leading the charge, now would it? We had nothing to lose, and everything to gain.” 

In June of 1993, the plan was put to a vote among the members of the Houseboat Mafia, and passed with a slim majority; 52% believed that the plan should go forward. 46 percent did not. The remaining 2 percent was evenly split between write-in votes for Jimmy Buffet, Lynyrd Skynyrd, and Jesus, in descending order of popularity. 

The Houseboat Mafia operated, business as usual, for the next few months. When containers of precursor chemicals went missing from their shipments, the losses were chalked up to the contraband falling overboard on the trip across the Gulf. When the gang hired desperate engineers and chemists, none of the Florida underworld batted an eye; after all, gang labs were common. They didn’t suspect that their go-to drug-smugglers and gun-runners were planning to make themselves extraordinarily conspicuous. Even if they would have been opposed to the syndicate’s operations, they had no way of knowing what was going on among the drunken, debauched gang from Los Borrachos. 

Come October 10th, 1993, the Effluence, Melvin Pleasance’s proudest and most recent purchase, approached the marina off the coast of Key Mammon. Being too large to dock, it sent forth a smaller speedboat into harbor. Melvin Pleasance stepped off of it, the diamond-dust-infused threads of his sportcoat glistening in the morning light. The wind off the ocean failed to tousle his hair, each strand of which was locked into place by an experimental mousse which was technically illegal in the United States, Spain, Canada, Portugal, North Korea, South Korea, the Canary Islands and even Andorra. In his mind, nothing could possibly go wrong. 

As Melvin strode into the Eden, his coconspirators and their respective security details, followed. The garishly-dressed magnates and hulking men in bulging suits cut a swathe into the hotel, leaving behind a token number of security staff who simply weren’t intimidating, cool, or photogenic enough to accompany the movers and shakers of the world. Their ill gotten gains were now vulnerable to the Houseboat Mafia’s strike team. Clad in scuba gear with seabed-print camouflage, armed with explosive charges, and sober enough to be mad about it, the maritime marauders fell into the water a mile off the shore of Key Mammon, and began to swim towards their prize. 

It was then that Cynthia Hawke’s best-laid plans came into contact with the enemy.

The first problem faced by the cadre of ne’er-do-wells arose from the devices stored aboard the ships. The yachts belonging to Melvin Pleasance and company were equipped with the Poseidon Riptide, a security device which used proprietary technologies to create violent currents of water that would repel sealife and pirates alike away from the ship. 

“We were kinda flabbergasted about what to do,” said an interviewed member of Cynthia Hawke’s forces, who would only answer to the name “Gooch,” “But we eventually found that we had to get as close to the sea bed as possible until we felt the current let up. Once we got near the boat, the Riptide didn’t work quite so well. That was, y’know, assuming that we could even get near the boat in the first place.” 

Thus arose the second problem in Cynthia Hawke’s plan to loot the ships of the PTBP. It’s difficult to say why the security team had taken to randomly firing automatic weapons into the turbulent water none of them had seen the approaching strike team. Perhaps it was out of boredom. Perhaps it was an unmentioned aspect of the PTBP’s security measures. Perhaps they were indulging in that most American of all pastimes: gun-fishing. Regardless of the reason, however, this new complication meant that the Houseboat Mafia’s forces had to approach the boat under wild, intermittent hails of gunfire. While none of the bullets managed to severely injure or kill the approaching bandits, a few lucky shots managed to wing their targets. 

“I was just about to reach the boat when one of those fuckers managed to graze my ass with a bullet,” said Gooch, “Now, I’ve puked enough blood into the ocean to know that I didn’t need to worry about sharks or anything like that, but I also knew that ‘underwater’ is one of the last places that you want to have a second asshole bleeding like mad. We had to operate quickly.” 

Pressed for time, the members of the Houseboat Mafia planted their charges to the hull of the ship and got out of Dodge. When everyone had retreated to a safe distance, an accomplice on shore pressed the first detonator. 

The explosions from the Effluence rocked the waters off of Key Mammon, sending a shockwave of panic through the witnesses on shore. As the vessel sank into the Atlantic, speculation arose among the crowd. Most bystanders agreed that it must have been an accident or mechanical fault aboard the yacht. As the evacuating security personnel reached land, and as the Houseboat Mafia’s team of looters boarded the ship, waterproof duffelbags in hand, the crowd began to calm down. 

It was then that Cynthia Hawke’s lieutenant pressed the second detonator. 

The vessels belonging to Melvin Pleasance’s compatriots exploded like eggs in a microwave, sending the crowd fleeing in terror. A series of secondary charges planted on the bridge to Key Mammon went off at the same time, sending the structure crumbling into the hungry ocean below. With the sole entrance to the island blocked off, the Miami PD’s response was slowed; only a handful of cops on Key Mammon were able to respond, and they were too preoccupied with ensuring the well-being of the PTBP to keep an eye on the capsized vessels. 

In the eight minutes that it took for the Miami PD to mobilize a maritime patrol to the island, the Houseboat Mafia was able to strip the sunken ships, claiming nearly ninety million dollars in valuables, including artwork, precious metals, and antique pens. It was, in short, one of the biggest heists of the 20th century. 

Regrettably for the Houseboat Mafia, Mary Clarkson’s concerns about angering the captains of American industry were well-founded. Now that the Houseboat Mafia had struck somebody that the United States government actually cared about, the FBI’s investigation into the Houseboat Mafia began in earnest. Cynthia Hawke was arrested in February of 1994 on charges ranging from arson to domestic terrorism. Given the lack of subtlety in her heist, her criminal career, and her life in general, she was convicted in December of the same year. 

Dozens of members of the Houseboat Mafia were arrested in the subsequent months. In Galveston, a safehouse was raided and three of Hawke’s lieutenants were arrested. In Los Borrachos, the homes of several high-ranking members of the Houseboat Mafia, including Daquiri Dan, Gooch, and The One Known As Chhhurk, were brought in for questioning. In Shrimp Huffer Florida, an illegal betting parlor run by the syndicate was surrounded. The crab-fighting ring inside began to fire at the authorities, leading to a deadly SWAT raid. Throughout the Gulf, the Keys, and the eastern coast of Florida, the Houseboat Mafia crumbled.

The Clarksons went to ground. They managed to live in hiding for another year aboard the Clean Getaway, living off of the cash they could salvage before the feds came knocking. They were eventually captured in May of 1995, when a customer at the Twitchy Tuna in Pensacola recognized them from a recent episode of Get Those Sumbbiches, a local show modeled off of America’s Most Wanted. 

Ben Clarkson, Mary Clarkson, Cynthia Hakwe, and Richard Dox, known to his friends as Dockside Dick, had been arrested. Their criminal empire lay in tatters. The Houseboat Mafia had crumbled, leaving naught but ashes and the faint odor of chum in its wake. 

What has happened since then? 

Los Borachos’ tenure as a money laundering hub for the Houseboat Mafia gave it the injections of cash it needed to construct actual infrastructure and become a proper town. It was incorporated in September of 1994. Today, it is most notable for being the home of ParrotCon, a convention for afficionados of Gulf and Western music, as well as people who enjoy dressing up as tropical birds. 

Gooch and Daquiri Dan accepted a plea bargain at their trials, and were released in 2010. They currently run “Gooch’s,” a bar in Tallahassee, as well as “Danny and the Gooch,” a shock-jock styled comedy podcast which has been described by critics as “Technically listenable.” 

Derek Owens graduated college in 1993 with a “probationary Bachelor’s degree” in communications. He currently runs EarthLover, a multilevel marketing company selling nutritional soils which cannot be marketed as a foodstuff, a medicine, a supplement, or a gardening supply. 

Cynthia Hawke was imprisoned in the Sandbar County Correctional Facility for Women after her conviction. In 2001, after several years of running a gang of former Houseboat Mafia members and conducting interviews with the media whenever possible, she was shanked in the gut by a rival gang member. Cynthia Hawke died of her injuries but not before tackling her assailant to the ground and ripping out her throat with her teeth. She was 43. 

Ben and Mary Clarkson accepted a plea bargain and were sentenced to 30 years in minimum-security prison. While they are slated to get released on good behavior later this year, it is unlikely that they will live to enjoy much of it, as both have been reported to be suffering a rare form of thyroid cancer. Foul play is not officially suspected. 

Ava Clarkson, following a scandal-rocked career as a mechanical engineer, left Missouri in 1998 and moved to Shreveport, Louisiana. She met a fellow engineer, Armando Armand, and the two were wed in 2000. They had a daughter, Mary, one year later. 

Mary Clarkson-Armand, while academically successful, had a troubled childhood, incurring multiple suspensions for her enterprising and often-violent behavior. In 2019, one month into her first year at Louisiana State University, she went missing. 

The few members of the Houseboat Mafia who weren’t arrested were left in disarray. Most abandoned their life of crime, taking up jobs at local marinas or fisheries. Some joined other gangs, or started their own with the resources they had left. Regardless, it would be safe to say that the Houseboat Mafia is well and truly dead. 

But in the past year, there have been a rash of robberies at sea. The few lucky survivors of these attacks have reported a crazed young woman in a speedboat boarding their craft and beating them senseless with a singing animatronic fish. A luckier few have heard her name and seen her craft. 

So let me end this podcast a plea. If anybody has seen a speedboat called the “Clean Getaway,” or a wild-eyed woman in her 20s calling herself “Margarita Mary,” please contact the local authorities. 

This has been Liminal Criminals. I’m Sam Putnam. I’ll see you next time, and remember: Regret will stay their hand. 

[ending theme] 

Liminal Criminals was originally a true crime podcast by Liminal Studios. It was originally researched, written and created by Sam Putnam. It is edited for broadcast and distribution with the generous support of the Chthonic Riviera government and Deeps Self-Preservation League. Up next, I’ll be bringing you the news with the evening edition of Studio Community Worldwide Radio. 

Also, Krysta, if you’re listening, holy shit, do you that the Margarita Mary from before is the same one that runs that caravan now? Do you think we could get an interview with her? 

Liminal Criminals is a fictional podcast by SCWR productions. It is written and edited by Sam Putnam. It is cowritten by Krysta Golden. Our theme song is Chthonic Riviera by Cornu Ammonis. 

Folow us on Twitter at “liminal cast,” or like us on Facebook. Rate and review us on iTunes, Spotify, or your podcast platform of choice. Tell a friend about us. Look up at the sky and know what’s coming. All links are in the show notes