Skip to content

Jeff Cassman

Between Opportunities

Menu
  • Home
  • About Jeff
  • Books
  • Contact Jeff
Menu

The Pirate of the Cumberland

Posted on July 6, 2025July 12, 2025 by Jeff Cassman

It was a fine July morning on OHL—humid, sunlit, and vibrating with reckless optimism.

Mark rolled into the Cherokee marina parking lot like a man with a plan and zero understanding of physics. He emerged from his 2003 Suburban (which he had christened The Kraken) wearing aviator sunglasses, board shorts, and an unbuttoned Hawaiian shirt that screamed divorced magician energy. Draped over his shoulder was a pool noodle he referred to as his “first mate.”

He strolled up to the rental kiosk with the swagger of a man who thought liability waivers were merely suggestions.

“I be the Pirate of the Cumberland,” he announced to the teenager behind the counter. “And I’ll be taking Pontoon 14 off yer hands.”

The teenager blinked once, then twice, unsure if this was cosplay or a mental health emergency.

“Uh… okay. Ten people max. No towing. No excessive noise. And absolutely no renaming the vessel—company policy.”

Mark slapped down his ID and a laminated certificate titled Official Renaming Ceremony for S.S. Wet Dreams.

“She sails under new colors, lad.”

By noon, the pontoon was a floating estrogen bomb. Thirteen bridesmaids—yes, thirteen, not counting Mark—wearing matching neon-pink swimsuits emblazoned with “Bride’s Babes” had boarded the now-rebranded S.S. Wet Dreams. They came armed with Bluetooth speakers, vodka in Capri Sun bags, seven coolers, a charcuterie board shaped like a penis, a fog machine (for reasons), and at least one vape pen that doubled as a highlighter.

Mark was the only man onboard, but he stood at the helm like Captain Ahab on a bachelorette-themed whaling expedition.

The pontoon was rated for 10 people. Ten sober people. Instead, it carried Mark, thirteen barely balanced human margaritas, and enough booze to embalm a Clydesdale.

The lake was smooth. The vibes were impeccable. White Claws fizzed. Music thumped. Mark screamed nautical nonsense like:

“TO MARGARITAVILLE, LASSIES!”

It was all going so well. Until, of course, the wake.

They never saw it coming. A wake—no, a beast—created by a wakeboarding boat named Boaty McYachtface, captained by a shirtless frat goblin named Gunner and his buddies crushing beers mid-backflip. The wave rolled toward them, high and lurching, like Poseidon had finally noticed Mark was playing pirate and wanted to intervene.

Mark could have slowed down. Could have turned gently.

He did neither.

“Head on!” he bellowed, raising a plastic cutlass. “We show no fear!”

The bow met the wave with a sickening slap. The boat surged skyward—then nose-dived like a depressed dolphin. Water exploded over the deck. The bridal party screamed.

Phones flew. Purses floated past like abandoned dreams. A Kate Spade bag vanished beneath the surface in a sad little gulp. Hair, once curled with loving precision, now clung to foreheads in soggy tendrils. False lashes fluttered off faces like butterflies escaping a burning salon. The pink inflatable flamingo let out what sounded like a whimper as it somersaulted into the abyss.

Mark, panicked and clearly guided by a cocktail of adrenaline and Tito’s, threw the throttle into reverse.

This was not ideal.

Instead of correcting the situation, it deepened it. The rear end of the boat lifted. The nose sank further. It was as if the S.S. Wet Dreams wanted to become a submarine.

A cooler launched into the air. Brie and strawberries scattered like confetti at a funeral. The Bluetooth speaker sparked and fizzled, playing the first six bars of “WAP” before dying with a gurgle.

Then, the gas leak.

The impact had jostled a fuel line, and now a shimmering rainbow slick spread across the water’s surface. The boat was half-submerged. The bridesmaids were scattered. One girl screamed, “This was supposed to be MY DAY,” even though it absolutely was not.

Another sobbed, “My backup lashes were in my purse!”

Towels hung like wet flags of surrender. The guacamole had vanished. The fog machine was bubbling ominously. Mark stood soaked, sword still raised, sunglasses crooked, one shoe gone.

He surveyed the damage and whispered:
“She held the line, boys. She held…”

They were rescued by Dusty, a local legend in a tank top that said Lake Hair, Don’t Care. He arrived on a camo Jet Ski trailing the smell of Axe body spray and watermelon vape, looked over the wreck, and said:

“WTF. Did y’all hit a log?”

Back at the dock, the marina manager watched the soggy procession limp ashore and sighed.

“Pontoon 14,” he muttered. “Again.”

Mark was fined. Threatened with legal action. Banned indefinitely.

And yet—invited to the wedding. Tiffani thought it was hilarious.

“That’s just Mark,” she shrugged. “He’s like…a legend.”

To this day, people speak of The Pirate of the Cumberland. Of the Bridesmaid Mutiny. Of the cursed voyage of the Wet Dreams.

And Mark?
Mark still insists he had it all under control.

“Look,” he says, with a drink in hand. “Nobody died. Nobody drowned. And if anything, I brought us all closer together. Also… that flamingo float might still be out there.”

He pauses. Sips. Nods.
“Sailin’.”

Search

Categories

  • Abortion
  • AI
  • Aquaponics
  • Art
  • Autism
  • Business
  • Churchy Stuff
  • Cooking
  • Cool Stuff
  • Culture
  • Economics
  • Education
  • Election
  • Family
  • Fitness
  • Government
  • Health
  • History
  • Holidays
  • Homeschooling
  • Humor
  • Immigration
  • Justice
  • Keto
  • Kids
  • Law
  • Marketing
  • Marriage
  • Men
  • Misc
  • Music
  • Musings
  • Old Hickory Lake
  • Parenting
  • Poetry
  • Politics
  • Prayer
  • Prison
  • Protestants
  • Sedevacantism
  • Singing
  • Statistics
  • The Wuhan Pandemic
  • TSA
  • Uncategorized
  • War
  • Women
  • Worthy Causes

Archives

  • July 2025
  • April 2025
  • March 2025
  • February 2025
  • August 2024
  • July 2024
  • June 2024
  • April 2024
  • March 2024
  • February 2024
  • November 2023
  • October 2023
  • September 2023
  • August 2023
  • July 2023
  • June 2023
  • May 2023
  • April 2023
  • February 2023
  • January 2023
  • December 2022
  • February 2022
  • January 2022
  • December 2021
  • November 2021
  • September 2021
  • August 2021
  • July 2021
  • June 2021
  • May 2021
  • April 2021
  • March 2021
  • February 2021
  • January 2021
  • December 2020
  • November 2020
  • October 2020
  • September 2020
  • July 2020
  • June 2020
  • May 2020
  • April 2020
  • March 2020
  • January 2020
  • December 2019
  • November 2019
  • October 2019
  • September 2019
  • August 2019
  • July 2019
  • June 2019
  • May 2019
  • April 2019
  • March 2019
  • February 2019
  • January 2019
  • December 2018
  • November 2018
  • October 2018
  • September 2018
  • August 2018
  • July 2018
  • June 2018
  • May 2018
  • April 2018
  • March 2018
  • February 2018
  • January 2018
  • December 2017
  • November 2017
  • October 2017
  • September 2017
  • July 2017
  • June 2017
  • May 2017
  • March 2017
  • February 2017
  • January 2017
  • November 2016
  • October 2016
  • September 2016
  • August 2016
  • July 2016
  • June 2016
  • May 2016
  • March 2016
  • February 2016
  • January 2016
  • December 2014
  • November 2014
  • October 2014
  • September 2014
  • August 2014
  • July 2014
  • June 2014
  • May 2014
  • April 2014
© 2025 Jeff Cassman | Powered by Superbs Personal Blog theme