Episode 21: Rudy’s Caribbean Side Hustle

Just when we thought the Transitionarium had reached peak absurdity, Rudy Giuliani sauntered back into the building looking like a lost extra from a Jimmy Buffett concert.

He sported a Caribbean tan that verged on orange, beads of sweat perched on his forehead, and an outfit so rumpled that he could have been mistaken for a wayward beachcomber.

The smell of coconut sunscreen and cheap rum trailed him through the halls.

Part 1: A Sweaty Surprise

Staffers paused, mid-coffee sip, as Giuliani entered, half-mumbling some story about a “boozy ferry” and “hidden treasure maps.” Trump glanced up from his latest “Winning Executive Orders” binder, eyes narrowing at the sight of his former confidant.
“Rudy, you look terrible,” Trump remarked, half-amused, half-disgusted.

Rudy wiped his brow. “Long story, boss,” he panted, loosening what used to be a tie but now looked like a rag. “Let’s just say the Caribbean sun is less forgiving than the New York courts.”

Part 2: The Shocking Discovery

While Rudy’s return alone would have rattled our nerves, I soon stumbled upon something even more unnerving. In the quiet corner of the Deciderium, I found his laptop—propped up beside a half-empty piña colada glass (complete with tiny umbrella). On the screen was a website emblazoned with gaudy banners:
“Vote Giuliani!”

And right below, rows upon rows of familiar products: Trump watches, Trump guitars, and—oh no—Trump Bibles. Except Trump’s name had been crudely crossed out on every single item, replaced by “Vote Giuliani” in a neon font that could induce migraines.

Part 3: Brand Betrayal

My jaw dropped. Hundreds of items that we’d recently tried to offload as diplomatic gifts or clearance merchandise now populated Rudy’s makeshift marketplace. Instead of “Trump Time is the Best Time,” the watches now read “Make Time for Giuliani.” The guitars, once promising “Strumming for Greatness,” now touted “Strum for Rudy’s Revolution.” And the Bibles? Don’t even ask. Let’s just say rewriting holy text to plug a personal campaign might be a new low.

Jared Kushner, peering over my shoulder, choked on his bottled water. Kellyanne gasped, a sound like a deflating balloon. Eric whispered, “Dad’s not gonna like this…”

Part 4: Trump’s Reaction

As I confronted Rudy with the evidence, Trump was already storming toward us, tie fluttering like an angry flag. “Rudy!” he thundered, finger jabbing toward the laptop screen. “What is this… this sabotage?! I gave you watches, Bibles—well, they were mine originally—and you go and rebrand them for your campaign?! There’s not even a campaign! Is there?”

Rudy attempted a charming grin. “Boss, I figured I could help raise funds… for a future run. Y’know, just in case we needed… backup.”

Trump’s face went through several emotional contortions—disbelief, rage, mild admiration for the hustle, then rage again. “Giuliani, you street vendor wannabe, get these monstrosities offline immediately!”

Part 5: Sweating in the Spotlight

Rudy, still dripping sweat, fumbled with the keyboard. Each click seemed to send another cheesy “Vote Giuliani!” banner flashing across the screen. He mumbled apologies, promising full refunds and vowing to restore Trump’s good name in all product listings.

Kellyanne was already crafting a press spin: “We’ll say it was a rogue marketing intern. Or a Russian hack. Or maybe we just deny it ever happened. Yes, that might be simpler.”

Part 6: Coming Attractions

As Rudy scrambled to salvage his second-hand branding fiasco, Trump looked on with a mix of exasperation and reluctant amusement. One thing is certain: Giuliani’s Caribbean escapade left him sunburned, sweaty, and out of Trump’s good graces—again.

The staff now wonders what fresh chaos tomorrow will bring.

Will Rudy face a merciless rebranding trial?

Will Melania’s secret perfume experiments factor in?

For now, we’re stuck with piles of mislabeled merchandise and a crashed website that screams “Vote Giuliani” in neon letters to a world that probably never asked for this pitch in the first place.

Yours in confusion and counterfeit campaigns,
Brand Betrayal Investigator and Rogue Merch Tracker