“Don’t Go Out Sad: The High-Top Hustler of DC”

 “Don’t Go Out Sad: The High-Top Hustler of DC”

(A satirical short story in the spirit of Turtledove meets Chappelle, but no one gets roasted too hard.)

---

It was a brisk October morning in Washington, D.C., the kind where politicians wear Patagonia to pretend they’re regular folks and interns drink oat-milk lattes to forget they owe $200k in student loans. But one man wasn’t concerned with either Patagonia nor politics. No — he was focused on soles.

His name? Don’t Go Out Sad. That’s not a motto. That’s his actual, legally changed name. (Formerly Darrell Quinton DeVaughn III, but that was before he got enlightened in a Denny’s parking lot after watching a National Guard TikTok.)

Don’t Go Out Sad — or "Sad" to his friends, ironically — ran a wildly successful high-top sneaker business out of a converted food truck parked permanently two blocks from the Capitol. His brand? Guard Kicks™. His clientele? Everyone from National Guardsmen in full camo to aides from both sides of the aisle who had been waitlisted for 14 months just to get a custom sketch of Teddy Roosevelt doing CrossFit on the side of a Jordan 1.

Each pair was hand-painted. Each came with a little scroll of handwritten motivation quotes ("If you're gonna filibuster, at least flex while you do it.") and, most famously, a little satchel of mint Tic Tacs — a brand choice he made solely because "the man makes a mint off these kicks."

---

The Hype was real.

Cable news anchors wore them under the desk. Congressional staffers formed sneaker caucuses. At one point, even Senator Kyle Mathers of Nebraska — a man whose campaign slogan was “Corn over Cool” — showed up in a pair of Guard Kicks featuring an eagle surfing on a tank. The Internet exploded. Sad’s phone melted. His business did numbers.

But his proudest customers? The National Guard.

Sad was their unofficial hype man. Whenever the Guard got called in — for protests, parades, or that time someone tried to break into the Library of Congress to prove it was fake — Sad was there, handing out fresh pairs like Oprah with custom laces that read “SECURE THE SWAG.”

---

His rise was meteoric. By fall 2025, Don’t Go Out Sad had sneaker collabs with the Smithsonian, three documentaries in production, and a modest mansion in the Navy Yard shaped like a boot.

But the moment of reckoning came when President Kelvin Marsh — America’s first president to post his own memes — tweeted:

“If Don’t Go Out Sad isn’t designing my inauguration kicks, I’m not showing up.”

That’s when Sad knew he had made it.

He pulled an all-nighter painting a pair of presidential Air Force Ones with fireworks, founding fathers doing backflips, and the phrase “Unity in the Streets, Heat on the Feet” stitched in gold thread.

---

The big day came. The nation watched as the president walked onto the stage, camera zooming in on the custom sneakers. A tear rolled down Sad’s face. Even C-SPAN got a little spicy with the camera angles.

But just as the president leaned over to whisper, “These are fire,” Sad felt a strange shift in the air — like gravity hiccupped.

Everything slowed.

The crowd faded. The sounds of cheers dissolved into the soft hum of a Samsung Galaxy ringtone.

Sad blinked.

---

He was no longer on the National Mall.

He was on the Metro, dead asleep, cheek pressed against the window, mouth slightly open. A crusty Tic Tac had fused itself to his hoodie.

His canvas bag of sample high-tops sat at his feet, untouched. His sketchbook lay open to a half-finished doodle of a tank in sunglasses. His name tag from Foot Locker, still clipped to his chest, read “Darrell.”

Above him, an ad for the National Guard read:
"Serve with Pride. Step with Purpose."

He rubbed his eyes, chuckled to himself, and muttered:

“...I gotta trademark Guard Kicks before someone else does.”

Then the train pulled into Gallery Place, and he stepped off — maybe not famous, maybe not rich — but definitely not going out sad.

---

THE END
(…or the beginning?)

---