Jumping Into History: The Origins of Roman Trail

If Julius Caesar had paratroopers, the world would have looked very different.

That thought hit me somewhere above 10,000 feet during a freefall training jump with Special Forces. I had spent 13 years in the military, deployed 5 times, and had done everything from humanitarian aid to combat. I was ready for a new change, but what?

Daytime HALO jump from 25,000 ft with O2 mask

I’d been reading Roman military history between jumps—Caesar’s Legions by Stephen Dando-Collins—and started wondering how he’d have used modern rapid-insertion tactics. The man loved mobility, surprise, and overwhelming force. Cavalry charges were his version of airborne assaults, and he was always looking for new ways to flip a losing fight.

Back on the ground, my downtime wasn’t exactly ancient history—it was indie gaming on Steam, playing Oregon Trail, Organ Trail, and Death Road to Canada. The linear roguelike combination of crushing difficulty and dark humor had me hooked. Somewhere between reading about Roman legions dying of dysentery on PC, the idea collided in my head: what if players could try surviving the brutality of a Roman invasion in a game?

That was the moment Roman Trail was born.

When I left the military, I traded my combat gear for a laptop and sketchbook and jumped head-first (pun intended) into game design school. The discipline and structure of the military turned into game mechanics, concept art, and game documentation. The invasion of Britannia became the perfect setting—historical, linear, and packed with opportunity for parody. The legions’ relentless march north mirrored that familiar Trail-style gameplay loop: keep moving, make impossible choices, hope you don’t die horribly.

As an ex-army medic, I’ve always leaned toward dark humor—it’s how you cope with catastrophe. That tone seeped into Roman Trail’s DNA: a roguelike card game where every decision can save the day or doom the mule.

So begins the march.

This blog will follow the Legion’s progress—mechanics, art, playtests, and maybe a few glorious disasters along the way. If you’re into ancient history, pixel art, or watching developers slowly lose their minds, join our Discord and follow the Kickstarter pre-launch. Glory (and dysentery) await.