Dwain Northey (Gen X)

My Dearest Caroline,

I write to you from the battlefront of the Great Chicago Conflict of 2025, where our gallant National Guard regiments—those brave defenders of Freedom and Frappuccinos—are locked in mortal combat with the most fearsome enemy this Republic has ever known: teenagers with iPhones and oat milk lattes.

Oh, Caroline, you cannot imagine the horror. The enemy lines stretch from Wicker Park to Lincoln Square. Their banners are rainbow flags; their muskets, reusable metal straws. They advance not with bayonets, but with hashtags and carefully worded social justice slogans. Our men, untrained in this new form of warfare, have been forced to adapt—some by attempting to confiscate TikToks, others by simply crying into their protein shakes.

General Biff of the 32nd Tactical Pickup Truck Division sent word this morning: “We have secured the Starbucks on Clark Street. Casualties were heavy—three soldiers mistook the Pumpkin Spice Latte machine for an IED.” A tragedy, to be sure.

The city is in chaos, Caroline. At night, the wails of sirens mix with the dreadful rhythm of bass from rooftop parties. The streets run red with spilled IPA. Brave Corporal Kyle attempted to arrest a man for “loitering with intent to craft beer,” but was swiftly overwhelmed by a battalion of hipsters quoting city ordinances at him. He was last seen being forced to try kombucha.

Meanwhile, in the southern districts, our supply chain falters. The men are rationed to one Chipotle burrito per day. Some whisper mutiny. Sergeant Chad declared, “We didn’t sign up to fight our own people—we signed up to look tough on Instagram!” Oh, Caroline, his words ring true. The war has changed them all.

In the western front—known locally as Los Angeles—our reinforcements report terrible confusion. The troops mistook a film shoot for an insurrection and occupied a movie set for three days before realizing they had merely joined the cast. The footage, I’m told, will be released on Netflix under the title Freedom Patrol: Based on a True Delusion.

But perhaps the fiercest battles rage in Portland, where the 14th Tactical Flannel Brigade made their last stand against the anarchists of Brewpub Battalion. They fought valiantly, even after realizing most of the enemy were baristas just asking them to recycle properly.

The toll is great, Caroline. Not in lives, but in dignity. For how can one measure the loss of reason, the surrender of logic, the sheer idiocy of sending uniformed troops to liberate Americans from their own coffee shops?

Still, our leaders declare victory. They claim the streets are safe, though no one asked them to make war in the first place. And so, as I write this by candlelight in a commandeered Whole Foods, I can only pray that one day, historians will look upon this foolish campaign and say: Here ended the dumbest war ever fought on American soil.

Until then, my dearest Caroline, I remain your devoted soldier,

Private First Class Todd “Freedom” Jenkins

32nd Selfie Infantry

P.S. Tell mother I love her, and tell the government to please stop deploying us to cities that have brunch reservations.