IT'S 4:30 AM and we still have 200 papers to deliver and my bike wheel is on fire.

I got a flat while trying to jump off a curb in pursuit of Preston Freeman, one of the city's last bicycle-bound paperboys.

Freeman spends every dawn circling Northeast Portland with two giant baskets full of Oregonians—but banish any thoughts of a 12-year-old on a Schwinn Sting-Ray. Freeman is a 42-year-old on a sturdy mountain bike and, with the flair of a guy who spent years as a bike messenger, rips the flat tire off my wheel before I can do it myself.

"Want to see a trick my grandpa taught me?" he says. He spreads the patch adhesive on the rubber and whips out a lighter. All of a sudden, where there was once a hole, there is now a small field of flame. The flat is fixed in no time, and Freeman's back to slinging papers on porches and ranting about the future of media.

For five years, Freeman has spent dark morning hours riding around the city by himself, throwing paper after paper to neighbors who are still asleep. Mondays are rough because the paper is so light, it's tough to throw correctly. Sunday's papers feel like cinderblocks. Today is Monday, and Freeman is an excellent shot, hitting almost every single porch on the first try, flipping the paper like a Frisbee while he rides with one hand.

"It's like messenger retirement," says Freeman who, unlike many drivers, doesn't hold a second job. The $50 a night or so that he scores from the paper route keeps him afloat, as long as he lives on the cheap. But Freeman is one of a nearly extinct species. If the ease and comfort of delivering via cozy sedans doesn't get him, the Death of Print Media will.

"Why get yesterday's news tomorrow?" he jokes. He gives the paper three years, tops.

The Newspaper Association of America estimates that 81 percent of newspaper delivery people are adults who sling their papers from cars. Delivering Portland's only daily involves bagging the papers at 2:30 am and getting them all on stoops by 5:30 am, all for only 10 to 20 cents a paper. Freeman knows only one other person who does the gig by bike.

All of the long, quiet mornings give Freeman a lot of time to think, and this morning he's a fast talker, bubbling over with ideas, excited to have some company. We run through the album he'd want if trapped on a desert island (The Clash's London Calling), his dietary beliefs ("don't eat anything with eyes"), his scheme for attaching video cameras to the helmets of bike messengers, and his failed business delivering weed by bike.

We loop back and forth through the silent streets. Freeman doesn't use a map or need a list of addresses. Every once in a while, he scorns having to throw a "sample paper"—about 25 of his 275 papers are to people who don't subscribe to the O, but whom paper execs hope they can catch with a free trial.

Sunrise is still far from the horizon when we finish the route. Despite his grim outlook for the future of media, Freeman isn't quitting any time soon. He loves the job, loves the traffic-free rides, loves the silent time to dream.