With its pink advertising wrapping, Winston's van gives the impression that the inside will have a party atmosphere. But it doesn't. The passengers, most of whom are from Jamaica (like Winston) or Trinidad, sit quietly. One Trinidadian woman dressed in business clothes overhears me interviewing Winston and volunteers that vans are a common way to get around the islands. The interior of the van is clean, gray, and institutional -- very much of a piece with Winston's overall business plan to brand his vans and make them mainstream.

He'd like to eventually move beyond the Flatbush route and pick up, say, hipsters in Williamsburg and bring them to Manhattan. If this sounds improbable, it's really not: Think of the incredible popularity of food trucks, which were known as "roach coaches" only 10 years ago. A hip fleet of dollar vans, providing proximity and cheap transit to 20-somethings, could easily catch on. If the vans ran on cleaner engines -- hybrids or natural gas -- they could be part of a greener city. (In another move to raise the profile of his vans beyond Flatbush, Winston allows a music promoter called Dollar Van Demos to film rappers in his vans for broadcast on the Internet.) But no broader growth can happen until the vans can be branded and made attractive to people who don't already know them, says Winston.

Ah, and that's where the illegality comes in. Winston used to have his vans all painted with a green stripe, so they became easily recognized in the neighborhood. While this "uniform" was good for business, his vans also caught the attention of police of various kinds who ticketed him for stopping to pick up passengers, and he accrued fines that ate into profits. This is the paradox of Winston's work: While he is fully licensed, insured, and inspected, his vans are prohibited from doing the one thing they really do -- picking up passengers off the street.

David King, from Columbia, quips that all dollar vans are 100 percent illegal (because they work the curbs), but some are 200 percent illegal (because they don't bother to get licensed in the first place). Winston says police don't cite the unlicensed vans, which eat into his business, but do go after the licensed ones for the curb infractions. "The law gets made up as you go along," Winston says, adding that the pink cellphone ad on the van is both an attempt to make a little money as he cruises up and down Flatbush, and a trial balloon to see whether there's a specific law prohibiting advertising on the vans. Later, one of the 500 or so completely illegal vans pulls up beside him, and in friendly Jamaican patois, Winston accuses the driver of being a terrorist. "It's not like I hate against them. But I'm running a business and they're running a hustle," he says.

The existence of laws and the lack of enforcement put the legal drivers in a bind that Winston describes as a Catch 22. In 1993, New York outlawed dollar vans entirely. It took the intervention of some activist van owners with the help of the Libertarian Institute For Justice to get them legalized. Deliberate or not, the city's perverse policy of half-legalizing legal vans and failing to enforce laws against the unlicensed ones limits the growth of what could be a useful transit resource. Winston describes a decade and half of Coyote and Roadrunner exploits with the law, concluding with, "Let there be a train strike, a blackout, a storm, or 9/11, and people are practically tearing the doors off." Last year, when the city was trying to cut bus routes, they even tried to substitute official dollar van routes, but that program was canceled when van drivers were uninterested in the routes, and riders were uninterested in the vans.