Cigarettes, rotting orange peels and trash litter the ground. The broken windows in the nearby buildings recall meth addicts' dentistry. This is Portland's skateboard heaven.

In 1990, a bunch of Portland skatepunks occupied the eastern underbelly of the Burnside Bridge. They evicted the bums and hookers, and built a concrete moonscape: steep slopes and round-bottomed basins, designed to aid in the defiance of gravity. After wooing the neighbors and cops—"we kissed a lot of ass," one founder recalls—the squatters won City Council's blessing in 1992. (Even now, no one's sure who legally owns the land.)

Today, the Burnside Skatepark is a global Mecca for the four-wheeled set. Video games immortalize it. An extreme-sports tour sponsored by NBC plans a championship event there this June. And now, this grimy outpost is a critical front in one of Portland's biggest real-estate battles, a development deal that will redefine the city's east side.

The Burnside Bridgehead project—expected to take at least three years and cost up to $250 million—will transform five blocks just north of the bridge into retail space, offices and apartments. Three rival developers are fighting over the fat contract to build the project. The winner will be anointed in April by the Portland Development Commission, which is holding a public hearing on the project tonight.

The Bridgehead made headlines this winter, after public outcry forced two contestants to drop plans for a Home Depot-style "big box" store on the site. Now the rivals are scrambling to embrace the inner east side's distinctive grit. All three proposals feature skatepark improvements, including spectator facilities, expansion of the compact park to the north and better access.

"There's a sophisticated edginess to the park," says Kevin Johnson, an architect with Gerding/Edlen, one of the three rivals, which has won many contracts from the PDC in the past. "They were given an opportunity to legitimize themselves, and did it. If we have the chance, we need to build something that enhances it."

The paradox is delicious: A big-bucks mega-project will end up wedded to the skatepark, child of anarchy, while well-heeled developers fall over each other to prove their street cred.

"We're from a universe a lot closer to the skatepark than the other two," says Brad Malsin of upstart Beam Development, the smallest competing firm and the one that shunned the big-box concept from the beginning. "I think they're about 12 light years away." (Malsin's team, according to Burnsiders, reached out to the park first. The other two rivals have followed suit.)

Rather than fight the invasion of their domain, Burnside's native tribe seems to welcome it.

"Our park is different than any other park in the world," says Chuck Willis, a 34-year-old Burnside founder. "We want to keep the attitude and the mystique. But whoever gets the project, we want to be on the right foot with them. This will change Burnside, but it could also do really good things for the park. We want to make sure that happens."

PDC will hear public comment on the Burnside Bridgehead project from 3 to 5 pm Wednesday, Feb. 9, at 222 NW 5th Ave.