All the advantages, and nothing to show for it.

• Author: Hammond, Betsy
• Position: PORTLAND, OREGON

If any big-city school district should have a handle on its high school dropout problem, it would surely be Portland, Oregon.

Compact and bike friendly, this darling of urban planners draws middle-and upper-middle-income professionals to live inside its city limits. And they do something that their counterparts in Detroit or Washington, D.C., or Los Angeles rarely consider: they send their children to public schools. In a school district that enrolls 47,000 students, only 43 percent are poor (in Chicago, 85 percent are) and a majority are white (in Philadelphia, 13 percent are). White and middle-class teens are far less likely to drop out of high school than their minority and low-income peers.

But a shockingly low percentage of Portland's high school students graduate on time: just 53 percent. That puts its dropout rate on par with rates in Philadelphia, Louisville, and El Paso--all bigger districts with much higher concentrations of poverty. A majority of Portland's dropouts are white, only half qualify for subsidized school meals, and 90 percent are native English speakers.

It's not that Portland hasn't tried to do better. The school district has implemented a series of reforms, many of them strikingly similar to what New York City and Philadelphia, two cities with rising graduation rates, have been doing. A few of these reforms--turning to private outfits to run schools, upending the faculty and curriculum at schools with chronic low test scores, using sophisticated data systems to pinpoint instructional needs--are steps the Obama administration wants to encourage all school districts with achievement problems to adopt.

But in Portland, those reforms haven't worked. Despite fifteen years of effort, the city's dropout rate hasn't budged. How Portland took good ideas and managed to botch their implementation--through inattention and a failure to measure and demand results--is a cautionary tale for those in Washington who want to use federal dollars to get local schools to do right by their students.

Portland's first effort to grapple with its dropout problem began in the mid-1990s, when the school district vastly expanded what had been a small network of community-based alternative high schools. Founded in the 1970s and '80s, these privately run nonprofit programs had a good reputation around Portland for welcoming troubled teens who had dropped out of traditional high schools and reconnecting them to the classroom and society.

Expanding these schools seemed like a good way to benefit more of these vulnerable kids. But it also happened to benefit the Portland school district's bottom line. Voter-enacted changes in the way Oregon funds schools hit the Portland school district hard in the early 1990s. The surest and quickest way to refill its coffers was to lure back students who had dropped out.

It seemed like a win-win: disconnected students could find their niche in a nontraditional school setting, and the Portland school system could keep up to 20 percent of the state funds that paid for them to be there. Enrollment in the alternative programs doubled...