IMAGE: Mike Wilkes

After the company narrowed the national search to five candidates, Superintendent Vicki Phillips selected Leon Dudley from Dallas. She called him "a dynamic leader who has proven his success at urban schools much like Jefferson."

Last week, in the latest blotch on Dudley's troubled tenure and on Phillips' eventual legacy, district officials announced Dudley is on leave and a new administrator will run Jeff for the rest of the school year.

So, was Dudley the best candidate? The Oregonian's editorial board wrote on Friday, April 13, that the national applicant pool had been "shallow indeed." But documents obtained by WW tell a different story about the four finalists whom Dudley beat out to head the North Portland school, where top-level administrators seem to come and go faster than rain showers in April.

Given the qualifications of at least two other finalists—Steve D. Wilson and Irby L. Miller—Dudley was far from the obvious choice. And, given that the search firm failed to uncover several warning signs in Dudley's past, the $33,000 it got also appears questionable.

"I don't think there was a clear indication Dudley was head and shoulders above the other candidates," Martín González of the Portland Schools Alliance said after WW showed him the résumés. "I would say Steve Wilson had an advantage...based on his experience."

The four other finalists included:

Wilson, [résumé] a longtime Washington teacher and administrator, and the only finalist who wasn't African-American.

Miller, [résumé] an administrator with the Baltimore school district for 20 years.

Rosiland Seavers-Swain, [résumé] an assistant principal at a middle school in Peoria, Ill., since 2005.

Michael Jackson, [résumé] who'd headed a group of charter schools in Washington, D.C., from 2003 to 2005.

"I really thought I had the experience and the knowledge to be a good fit," says Wilson, who is white. "The race issue never came into play—I didn't think."

Exasperated Jefferson supporters are now wondering why Phillips hired Dudley and what the district will do to stabilize a campus with a dwindling student population and a precarious reserve of goodwill.

Jefferson—Portland's only majority-black high school—has long been an epicenter of debate; the city's fault lines of race, class and power intersect there. But Dudley created new friction. Students complained about his rules and empty promises. Teachers took issue with his style. "I got the feeling he thought nothing positive had ever happened at that building prior to him," says Brian Quinn, a guidance counselor at Jefferson.

Parents also questioned his spotty résumé and his troubled work history, especially at one middle school with Salem-Keizer Public Schools. According to news reports and interviews with teachers there, Dudley spent one year in Salem before abruptly resigning. Teachers had bridled under his leadership, and the pattern appears to have been repeated in Portland. News reports from Dallas also raised questions about his use of district-issued credit cards and grant money.

Like all new principal hires in the Portland school district, Dudley got a one-year probationary contract. But Dudley's sudden departure casts doubt on the possibility of a contract renewal. At $120,000 a year, Dudley's salary was the highest among Portland's nearly 90 principals.

Phillips says Dudley will be evaluated just like any other probationary employee, when and if he returns from his leave. Given the uncertainty and the district's $620,000 payout to fired human-resources director Steve Goldschmidt, School Board members are cautious about commenting on Dudley's current or future contracts.

"You have to treat personnel issues as confidential because there's too much risk of unintended consequences," says David Wynde, a School Board member facing re-election in May. His opponent, Michele Schultz, also would not comment.

DHR International, the hiring firm responsible for last year's national principal search, offers a two-year guarantee on its recruits, according to its website.

DHR didn't immediately return calls.

But responsibility also rests with the district. "The success of Jeff is going to be a key measure of Vicki Phillips' legacy," Gonzalez says. "I would have thought they would have paid closer attention."