PORTLAND POLICE TOOK $150 from a city "evidence fund" to pay for a handjob from an alleged prostitute in a Northeast Portland motel last summer.

When the deed was done, the officers arrested the woman for prostitution. Now the district attorney is attempting to prosecute the case.

Officers from the Portland Police Bureau's Neighborhood Response Team employed the unusual tactic during a prostitution sting at a motel on NE Gertz on August 13, 2009, according to arrest reports obtained by the Mercury.

"I photocopied the money to purchase the sex act prior to departing for the mission," wrote Officer Jack Gillentine, who gave the money to a "confidential informant" who would be on the receiving end of the handjob.

Gillentine arrested the woman when the informant came out, and the informant then described the handjob in an interview with Vice Officer Meghan Burkeen.

"She's reaching over and she's kinda like squeezing my nipples, and, um, and then she reached down, at that point and she starts, um, massaging my, ah, nutsack, so, um," reads a partial transcript of the informant's interview. "So she just kinda like, leans down in there and I don't know, maybe it might have taken a minute, boom, quick finish, that was it. Pretty straightforward, cut and dry."

The case has dumbfounded many in the criminal defense community, who last saw police giving informants city money to ensnare alleged prostitutes 17 years ago, says attorney Scott Stinson. The problem? It's probably illegal.

"Statutorily, there are exceptions for officers in their law enforcement duties to do things like possess drugs," says Stinson, who is defending the alleged prostitute in this case. "But there's no such exception for prostitution-related conduct. Taken in a certain light, the police officers in this case have entered into a conspiracy to commit a crime."

Stinson is trying to find out whom the informant was to see whether he, too, was charged with a crime. But so far, the district attorney's office has kept his identity a secret.

The case has raised eyebrows at the city, too.

"I'll have a conversation with the bureau to see what information they can provide me regarding the sting operation, and to ensure there's protections in place so they're not engaging in misconduct," says Mary-Beth Baptista, director of the city's Independent Police Review.

The police bureau has been struggling to stay within its budget for the year, and Police Commissioner Dan Saltzman declined comment on this story. However, the real question is for the district attorney's office, says Stinson.

"I don't know what their policies and procedures are, but what the DA's office has basically done is sanctioned unlawful conduct," he says.

If the state was holding the informant on other charges and offering him a plea deal in exchange for going to get the handjob, then it's possible the DA's office itself could be charged with compelling prostitution.

District Attorney Mike Schrunk says this is a "relatively rare" procedure, and that such busts are "prescreened by a senior deputy district attorney."

"Would we rather just try clean cases?" he asks. "Sure. But this is not a new issue. It has come up over the years."

"Is it a good use of public funds?" Schrunk asks. "Prostitution as you know exploits women, degrades neighborhoods, degrades people. We usually do these things in order to go up the chain and find the person who's paying for the motel room, paying for the advertising."

Schrunk directed us to the police bureau for a list of the policies and procedures around these kinds of stings.

"We do have written policies around confidential informants in general," says bureau spokeswoman, Mary Wheat. "But not specifically for the prostitution cases."

"It has been in our policy to use informants in prostitution cases," Wheat continues. "But all money used for undercover drug buys, prostitution stings, and other such cases comes from evidence fund money and all that is audited on a regular basis."