Debbie Woodcock was once a Portland police officer. Now she's a he.

With his stocky build and tendency to sport jeans, work boots and a few days' growth under his nose and chin, Damon Woodcock looks like a former prep linebacker now in blue-collar work. He has a penchant for T-shirts that show off his beefy arms, but you don't realize his strength until, punctuating a joke, he casually backhands your shoulder--a friendly pat that packs a wallop.

It's not obvious, then, that Damon used to be Debbie, and Debbie used to be a cop. In December 1998, when she became a he, his future seemed brighter--except at work. There, the Portland Police Bureau gave him a hostile reception, sparking a legal battle that lasted more than two years and officially ended last month.

Throughout that time, Woodcock has only once commented publicly on his case, in a brief interview with Just Out almost two years ago. Last month, he decided to break his silence with WW.

His story provides a glimpse into the macho culture of the PPB as well as the little-known world of transsexuals, many of whom consider Portland a national mecca.

It's a tale with contested facts and dueling ideologies, with disagreements on everything from whether Woodcock merits a male pronoun to whether he deserves the $205,000 the city paid him two weeks ago. What's undisputed is that last month, when he opened his mail and found the check that made his resignation final, Portlanders lost a very good cop.

"Everybody said she was a wonderful officer," Mayor Vera Katz told police and city officials in a closed-door meeting in April 2000, discussing Woodcock's case. "Quite frankly, I think the bureau botched this one."

As a young girl growing up in Beaverton and Newberg, Debbie Woodcock shunned Barbie, preferring her brother's plastic soldiers. "I hated dolls," says Woodcock. "I always wanted the guns and the trucks."

"Even as a child, people thought my sister was a boy," says Woodcock's sister, Jennifer. "She's always been --I don't know what the right term is--unisex."

The recognition that some people identify with the other gender dates back to at least the fifth century B.C., when the historian Herodotus described cross-dressing among Greek men. Closer to home, the Navajo culture even honored hermaphrodites, people of mixed sexual organs, for their wisdom.

But even as western society has grown increasingly tolerant of homosexuality, the concept of transsexuality remains baffling for most of us. We laugh nervously at the comedy of RuPaul, don't know much about transsexuals--and don't particularly want to learn more (see "A Trans Guide for Idiots," page 23). There's even confusion on basic lingo: "Transgender" is a broad term for all sorts of gender bending, including guys who start wearing lipstick and want to be called Bobbie, not Robert. "Transsexuals" are people who undergo surgery while changing sex, typically by changing their genitalia and/or breasts.

What seems like a radical transformation is based on a conviction that at birth, their gender was a mistake. For some transsexuals, the awareness of their "otherness" doesn't settle in until later in life. For others, like Woodcock, it came much earlier. "I have always felt male," he says. "When I was 3 or 4 years old, I felt that I should have had a penis."

At Sunset High School in Beaverton, Debbie Woodcock, an A student, was attracted to both girls and boys. After graduating in 1978, she attended Oregon State University, studied computer science and became a practicing bisexual. She dated a member of the women's softball team at OSU without telling her mother or her father, a Presbyterian minister.

After getting her diploma in 1982, she went into computers and did bookkeeping for companies in the wood-products industry. She dated guys to please her parents, who were pressuring her to marry. Eventually, however, she started dating women again, and the pressure stopped. Woodcock thinks they figured it out.

In 1985, Woodcock felt drawn to police work, so she signed up to become a reserve officer for Portland--essentially an unpaid volunteer who gets to carry a gun and drive around looking for bad guys. Being a cop was "great fun," Woodcock says. "You have so much power, and you have so much freedom. I loved it."

The bureau, in turn, loved her. Her work as a reserve brought a half-dozen commendations; in 1990, she issued more tickets than any other cop, regular or reserve, during the summer cruise crackdowns.

In 1991, she became a full-time cop, passing oral, written and physical tests and finishing second in her class in basic training. In 1993, while she was temporarily assigned to the traffic division, Sgt. M.F. Roberts awarded her a commendation, saying she "routinely" did twice as much work as the average cop. A year later, Woodcock received a commendation for helping capture a serial stalker.

She was tough but compassionate. In 1996, the director of the Salvation Army's Greenhouse shelter wrote a letter to Central Precinct, praising Woodcock's assistance to a frightened 13-year-old runaway girl who had been abused. "I cannot tell you how impressed our entire staff was; we had not the opportunity to witness such expertise from a law officer before," Debbie Coppenger wrote. "You must be very proud of this young woman who is such an asset to your force. Her integrity, diligence, and an ability to impact our community in a positive way are exceptional."

But in the mid-'90s, Woodcock's love affair with being a cop began to sour. Working Central's afternoon shift, she noted that plum assignments, like the Rose Festival, seemed always to go to men.

Officer Lori Smith, who was stationed elsewhere, says she has heard from women besides Woodcock that "it was the pits being female at Central...and it sounds like it was worse on afternoons."

Being lesbian didn't help. Though overall the bureau is viewed as being relatively tolerant of lesbians, some assignments were better than others. Asked about Central Precinct's atmosphere for sexual minorities in the mid-'90s, Officer Dawn Urban told city officials at a March 2000 hearing that "it stunk.... There were some pretty blatant comments."

Sick of getting passed over for choice assignments, and suffering from fits of rage and anxiety, Woodcock thought about quitting her job.

Then, in July 1997, she made a discovery that would change her life: a lump in her breast the size of a golf ball. It turned out to be just a cyst--but it scared her and sparked a realization, recalls Woodcock: "I never wanted these things anyway."

In deciding to become a transsexual, Woodcock arguably could not have chosen a better location. When it comes to trans-friendly cities, Portland "is one of the best, if not the best," says B.J. Seymour, a Portland counselor who advises people considering sex-change surgery. "Portland is kind of a mecca for transsexuals." Lori Sirotsky of the National Transgender Advocacy Coalition says the Rose City "is generally considered to be very trans-friendly."

No one keeps track of numbers, but Portland's trans population is estimated to exceed 1,000. Trans activist Lori Buckwalter attributes the city's allure in part to its trans-friendly policies. Portland is one of the few major cities that have outlawed bias against transgendered folks. Sexual minorities enjoy a written "partnership" agreement with the Portland Police Bureau to ensure equal protection under the law. Oregon, unlike most states, investigates claims of discrimination against transsexuals.

Reid Vanderburgh, a transsexual therapist who recently returned to Portland to set up practice after three years in San Francisco, says Portland is more tolerant of gender ambiguity than many cities. "Having gone from here to the Bay area, I would much rather come here," he says. "The ambience in Portland in general is friendlier, and that translates to how trans people are treated."

Another attraction is the presence of Dr. Toby Meltzer, who's considered one of the best sex-change surgeons in the country, if not the world, according to Denise Leclair of the International Foundation for Gender Education. The presence of Meltzer, combined with Portland's "transfriendliness," has given rise to a cottage industry of doctors and therapists to serve them, numbering at least 20.

Such support is important because, under professional guidelines of the sex-change industry, every transsexual is supposed to undergo a year of counseling and living as the opposite gender before undergoing surgery.

Woodcock began seeing B.J. Seymour in October 1997, and started going by Damon that December. He began a twice-monthly regimen of testosterone shots, which halted menstruation and seemed to reduce his job-related anger as well.

It also affected his social life. Woodock found that once he went on testosterone, some of his lesbian friends no longer wanted him around, complaining about his "male energy."

That's typical, says Vanderburgh: Many gays and lesbians view a sex change by their peers as betrayal. Even many transsexuals don't like hanging out with transsexuals, because they want to assimilate and think of themselves in their chosen gender, Vanderburgh says. "This is a transient population in terms of the identity itself, and that is a real difference between this population and the gay and lesbian population," he says.

Perhaps this is why there are no trans bars in Portland. Rather, some trans folks will hang out at gay and lesbian bars like the Embers, Scandals and the Egyptian, especially early in their "transition" when they don't feel sure of their ability to pass in the outside world. Woodcock belongs to a trans mailing list of people who used to hang out socially but haven't done anything in months. He lives with his partner, Darren, with whom he's been for eight years.

In December 1998, Woodcock checked into Eastmoreland Hospital, a small, 100-bed facility next door to Reed College, and had his breasts removed at a cost of $6,000. (He's postponed the genitalia surgery, a more expensive process.)

Asked if there's a lot of scar tissue from the breast removal, Woodcock lifts up his turtleneck to reveal a couple of dime-sized liposuction scars. But that doesn't mean it didn't hurt. "This whole area was one big bruise," he says, outlining a section from his neck to the bottom of his rib cage. "I couldn't even get up out of bed."

At first, looking at himself in the mirror was weird. Still, he felt like he was finally on the road to becoming the person he always was. The testosterone was working, changing his jaw line, his voice and his body shape.

But Woodcock knew the real test would be back at work, in a bureau where talk of diversity hasn't translated to the roster. Of the bureau's more than 1,000 sworn cops, 84 percent are male, 90 percent are white, and roughly 95 percent are straight.

Woodcock's sister, who still refers to him as Debbie, does not think he foresaw the problems that lay ahead. "I think she somehow thought that this would make it better [at work], and I don't know if that was realistic," she says. "I think she may have been a little naive."

In fact, Woodcock had reason to hope for a smooth switch: He was not the bureau's first. A few years before, another woman cop had undergone a sex change. This officer did face some resistance among colleagues, sources say, but the transition was eased by a transfer off the street to a job at headquarters, where the cop was given a locker in the chief's 15th-floor offices.

But the timing for Woodcock could not have been worse: Tensions were running high at Central, thanks to one of the largest internal probes in the bureau's history, dubbed Centralgate.

In February 1999, officers had come forward with claims that cops at Central were leaving shifts early without punching out and were getting bogus overtime payments. Other allegations included drinking on the job and having sex with informants.

On May 19, Woodcock met with Internal Affairs and told them that Central Precinct was out of control, confirming the timecard problems and complaining of sexual discrimination.

Three days later, it happened: Woodcock sat at a desk at Central Precinct, filling out reports with his back to four other cops. One of them, Kelvin Knudson, loudly told his coworkers that Central was full of "fucking rat snitches," saying he had a bullet for every snitch at Central.

Woodcock reported Knudson's comments to Internal Affairs, saying he felt Knudson was intimidating potential witnesses for the Centralgate probe.

In addition to fearing for his safety, Woodcock was fretting about the locker-room switch. He'd asked then-Chief Charles Moose for a transfer to the cop shop's Tri-Met unit. Instead, Woodcock says, Moose gave him a deadline: get his "transition" completed by July, so a new batch of female recruits entering the women's locker room wouldn't be confronted by a man.

On June 26, with Centralgate tensions running high, Woodcock changed locker rooms. He still remembers the first day, moving his stuff in at 11 am when the room was empty. At the end of his shift, he returned to his locker, running into a male cop whose "jaw just dropped."

"I knew it would be uncomfortable, for them as well as me," says Woodcock. "That's why I requested the transfer to Tri-Met."

Woodcock says that for the first few days he avoided making eye contact in the locker room and never stripped below a T-shirt. He says people started showing up for roll call in civilian clothes, a sort of silent protest.

Then, on one of Woodcock's days off, between June 29 and July 1, someone used a ballpoint pen to draw a circle and a slash-- the international "no" symbol--through the "cock" in Woodcock's last name.

Some cops would later dismiss it as harmless. But a fellow officer saw it as inappropriate and reported it to Internal Affairs. No one, however, told Woodcock, who found out about it through a friend days later. In the wake of the Knudson "bullet" statement, Woodcock viewed the vandalism as more than a prank, and promptly took a week's leave.

When he returned, he found that there had been no apparent investigation of the incident. In fact, on the very day he came back, Assistant Chief Mark Paresi came down on him, for wearing a tongue stud--though several others who wore them were not confronted, Woodcock says.

The next day, Chief Moose chewed Woodcock out, claiming he'd never instructed him to change lockers. (Officer Katie Potter would later testify that the chief had also told her Woodcock needed to move.) Moose also told Woodcock he could move to Tri-Met if he wanted to, but Woodcock declined. He says that if he had accepted the transfer at that point, it would have made it easier for the bureau to drop the probe.

Instead, Woodcock went back out on leave, citing anxiety over his belief that the department was not taking seriously a possible threat to his life. Lori Smith, who is African-American, says if that someone had done the equivalent to her locker by drawing a noose, "I think it would have been looked at as a hate crime."

Smith, who served in a peer support role for Woodcock at the time of the incident, thinks that the legal hullabaloo never would have happened "if sergeants had come and said, 'This is what happened, we're going to look into it. We're sorry this happened to you.'

"But to not even mention it to somebody when they come back, that's just wrong," says Smith, who spoke to WW at Woodcock's request. "And to start addressing the tongue stud would make me feel like I was the target instead of the victim."

In July, Woodcock applied for a temporary disability payment from the city's Fire and Police Disability and Retirement Fund. The FPDR hired Sandra Pinches, a clinical psychologist, to provide a diagnosis. She found that, although Woodcock had some preexisting anxiety, the bureau's handling of the situation had clearly made things worse. "Among the most threatening points in [sex changes] are switches in...restrooms and locker rooms," she wrote. "Coercing a transgendered person to take the risk of switching restrooms or locker rooms before he or she is ready is like pushing from a high diving board a person who is just learning to swim."

One of Woodcock's biggest concerns was that if he responded to a dangerous call, his fellow officers would respond slowly to back him up--or not at all. In cop lingo, this well-known phenomenon is called "slow cover" or "no cover." In September he requested a desk job, but was told no dice.

Meanwhile, the FPDR board began discussing the issue in a series of closed-door meetings. Transcripts later obtained by Woodcock showed that his transgendered status worked against his stress claim. City Auditor Gary Blackmer said of the sex change, "You have to expect that you're going to run into difficulties and that things are going to happen, some of it in the workplace." Others, such as police-union official Leo Painton, said Woodcock's case showed the downside to the bureau's diversification efforts.

Some board members said Woodcock's fears were brought on by a preexisting mental disorder--the extreme anxiety experienced by many people changing their sex. But Woodcock's attorney, Lynn Nakamoto, deployed several witnesses who testified that Woodcock's fears were well-founded.

Several cops testified to the hostile environment toward sexual minorities that existed at Central. Some also testified that cops who snitched--including Woodcock -- had legitimate reason to fear retaliation by fellow cops. For example, one cop who was perceived as blowing the whistle on Centralgate was given a one-month leave for his own safety following Knudson's "bullet" statement.

Dawn Urban testified that she was once placed on protective leave after turning in two fellow cops, one for keeping dope seized on the street and the other, a sergeant, for asking her to write a false report. She started getting calls at home: "Look out your door, I'm going to kill you."

Detective Amber Lewis viewed the locker vandalism as a "death threat"; and the subsequent investigation appeared designed to "cover it up."

But on April 11, 2000, the final day of the hearing, then-Capt. Bret Smith, head of Internal Affairs, attacked Woodcock's case and claimed the Clark County District Attorney was investigating Woodcock for illegally taping a phone call with a potential witness. In the end, the board deadlocked at 5-5 and denied the claim, with all three Police Bureau representatives voting against him.

Woodcock appealed the decision in court, noting that under the city charter, a tie vote at FPDR did not equal a loss. He felt that he was a victim of dirty tricks--especially after he learned that on April 4, a week prior to Smith's testimony, Clark County had notified Smith's subordinate that Woodcock had broken no law.

Woodcock spent his days marshaling documents and facts in letters to the city. He besieged the city and the police union--which was not helping him--with a series of public-records requests. He analyzed the documents, pored over the Internal Affairs investigation, memorized the police-union contract.

In August 2001, the FPDR board ordered a new psychological examination. Pinches noted an increased level of paranoia and blasted the city's handling of the case as highly damaging to Woodcock: "He is at risk for even more serious complications if the litigation in which he is embroiled is not settled soon."

FPDR relented and approved the settlement. Still, Woodcock does not consider it a victory, noting that his lawyer will get $70,000 and he may have to reimburse his insurance company another $25,000 for medical expenses; meanwhile, he gets no extended disability and must drop all claims against the city.

Woodcock's sister says she is amazed that Woodcock was able to prevail to the extent that he did. But she fears that the ordeal has "broken" him, and she doesn't know if it was worth it.

Woodcock doesn't know, either. He still has frequent nightmares about fighting with people, and he has experienced memory loss, which his doctor says is symptomatic of extreme stress. It's hard for Woodcock to leave his house. "Every time I see a police car I get uncomfortable," he says. "I get angry."

At the same time, Woodcock misses being a cop, which for him was far more than a job. "I really don't feel like I have many friends anymore," he says. "When you get so ingrained into the bureau, you tend not to have very many non-bureau friends. It just becomes harder to relate to people who aren't part of that and don't get it."

Woodcock's experience would seem to indicate that the Portland cop shop, perhaps the city's ultimate boys' club, has a long way to go in dealing with diversity. Yet, there is a counterpoint. In August 1999, the bureau hired a third transsexual, one who had already undergone male-to-female surgery. That officer, who asked not to be named, told WW, "I've had no problems here, actually.... This has been an incredibly accepting place to work."

It's clear that Woodcock's locker-room switch, coming at a time when his supervisors were distracted with Centralgate and some colleagues viewed him as a "snitch," created a volatile situation which the bureau, to quote the mayor, "botched."

Lori Smith says the Portland Police Bureau has made strides in improving the work culture for women and minorities. "To be honest with you, I think it's changed a lot," she says. "I think sometimes the expectation is for that culture to change real fast, and I don't know if that's necessarily fair."

That's not to say, however, she thinks Woodcock's treatment was excusable. "Damon was a good officer before, and I think he would have continued to be a good officer," adds Smith. "I don't think his change should have made a difference in how he was treated."

Or, things we sometimes didn't want to know but felt we had to ask.

What pronoun do you use with these folks?

Once people decide to change genders, then it is polite to refer to them in that gender; trans folks tend to extend that gender backwards, as in "When he was a girl, his friends didn't understand."

How does male-to-female surgery work?

Transsexual surgery basically consists of rearranging stuff. For male-to-females (MTFs), a surgeon creates a vagina. The six-hour procedure entails removing the testicles and cutting out the spongy tissue at the base of the scrotum. That creates an aperture which is then lined with the inside-out skin of the penis, thus retaining the penile exterior's densely clustered nerve endings. Erectile tissue is used to simulate a clitoris above the vaginal opening, and the skin from the now-empty scrotum (often removed of hair through pre-surgery electrolysis) is used to fashion realistic-looking labia around the opening.

How does female-to-male surgery work?

Because constructing a fake phallus is expensive (from $15,000 to $50,000), many female-to-male (FTM) transsexuals settle for amputating the breasts and going on testosterone treatments. They can have their reproductive glands and organs and even their vagina removed, sewing up the aperture and rearranging the urinary tract so they can urinate standing up. The easiest way to have a penis is to get what's called clitoral-release surgery, in which the tendon at the base of the clitoris is cut to let it protrude more; under testosterone treatment, the clitoris grows as long as three inches. For some women-turned-men, this is not enough. They have a section of their forearm or stomach removed to create a larger penis. To simulate an erection, they have to insert a plastic or wooden rod in its base. This procedure has a high risk of complications.

How do the hormones work?

FTMs take testosterone shots, usually self-administered. The effects are like hitting puberty, and result in changing facial and body contours and a deeper voice. MTFs take estrogen pills, which can result in softer body contours and larger breasts.

Do transsexuals have orgasms?

"Yes, a lot of people do," says Dr. Ann Lawrence. "I just did last night." The Seattle-based physician, herself a transsexual, says the medical literature shows that up to 80 percent of MTFs are orgasmic "at least part of the time." The orgasms are aided in part by the male prostate gland, which is considered equivalent to the female G-spot. For FTM transsexuals, it depends on the type of surgery, but many can have orgasms; their overall sexual satisfaction actually improves after surgery, Lawrence says, "in part because they're on testosterone."

Do transsexuals ever have regrets?

Transsexual surgery is pretty much irreversible. But anecdotal evidence as well as some research shows that most transsexuals are happier with their new bodies than before. According to Lawrence, a recent study from the U.K. shows that the vast majority of the male-to-female transsexuals are satisfied after surgery, with none expressing outright regret.

Who gets sex-change surgery?

Lawrence knows of people who underwent the surgery as young as 18 and as old as 70. Portland therapist B.J. Seymour says he counseled a male small-town fire chief who waited until retirement to make the switch. Past studies have suggested that men are far more eager to become women than the other way around.

Doctors estimate that one in 10,000 males and one in 30,000 females undergo sex-change surgery. The Portland Police Bureau, until recently, had three transsexuals among its 1,000- plus cops.

The American Psychiatric Association stopped classifying homosexuality as a mental illness in 1973 but still considers transgenders to suffer from "gender identity disorder."

Dr. Toby Meltzer, a noted Portland plastic surgeon specializing in sex- change surgery, does not grant media interviews, according to assistant Linda Takata.

For one gay man's take on transsexuals, see Queer Window, page 58.

In 1918, an Oregon medical student named Lucille Hart became the first documented transsexual when she got a hysterectomy to prevent menstruation and pregnancy, then changed her name to Alan.

Damon Woodcock says a cop called him at home in July 1999 asking if he had a vagina. During the internal affairs probe, other officers reported some colleagues demanding "no vaginas in the penis locker room."

Woodcock's androgynous appearance drew public remarks "every day that we worked together," Officer Robert Bustamante later told city officials. "He took it in stride."

Staff of the Fire and Police Disability and Retirement Fund recommended approval of Woodcock's claim, noting that two other cops who overheard Kelvin Knudson felt his comments about "snitches" were serious threats.

There are an estimated two dozen openly lesbian officers in the Portland Police Bureau. The best-known is Katie Potter, daughter of former Police Chief Tom Potter.

There is only one openly gay male officer in the bureau, Capt. Mike Garvey, who heads Tri-Met's cop detail.

In November 2000, FPDR attorney Susan Dobrof succeeded briefly in getting Woodcock's appeal dismissed; it was reinstated after the judge learned that Dobrof had given Woodcock's attorney only one hour's notice of the hearing.