When I offered to buy lunch for 19-year-old Jon Maack, he chose the food court at Pioneer Place and ordered a cheeseburger and fries from McDonald's. He wanted to go sit in the square, but I dragged him instead to the Park Blocks, quizzing him about his life along the way.

Our conversation faltered uncomfortably when we arrived and saw two dozen children playing in the clearing. Without a word, we walked on, passing the next block where a teacher led a train of preschoolers on a leash, and finally settled on a bench near the art museum.

You'd never notice how many children there are unless you took a walk with someone convicted of a sex crime.

Jon owes the probation restrictions that bar him from parks and libraries to what he did five years ago, when at age 14 he molested a 9-year-old female relative, eventually coercing her into having sex.

The girl reported the rapes to her parents months later, and Jon was arrested on April 1, 2002, at Thomas Edison High School, a private alternative school. Because prosecutors believed he continued to offend after he turned 15, he was transferred to adult court, where he faced a mandatory minimum sentence of more than 16 years for charges of rape, sodomy and sexual abuse. He eventually pleaded guilty to three lesser felonies, avoiding any serious jail time, and underwent an 18-month treatment program.

Now he's free, except for one thing: He is an adult sex offender and must comply with adult registration requirements and adult probation restrictions. He will have to report his address to the state police every time he moves or turns a year older for the rest of his life. For the same duration, he must confess his crimes on applications for jobs and apartments. And if he violates one condition of his release—by failing a drug test or leaving the state without permission—his probation officer or a judge can lock him up in the county jail or revoke his deal and send him to prison.

Individually, each rule makes sense, offering safeguards against the possibility that Jon will try to hurt someone else. But after spending time with Jon, and adding up the challenges he's faced in the last five years, it's hard not to see that the rules have a circular effect, each prohibition making the next harder to meet. Registration, for example, makes it easy for landlords to block Jon's access to housing, which in turn makes it hard to fulfill another obligation, that he stay employed or enroll in classes full-time.

Jodie Teitelbaum, who runs the treatment program Jon attended, believes registration and continued monitoring make society safer. But she doubts the rules protect us from most sex crimes, 95 percent of which are committed by someone known to the victim. And she struggles with how to arm her charges for the frustrations that lie ahead. "Honestly, I don't know how much you can prepare someone for the fact that they may not be able to find a place to live," she says. "It makes me wonder what we think they're going to do. How are they going to be contributing members of society when they don't really have a chance?"

Standing in the doorway of his Oak Grove apartment, Jon apologizes for the clutter from last night's get-together: empty Doritos bags and scattered video-game cases—Halo, Star Wars Battlefront and Ghost Recon. Grand Theft Auto, he says, "is around here somewhere." Although he is barred from owning pornography or weapons, no rule restricts him from performing fictional sex and violence on an Xbox. He's wearing baggy jeans with slashed knees and an ARMY T-shirt. His black Korn hat hangs on a nail by the door.

Jon's new probation officer recently lifted his ban against using the Internet, a common prohibition for sex offenders. With his new freedom, Jon went online and opened an account on MySpace, the online community that has sparked alarm for putting sexually curious minors within reach of predatory strangers.

Jon's profile is more of an attempt to bury his past. He writes: Right now I'm trying to get my life back on track so I can move on from my past. I'm single and looking for a good woman in my life and friends to hang out with that can be trusted and relied on.

His social life is in transition. He has "a lot of ups and downs" with his best friend, Mike, whom he met in treatment. Mike's girlfriend gets mad when the guys hang out too much and make jokes about being sex offenders. Jon recently started dating a 19-year-old girl and has been trying to prepare himself to tell her about his criminal record.

He works off his frustrations on a weight set made from a bar, a few 20-pound rings, two cinder blocks, four milk crates and abundant duct tape.

Jon describes his neighborhood as "working class, a little redneckish."

The sliding glass door in his apartment looks out on a rubble field with a camper and few broken-down cars, and beyond that, the Bomber Restaurant.

"I could be doing better," he says, "but this is the only place they have for people in my situation to live."

Before he moved in, Jon made a preemptive phone call to the Driftwood Terrace apartments and told the property manager about his offenses. He was surprised when the manager still gave him an application, and then a set of keys.

He knows it's his fault he got into this situation to begin with.

When asked about his childhood and his family history, he rolls his eyes. "Eh, I've repressed all those memories," he says with a smirk.

With a little coaxing, he paints a hazy picture of a modest house on the modest end of Lake Oswego, where he lived with his dad, his stepmother and their children. His father made enough money from the filtration equipment company he owns to keep the family comfortable. But Jon often tells people he grew up in rural Missouri, where he spent summers with his mom. He seems eager to reject "pretentious" Lake Oswego.

Because he has dyslexia, he transferred from one special-ed program to another in school, making it hard to maintain friendships with classmates. He was always small for his age and didn't play sports. By the time he got to high school, he was angry enough to cut himself with bottle caps and knives, leaving thin white scars on his upper arm.

One night, in a bedroom in a house with no adults, he began touching, and eventually having sex with, the 9-year-old female relative. He says he was bored and curious and turned on. He had had sex before with a high-school girlfriend and knew what to do. He continued violating the 9-year-old for several months, Jon says, and then he stopped.

He claims he never used force. The victim's side of the story can't be told here because the courts won't release police reports on the investigation without a judge's order.

The girl, now 14, is no longer in therapy and doing well, according to her father.

In December 2002, in a room in the Clackamas County district attorney's office, Jon's attorney presented him with a deal. Instead of rape and sodomy, Jon would plead guilty to attempted sodomy, attempted sexual penetration and attempted sexual abuse. Rather than serve time, he would complete an $80,000 treatment program at his father's expense.

If the case had stayed in juvenile court, he probably would have ended up in an outpatient treatment program and been eligible to appeal his registration requirement after three years.

Jon's features contract as he talks about the deal. His voice rises, and he speeds up his cadence. "They basically made my mind up for me," he says, "kind of told me, you know, 'This is the only option you have.'"

A few days after Christmas 2002, Jon drove with his father to the Counterpoint Residential and Day Treatment Center in a sm all cluster of wood-framed buildings near McMenamins Edgefield in Troutdale. The program is run by Morrison Child and Family Services.

He joined about 20 other boys, ages 12 to 18, all of whom had committed serious sexual offenses.

"At first I thought, 'Eh, this place is kinda creepy,'" Jon says. "Then I got used to it. You start to notice that you're getting your life back on track."

Of the offenders who successfully complete the program, only 2 percent go on to commit additional sex crimes, according to Counterpoint's own research. (About half of Counterpoint's clients don't complete their treatment, however, and thus aren't included in statistics.)

Counterpoint staffers try to dispel common myths about the perpetrators of sex crimes, juveniles in particular. Most importantly, juvenile sex offenders are far more amenable to treatment than their adult counterparts. They are also less likely to re-offend, either as youths or later as adults, with recidivism rates ranging between 5 and 14 percent, compared with 10 to 20 percent for adults, according to several national studies. Juveniles have fewer victims and are less likely to commit aggressive or predatory offenses.

Counterpoint's group therapy sessions require clients to take responsibility for their crimes. Teitelbaum, now in her 13th year at the center, asks the young men to reveal "how they were able to do it," their fantasies and rationalizations, how they coerced their victims and kept them quiet.

Truth-telling is guaranteed with monthly polygraph tests and questioning by peers.

If the group sensed someone was lying, Jon says, "we'd berate them with questions. Or just call them on it, like, 'That's a bold-faced lie.' We could smell bullshit."

The point of it all is to train offenders to realize when they're in their "cycle," the pattern of thought and behavior that precedes harmful actions, and give them the tools to move in a different direction.

Jon learned to recognize his own cycle—"when I start just thinking about myself, and not caring how other people feel.

"Usually just realizing that you're in it," he says, "you can just step out of it."

Explaining his frame of mind back then, Jon says he knew society considered his actions wrong. But, he says, "It didn't feel wrong."

Now, he says, he knows, and feels, the difference between right and wrong. When he sees a television show that deals with sexual abuse, he "feels as uncomfortable as anyone else."

A year and a half after entering treatment, in August 2004, Jon graduated from Counterpoint. He took a bus back home to Lake Oswego, where his father rented him a one-bedroom in the Hunt Club Apartments. He was 17 years old.

Jon's probation officer had already explained the conditions of his freedom, binding until his probation expires in December 2012. The standard sex-offender package, which includes needing permission to leave the state, came with personalized directions, like avoiding the neighborhood where his victim lived.

If some of the rules seemed vague and open to interpretation, that was by design. Clackamas County's sex-offender probation director, Jay Scroggin, says he wants offenders to question their own actions constantly.

Jon was banned from making contact with minors or frequenting places where minors congregate. His probation officer said incidental contact, like ordering a burger from a teenager at McDonald's, was safe, but he had to steer clear of libraries. The slight leeway requires Jon to make some arbitrary judgment calls: He still goes to video-game stores, for instance, but avoids candy shops and Claire's, a shopping-mall store that sells cheap jewelry.

Despite his confusion over the rules, Jon says he was "full of hope" as he made his first steps back into normal life. He had been planning for months, and dreaming for years, of joining the Marines, and he canvassed the Portland area by bus to visit recruiters. Most said there was nothing they could do; a few told him to get the hell out of the office. While the military occasionally offers waivers to promising recruits with felony records, such allowances are rarely made for sex offenders.

"I was really, really disappointed after that," Jon says. "It's like somebody just takes away an entire life dream."

Instead of joining up, he got a job bussing tables at the Village Inn, a 10-minute bike ride from his apartment. Before work, he attended a high-school equivalency class at Lakeridge High School, pedaling an hour from home to get there at 7:30 in the morning.

Jon had a few early run-ins with his probation officer, who, he says, once berated him for stopping to talk when a relative drove by in a car with Jon's victim in the back. But more than anything, Jon was bored.

One winter night, when he'd been on his own for just a few months, the college students next door invited him to a party and he went. He drank five or six shots of vodka and "got very, very sick." During his next meeting with his probation officer, he confessed. Lying was not an option, since he was due for a polygraph.

It was a serious violation, giving his PO the option of sanctioning him with an array of punishments, from assigning community service to sending him to jail for up to 60 days. She locked him up for one night and ordered several hours of community service plus six 12-hour shifts sitting in the Clackamas County jail over the next three weekends.

"When you're on probation for as long as he is, it's hard not to occasionally violate it," says Dan Cook, a spokesman for Counterpoint who has become a friend and mentor to Jon. Cook believes juvenile sex offenders often fail because they inevitably slip up and get thrown into juvenile detention or prison. He says, "I've even heard these kids at Counterpoint saying, 'I would have been better off killing someone. I would have gotten more of a break.'"

In fact, Jon would have served less time and faced fewer post-conviction restrictions if he had been accused of manslaughter or attempted murder. If convicted of his original charges, Jon stood to serve more than 16 years in juvenile detention and prison under mandatory-minimum sentencing guidelines. Manslaughter would result in 10 years, attempted murder in seven. Neither requires registration, and both would mean fewer restrictions on where Jon could visit and live.

Not long after Jon's 18th birthday, his landlord asked him to put the lease for his apartment, which his father had signed, in his own name. Jon filled out the form, writing "yes" on the line next to the question, Have you ever been convicted of a felony? Days later, he opened a letter giving him 24 hours to vacate his apartment.

"It came as a shock to everybody," Jon says. He couldn't believe the eviction was legal, which it was.

Jon's PO moved him into a room in the Your Host Motel on a stretch of Southeast McLoughlin Boulevard in Milwaukie lined with title-loan outlets and fast-food restaurants. Clackamas County contracts with the hotel to provide emergency housing for sex offenders who would otherwise be homeless.

Jon knew he had to find a new place. But he didn't bother looking for an apartment in the city or close to his dad's place. "There was nowhere else to move," he says. Instead, he rented his current rooms just a few blocks from the hotel. His first trip was to the sheriff's office in Oregon City, where he renewed his sex-offender registration.

His second priority was to find a new job. He'd lost his shifts at the Village Inn because it was now too far away by bike and he couldn't make the commute by bus.

Jon began applying for jobs at fast-food restaurants, always writing "talk about in interview" in the blank left for felony convictions on the application. He rarely got a call back. When he did get an interview, he says, someone else got the position.

Jon signed up for a new high-school equivalency class at Clackamas Community College, but he says his probation officer told him to drop the class because he'd have to interact with minors.

Cook decided to drag Jon to a few friendly job interviews to pull him out of his funk. The first one, he bombed. But in the second interview, Jon got along with the boss, who recommended he look into a skilled trade.

Finally, this spring, Jon enrolled in a welding program at Clackamas Community College. He's doing well in the classes and hopes to make a career of the work.

Compared with many young sex offenders, Jon is lucky. His father's money means he has a safety net to fall back on if he gets evicted again. His father pays his rent and gives him a few hundred bucks for groceries each month, usually in exchange for Jon helping out on jobs pruning trees or clearing bushes.

John Maack Sr. doesn't count his son lucky. "In his case, I believe the system has been too hard," he says. But it's not the restrictions on where Jon can go, or whether he can hang out and drink like a normal, rebellious teen. "The hardest thing for him is carrying a label around for the rest of his life," the elder Maack says. While he was reluctant to have his own name included in the newspaper, Maack supports his son's decision to talk. "If this is something he can change, then maybe he should do so."

Maack says he forgives his son, even though the victim is also a member of his family. "You can't change history," he says. "I feel sorry for both children."

Like many offenders, Jon gripes about the restrictions imposed on his life by a string of probation officers. He doesn't really mind the library ban, but groans that he's not allowed to attend social functions where minors are drinking. Like most 19-year-olds, his friends drink, and although he says he doesn't, he'd like to hang out and not have to worry about telling his PO or getting caught by the polygraph.

"They're telling me to be sociable," he says, "but anytime someone's having a get-together, I can't go."

His probation office shares some of Jon's concerns.

"Part of our mission is to protect public safety. The second part is to rehab the offender and get them back to being productive members of society," says Scroggin, the Clackamas County sex-offender unit supervisor.

Scroggin wants to make it clear that he's not attacking popular legislation, and that registration arms the public with useful information. But he clearly gets frustrated with some of the constraints.

"Some of these laws also make it very difficult for someone to become a productive member of society," he says. "A lot of these people come out of the institution homeless, and there are very few places that will take them in. They're almost taking two steps backward because of what people do when they get access to this information."

While Jon has made progress toward his goals, he can't always restrain his frustration. When I asked him if he felt like he'd been marked for life, Jon shot back, "There's no, 'I feel.' I know. I have been marked. I'm gonna be carrying this around the rest of my life.

"I got what I got coming to me," he says. "But if you are willing to change, then you should be treated differently than the people who don't want to change."

Oregon's Sex Offender Numbers

Total Oregon registered sex offenders: 13,153

Total classified as "predatory"*: 328

Total in Washington County: 1,130

Predatory: 10

Total in Clackamas County: 862

Predatory: 11

Total in Multnomah County: 2,607

Predatory: 63

State police do not track the number of sex offenders who were minors when they committed their crimes but were sentenced as adults.

*offenders who have a tendency to victimize or injure others and have been convicted of a serious sex crime such as rape or sodomy

This spring, the Oregon Legislature passed a version of Jessica's Law, a popular bill sweeping the country that increases sentences for sex crimes against children.

Jon Maack's probation requires that he submit to DNA, polygraph and drug tests and allow searches of his body, vehicle and home—no warrant required.

He needs written permission from his parole officer to leave the state. If he has children before his probation expires in 2012, he will need permission to see them.

Under 1994's voter-approved Measure 11, which established mandatory minimum sentences in Oregon for 21 violent crimes, any juvenile 15 or older who is charged with one of the crimes gets sent to adult court and faces sentences that cannot be altered by a judge.

As part of his treatment, Jon wrote and sent a letter apologizing to his victim.

About 20 percent of all rapes and half of all child molestations are committed by adolescents.

Most sex offenders were not victims of childhood sexual abuse. Likewise, most children who are sexually assaulted do not go on to sexually assault others.