Key Bank.JPG

The surveillance photo from a Key Bank in Tualatin that provided Ryan Homsley with his Where's Waldo Bandit nickname.

(FBI)

PORTLAND — The Federal Bureau of Investigation called him the "Where's Waldo Bandit" partly because that's what the feds do — dream up pithy nicknames for bank robbers to cajole the media into covering otherwise mundane shenanigans — but also because Ryan Michael Homsley was a Waldo doppelgänger, right down to the striped sweater and thick-rimmed black glasses Key Bank surveillance video showed him wearing.

But the Waldo moniker fit Homsley (and captured the nation's attention) for another reason, too: this guy didn't look like a bank robber. At 29, he looked like a Portland hipster; like a harmless, hapless chump you might find pulling espresso shots at Stumptown or bagging groceries at New Seasons. Downright friendly, even. And he definitely didn't seem to have any idea what he was doing.

That's a pretty fair description of Ryan Homsley, it turns out. In a four-hour one-on-one interview, Homsley opened up about his sad and strange transformation to Waldo, what life inside an Oregon penitentiary is like for a minor celebrity and how he hopes to redeem himself one day. (UPDATE: Homsley was sentenced Tuesday to five years in federal prison for a second bank robbery.)

Homsley had only a vague idea about how to rob a bank, and he had only decided he was going to rob a bank about 30 seconds before walking into the Tualatin branch of Key Bank on Sept. 21, 2010. Even when he stepped into the lobby, Homsley wasn't sure what he would say or do to convince the teller to fork over some money, or how he would escape. He was making it up on the spot.

What he came up with, after some rapid-fire deliberation, was a haiku. He thought that would be funny. But by the time he got to the island where they keep the deposit slips, he'd forgotten it. Instead, he wrote: "All the money or boom."

Homsley then strolled up to the teller and handed over the note, setting a black box on the counter next to him. She looked down at the note, over at the box, up at him and rolled her eyes. The teller said nothing more, stuffed $505 into a bag, passed it back and Homsley walked out the door. He left the box and a small backpack in the bank.

This heist was supposed to be the culmination of what was always a terrible plan. It was also supposed to be the first and only bank Ryan Homsley would ever rob.

Breaking bad

Four years later, it still doesn't make much sense, that this intelligent, articulate and artistic guy who once held down a steady job as a Blue Cross claims associate would one day see his mug on the television news. His story went viral: Newspapers across the globe featured sardonic pieces on his amusing countenance and crime. The obvious reason for his fame was that striped sweater. But it's worth considering another reason we tuned in to Waldo's plight. He looks not only like that children's book character but also like an ordinary dude. Like many of us. You had to wonder: "What happened to this guy?"

Homsley can be abrasive and irritating, but there's nothing scary or slimy or tough about him – even after his first prison bid. He doesn't seem capable of serious crime. He's like Waldo — or, what the venerable children's book character Waldo would be if he had come from a terrible childhood.

"He could have gone to art school," his sister, Kelly, said in an interview with The Daily Beast, shortly after Homsley's first arrest. "He was that talented. He just got lazy. He screwed up his life."

Only when you consider the totality of Homsley's broken life, of each separate event that led up to that September day in 2010, only then does it begin to click, this self-described "pacifist" threatening to blow up a bank. Homsley had become desperate. Piecing his saga together provides a rare look into the mind of a troubled soul who will either disappear into the system or find a way to crawl out of it. It's make-or-break time for Waldo.

Homsley comes home

Homsley was born in May 1981 in Portland, to an insurance claims adjuster (mom) and an electrician (dad). The couple met in Hawaii, where they lived in a "hippie commune" that specialized in the trafficking and abuse of all manner of drugs — "mom used to tell jokes about how I was conceived on a $70,000 bundle of cocaine," he says — but the family moved to Myrtle Beach, S.C., when he was an infant, to be closer to his mom's parents.

It wasn't until two decades later that Homsley returned here, at the end of a Greyhound bus trip that lasted two years, taught him how to be homeless and how to scam his way into a free bed in any hospital room in America.

It was his brother, Noah, now a program manager at a Portland radio station, who inspired Ryan to return to Stumptown. There was at least for a short time a couch upon which to crash. And after the horror story Ryan had lived, he figured he might be able to lean for a while on one of the only family members he had left.

A horrific childhood

Homsley's father hurt his neck on the job when Ryan was an infant. Before long, Ryan says his dad was taking painkillers. He spent most of his time watching television — or terrorizing his children, Ryan says.

Homsley did his best to escape from his father with a pencil and paper, retreating into his art. He grew up a chubby Goth, a black-trenchcoat-type kid, listening to Nine Inch Nails. The day after Columbine, he says he wore a Hawaiian shirt to school, hoping his classmates wouldn't associate him with the killers. They did, anyway.

Doctors gave Ryan a diagnosis of Type One diabetes when he was 10, after he started urinating "pure Kool-aid," the result of an alarmingly high blood sugar level. He remembers stepping into the bathroom to use the toilet, missing the rim and peeling his foot from the sticky floor. He was sleeping 18 hours a day.

The "honeymoon" stage of his illness lasted three years. By 13, his diabetes was full-blown, and a lifetime of required insulin shots would follow. "Every time my blood sugar drops, my body spits out adrenaline — cortisol, leading to adrenaline," as Homsley describes it. "My heart beats 150 beats per minute. Extreme thirst. Frequent urination. Dizziness. Vomiting. Sleeping 20 hours a day. It's like a walking coma."

Homsley spent two weeks learning everything he could about diabetes, including how to inject himself with insulin. By 16, Homsley says he was shooting heroin, too. He met his future wife, Amber. They married at 20. Homsley considered himself "happy, for the first time in my life."

It would be a short time, though. The couple split up not long after the wedding, and Ryan's mom died in 2005, when he was 24, of a pulmonary embolism.

The one-two punch of his divorce and his mom's death turned Homsley into an agoraphobe. Columbine awakened him to the country's "schizophrenic culture, foaming for blood," he says. He convinced himself he would be shot if he went outside.

Still, he had strung together a decent existence, working full-time as a claims associate for Blue Cross in Myrtle Beach, the same place his mom worked.

"I listened to REM. I wore a tie. I went to the movies Friday nights," he says. "It was a mundane, middle-class life."

No help from God or sobriety

After his mother's death, Homsley stopped caring about that job. He would walk by her desk and see it empty. He gradually began to check out, approving claims he should have denied, showing up late. He was fired.

Homsley tried god and sobriety for a while at a rescue mission in Greenville, S.C., feeding homeless people. It didn't take. Then, an epiphany: Armed with only a USA Today weather map, Homsley decided to get on a Greyhound bus in 2006 and see America. "I was sick of being afraid," he says. The journey would revive his art. But it also taught him how to be homeless.

Homsley figured out pretty quickly that you could get a Greyhound bus ticket from just about any hospital in America. He also figured out how to get admitted into any hospital in America.

"I'd either take too much insulin, or not enough," he says, and then walk into an emergency room on the verge of hypoglycemic shock. "I'd say, 'You've got about 15 minutes.' Sometimes they'd have to keep me in the ICU for three days."

He spent two years on the bus, earning money by surreptitiously drawing portraits of other passengers, then offering to sell them for $10 or $20 a pop, or just leaving them on the seat, as "Easter eggs."

He shoplifted Red Bull (for the sugar hit) from convenience stores, found out where the free meals were in each town he visited and used a food stamp card to cover the rest. He slept in bus terminals or hospitals, where he would stock up on insulin and painkillers.

The trip ended across the country, in Portland.

Homsley thought he could lean on his brother here. He was born in the city, liked it here and knew he needed a fresh start. But he was also a vagabond. He moved to Noah's place, but his (self-professed) penchant for pointless lying quickly wore out his welcome. In August 2008, Homsley spent his first night under a bridge.

Officially homeless

That first time was sort of mythic, Homsley remembers. It was early August, and he'd spent the evening watching the Red Bull Flugtag — where people attempt to "fly" human-powered Rube Goldberg contraptions — at Tom McCall Waterfront Park. He hadn't really planned to spend the night there, but at the end of the evening he just drifted off to sleep, right there beneath the Hawthorne Bridge.

"I was thinking, 'This is as good as it gets,'" he says. "The hard life."

Homsley was officially homeless.

He didn't have it that bad, really. Homsley wore a black dress shirt and carried only a small backpack so that people couldn't immediately identify him as a bum. He sold sketches on the MAX the way he had on Greyhound buses, earning as much as $200 by noon. It would have been plenty of money for rent, but Homsley preferred to spend his earnings on drugs. He stopped working every day as soon as he had enough dope to last him for the next 24 hours or so. Xanax or Demerol to go to sleep; cocaine to wake up.

"I have this belief that some people live better with chemistry," he says. "Some people actually function on drugs."

Homelessness wasn't the Cannery Row romance he'd pictured, though. It was a life that promised a kind of freedom, devoid of societal constraints and rules, but the homeless live by their own code. They claim their spots. And the line outside the free meals was terrifying. "I've seen people knifed, beaten to hell," Homsley says, "for doing nothing but look at people in the eye the wrong way."

To supply his insulin, Homsley kept pulling his emergency room stunts, two or three times a week, he says. It didn't take long before the nurses at every hospital recognized him. They're legally obligated to keep people who walk through the doors from dying, and Homsley exploited that mandate. But lifestyles like this don't last forever.

Homsley says he heard once that when a homeless person died, their body was burned and the ashes thrown in a shoebox and then stuffed into a closet. That's not how he wanted life to end.

And then one day a fellow vagrant told Homsley about "Club Fed."

That's the ticket, the dude said. Do a few months in jail, get clean, get released to a halfway house where they help you find a job.

"How do you get in there?" Homsley asked. The other guy replied: "You got to rob a bank."

It sounded like just what Homsley needed. He wanted help, but had no idea how to find it. He'd burned all his bridges at various social service agencies around town. His friends were fellow vagrants. He'd lost contact with his family. So he decided to walk into a bank and scribble a note.

An easy heist

The dumbest thing about Homsley's bank robbery was that black box — which actually contained hypodermic needles, a spoon and a lighter — and that "boom" in his note, which automatically added "threat of death" to his charges and 18 months to the sentencing guidelines. The teller would have handed him the cash in her till whether he'd threatened to blow the place to smithereens or simply asked for it nicely. That's how easy it is to rob a bank.

The smartest thing about Homsley's first bank robbery may have been what he did right after walking out the front door. He says he pulled off that gaudy striped sweater and dropped it in a trashcan. He removed his glasses, walked calmly across the street to a Peet's coffee shop and ordered a macchiato. Homsley sat there as the cops pulled up to the bank. He watched them stretch yellow police tape across the front, watched them interview witnesses. And before they made it to the coffee shop, Homsley strolled out, hopped a cab and headed straight for downtown, in search of some smack.

It didn't take long for Homsley to find a fix: a "hondo," a gram of Honduran smack available cheaply across the city. He scored, shot up and floated around town, expecting to be snatched up at any moment. His photograph was all over the Internet. Esquire dubbed him the nation's best-dressed bank robber. Waldo was viral. He wasn't trying to hide.

But Homsley wasn't turning himself in, either. He knew going to jail would mean kicking dope, a thing he wanted to do but wasn't exactly looking forward to doing. So he wandered the streets, enjoying his infamy, wondering when he'd get busted.

That took a surprisingly long time, likely because Ryan Homsley really does look like Waldo.

The "Where's Waldo" books' premise is simple: Each double-page spread contains a collection of illustrations of people goofing around in one way or another, often in a well-known locale. Somewhere in each picture is Waldo in that trademark red-and-white striped sweater and matching beanie. Hiding in plain sight.

It's no Rubik's cube, these children's books, but it does take a few minutes to find Waldo on each page because there's so much going on. You have to really be looking for Waldo, for that loud striped sweater, hat and glasses, to have any hope of finding him.

Now, imagine if Waldo junked his sweater in a trash can after robbing a bank, and you had to find him on those pages full of people wearing a boring T-shirt or a black jacket.

Imagine you weren't looking for him.

Catch me if you can

After a few days on the lam, the heroin Homsley had been injecting into his arm so regularly left an abscess on his shoulder, as it had a half-dozen times before. He knew that meant checking into a hospital, having it popped and packed; a painful ordeal that wouldn't be accompanied by painkillers. Homsley had an abscess on his hip, too. Both were growing, and both were increasingly painful. He knew he needed treatment. But he also knew he would be recognized at any hospital in Portland. So he put it off until the abscess had grown so large it prevented him from drawing.

Homsley decided to start pressing his luck. He claims he walked right up to a Portland police officer and asked where to find Voodoo Doughnuts. The cop gamely offered directions to the shop, he says.

"I was having fun with it," he says. "And I was scared of getting clean. How long can I stretch $400 worth of Hondo dope?"

Occasionally, Homsley spotted a local television news story about himself.

"I saw myself on Fox Most Wanted," he says. "The guy was laughing about it, like it was a joke. I was now the joke of Portland."

Homsley began daring the cops to catch him. He logged onto Facebook and posted a link to the bank robber story, with a mug shot anyone would be able to recognize as him. No one commented, so he grew more brazen. "The wheres waldo bandit (sic) strikes again!" he wrote. Then, "money money money." Then, "db cooper was a great man... the wheres waldo bandit will be better. see ya gys in seattle next (sic)."

Later, he tried to justify the crime with, "I'm doing this to pay for my medical expenses... live for today!" Then, a video by the Fun Lovin' Criminals that depicts a bank robbery, coupled with the heading, "This is the song I hear in my head when I did it." And finally, a confession: "I'm now a bank robber." A friend replied, "somehow I am not surprised."

Homsley changed his profile picture to that bank surveillance photo.

After three full days wandering the streets of Portland, Homsley finally was recognized, he says, by a homeless girl sitting on the street in front of the downtown public library. She looked up from a heroin nod, right into Homsley's eyes. She pointed at him, and said, "Waldo." He gave her a $100 bill. "I walked away."

He was getting away with the bank robbery, which wasn't part of the plan. And his abscesses were getting worse. So Homsley caught a Greyhound to Eugene, an hour and a half south of Portland, and checked into Sacred Heart Medical Center.

Touch my badge, Waldo

At Sacred Heart, Homsley figured he would receive treatment for the abscesses and then sneak out before anyone recognized him as Waldo. But by the time he actually made it there, the wound was so bad that it required surgery to prevent his arm from having to be amputated. When he awoke from the anesthesia, Homsley realized he was handcuffed to the hospital bed. He could see two federal agents waiting outside the room.

"Hey, how you doing there, guy?" the agent said after Homsley woke up. He took out his FBI badge and handed it to Waldo. "You want to touch a real fed badge?"

Homsley knew the jig was up.

Club Fed

"Yeah, I'm the Where's Waldo Bandit," he said. "You got me."

Waldo kicked heroin in the Lane County Jail.

Examples of Ryan Homsley's art work appeared in a federal sentencing memorandum in July 2012.

In jail, the sheriff's deputies called Homsley, "Waldo," to mock him. This made him angry, but his plan seemed to be working. He started a zine called "Cloud Factory." He was on his way to Club Fed, to serve a three-and-a-half-year sentence at the medium-security Federal Correctional Institution in Sheridan. To a new start.

Only, prison wasn't exactly as comfortable as he'd imagined.

Admittedly naive, Homsley pictured the Big House the way it's often depicted on television: guy in a cell, reading a book. Free food. Strangely, he pictured it as safe. A refuge from the cold streets of downtown Portland. "No one is going to shoot me in there."

But it wasn't safe, and it especially wasn't safe for Waldo. Upon arriving at Sheridan, Homsley quickly discovered the penitentiary's pecking order: You either join a gang or you're the plaything of a gang, like the snitches or child molesters or rapists who can expect regular beatings at the hand of would-be gang members as a ticket to initiation.

And there's one more category: "famous" people. People like the Where's Waldo Bandit. Beat up Waldo — which is pretty easy to do — and it earns you chits. "It's your entry fee," he says. Not long after arriving at Sheridan, Homsley found himself a target.

Two other factors made Waldo's hard time even harder.

Problem One: He's got a mouth on him. Homsley may insist he wants to lie low and stay out of everybody's way, but the reality is he's got a lousy filter and rarely resists the urge to talk back, no matter who's hovering over him.

Problem Two: His fellow inmates figured out right away that Homsley knows how to draw. In prison, art is currency. He could draw templates for jail tattoos and he could draw pictures for dads to give their daughters when they come to visit. He could draw whatever you wanted him to draw; he could draw whatever you told him to draw.

"They'd assault me, make me draw and assault me again," he says.

So Sheridan was not the cushy Club Fed that Waldo had been promised. But after two and a half years, he was out and on his way to the halfway house, to get help finding work and to put his life back in order.

Only, that part of the plan didn't go as he'd hoped either. Ex-cons don't get to just pick whatever gig they think might suit them best. He successfully landed a job as a telemarketer, for example, but with his record, the Oregon Department of Corrections wouldn't allow him to take it. He couldn't work at a place where credit card information might be transmitted over the phone and pilfered by a criminal-minded customer service rep.

He could, though, work as a sign waver.

Waldo didn't like his options, and he wasn't quiet about it. He also violated the rules against using computers for anything other than looking for work. He checked his Facebook messages and emails, scanning through thousands of missives, mostly from strangers from all over the world.

"Stupid American robbing bank no masks," wrote one guy from Iran. "Next time wear mask dumb Waldo." He heard from ex-girlfriends, people he'd known in South Carolina. Someone wrote, "Kill yourself already."

After a few weeks at the halfway house, he was kicked out. When you're only out of prison because you're staying at a halfway house, it means you're still in Oregon's custody. If you're kicked out of the halfway house, you do not pass go or collect $200. You go back to prison.

So Homsley went back and finished the last few months of his sentence in prison. More getting pummeled so that someone else could gain entry to a gang, more beatings for art, more misery. After this round, though, he was free. He'd done his time.

Then came a new problem: He had nowhere to go. Corrections officials bused him in to Portland with a supply of insulin and a bag of needles, at which point he was supposed to report to a probation officer. With no friends and nowhere to stay, Homsley wound up at a homeless shelter.

He did know how to rob banks, though.

Waldo's second heist

If it seems hard to imagine why robbing another bank would even cross Homsley's mind at that point, understand a few things: If it wasn't already clear, he's a little self-destructive. He'd made up his mind that nothing was worse than another round of homelessness, where finding insulin is a constant struggle. At least in the pen, he could manage his diabetes. And he was desperate.

"I'm not doing homeless again," he says. "Three hots and a cot, if that's my only option, I'll do that."

This time, at least, police reports show that Waldo had learned some lessons. He had come up with a better plan.

On Aug. 26, 2013 – less than a week after his release from prison – he walked into the lobby of the U.S. Bank at Southwest Fourth Avenue and Harrison Street in downtown Portland, he wore not a striped sweater but a sport coat with a white button-up shirt. He fumbled in his pocket for the note, and told the teller, "If my head wasn't screwed on, I'd lose that, too," according to court records. The teller asked if she could help him, and he said, "You can help me with this," sliding over the note: "No sudden moves. No alarms (do not follow.) No one gets hurt. 100's 50's 20's 10's 5's. NO DYE-PACKS. BE COOL + no one gets hurt." He also drew a smiley face.

This time, no black box, no "boom."

"Is there a dye pack?" Homsley asked the teller. "No dye pack," she said. "Do you have a bag?" he asked. The teller got up to get Homsley a bag, and he stood there in the meantime, flipping through the money. He received $1,671 this time, walked out, caught a light rail train, scored another Hondo and partied for three more days.

An officer at the Multnomah County Jail recognized Waldo as soon as the robbery surveillance photos were released to the media and called Portland Police to pass along the tip.

Court records show that Homsley's undoing that time around was the dentist. He'd gone to Healthy Smiles Dental Group to "get some work done on his teeth" (and score some painkillers). He filled out the intake paperwork, checking the boxes for diabetes, jaundice, thyroid and liver disease and complained of bleeding gums, sensitivity, pain and frequent headaches and left, at which point an employee there who recognized him called police. By day's end, Portland Police found Homsley at an abandoned house, responding to a call about a "suspicious" person there. When the officer arrived, he found Homsley, shirtless and shoeless, claiming he'd paid $25 to stay there for a couple of nights. In a shed behind the house, the officer found Homsley's suit jacket and "quite a bit of money."

Waldo was in custody, with $647 from the bank robbery left.

Seasoned criminal

Ryan Homsley's arrest mugshots from October 2010 (left) and August 2013.

Homsley's second mugshot is starkly different from his first. His face is pudgier, evidence of the 40 pounds he'd gained since the first pinch in 2010. In the first picture, he looks wide-eyed and scared. In the second, he looks like a seasoned criminal.

This time, it wasn't his first offense. He pleaded guilty, and now, as he whiles away the hours in the Columbia County Jail awaiting sentencing on his second bank robbery, Homsley faces not a few months at Sheridan – but five years.

It would seem a completely hopeless situation, but for one guy: Matt Schindler.

Schindler is a big bear of an attorney with a big booming voice and a bigger personality, and he may be the only person on Earth who believes in Ryan Homsley.

Unlike the vast majority of Schindler's clients, Homsley is literate and intelligent, and he has a real talent: that artwork. He's not violent. His main obstacle is drug addiction. Drug addiction can be overcome.

"It's just insane to think about the investment involved in incarcerating somebody who's literate, intelligent and capable," Schindler says. "He needs rehab, not prison."

So Schindler is working years ahead, to the day Homsley is released, to find a judge willing to let him out with a better start this time.

"I will make sure there's stuff in place, so it's not a bottle of insulin, a bag of syringes and a wish," Schindler says. "That's just a bad plan for anybody."

Even from the inside, Homsley is working to improve his lot. The San Francisco State University literary journal "14Hills" plans to publish five piece of Waldo's art sometime in the near future, Schindler says. He's also working on a zine called "The Mad Parasite" with a Portland comic book writer named Billy McKay. The two met in 2011 after Homsley wrote McKay asking for zines and comics to read. In trade, Homsley sent his own original artwork.

"It was unusual to receive anything in trade from an inmate, and even more unusual for the art to be of such a high quality," says McKay, who fields requests from inmates regularly. After Googling, Waldo, "It was pretty clear that Ryan was not a violent offender, that he was a gifted artist under unfortunate circumstances, and that he could likely benefit from having a structured outlet for his art and writing."

Homsley now signs his sketches "Waldo." He calls himself that, too, in a maybe misguided attempt to come to grips with this dark chapter of his life.

"It's a nickname I've earned," he says from the other side of a small table in the jail conference room, his hands and feet shackled, his county-issue pants striped just like Waldo's sweater.

-- Winston Ross, a former national correspondent at Newsweek and The Daily Beast, is a freelance reporter. His work can be found at winstonross.wordpress.com.