It was an act of desperation, really.

At the time of the robbery, Mike "Libretto" Jackson had been out of work for a year and a half. His unemployment checks were running out, and whatever money he was earning as one of Portland's most prominent rappers wasn't enough for him to continue keeping the lights on, or providing for his family. When an acquaintance called him to visit New York, the original idea was to run some guns up from South Carolina to sell on the black market. Then a more lucrative opportunity came through. Jackson is cagey about the details, but it involved a heist on an immigrant-owned business operating as a front to wire cash back to Africa.

Growing up in Watts, Jackson committed his share of misdeeds, petty theft and the like, but the way he looks at it, he just did what he had to do to survive in one of L.A.'s roughest neighborhoods. As he puts it, "People call it gangbanging, I call it maintaining."

In the midst of the recession, with his back against a financial wall, he decided to maintain.

It ended up landing him in federal prison for 4½ years. And if he ever runs into the judge who sentenced him, Jackson promises things will get physical.

"I'm going to hug him and say, 'Thank you for giving me that time,'" he says from a couch at the back of the Rosewood Initiative community space in East Portland, where he works part-time, "because that time made me a whole new man."

Gratitude isn't what you'd expect from someone only a few months out of an ankle bracelet. But to hear Jackson tell it, incarceration was like an extended self-improvement workshop. He read voraciously. He studied business. He paid another inmate to teach him piano with bags of coffee. He changed his diet and got into the best shape of his life—if he decided to play wide receiver in the NFL, he could get an invite to training camp on his physique alone. And he wrote—pages upon pages of lyrics, a small sampling of which forms the basis of his first post-release project, Gangsta Jazz Vol. II. It wasn't a spa retreat, of course—it took him away from his kids, stalled his career and left him with personal-space issues he's still trying to shake off—but overall, the experience was a net positive.

"I don't wish prison on no man," he says. "But at the same time, there's an ancient Chinese proverb that says you're not a real man until you experience time in exile. That sat with me in there, because I learned a lot of discipline. It really made me a better person in the long run."

For Jackson, the hard part really starts now. In the early aughts, the rapper known as Libretto was among the best-known MCs in the city. Armed with a calmly authoritative baritone and an outsider's perspective—his father moved the family out of Los Angeles and into the shocking quiet of Milwaukie in the mid-'90s—his mix of street-poet brains and gangsta brawn placed him on a tier with respected vets like Cool Nutz, Mic Crenshaw and his Misfit Massive crewmates, the Lifesavas. His debut album, 2004's Ill-Oet: The Last Element, was the first rap record released on Dim Mak, the punk-and-dance label started by future megabucks DJ Steve Aoki, and it drew enough underground acclaim for Jackson to tour outside the Pacific Northwest.

But in the fast-moving world of hip-hop, losing five years might as well be a generation, if not two or three; the scene in Portland alone has turned over several times since Jackson went in to do his bid. He accepts that re-establishing himself in the rap game means ceding headliner status to emerging artists, some many years his junior. But that doesn't mean he's always happy about it.

Once again, Jackson finds himself in a position of figuring out how to maintain. As noted, though, his instincts for self-preservation are well-honed. He was forced to begin sharpening them at a young age. His parents divorced when he was 5 years old, and his mother went on the road leading religious revivals; she died when he was a teenager. And while his father, a former Black Panther and track coach, did what he could, work often forced him to leave the country for months at a time.

Jackson spent his childhood in a constant state of eviction, going from house to house, sometimes living out of the family station wagon. "It was a daily struggle," he says. His life didn't stabilize until high school, when his dad retired and, at the urging of his older sister, relocated Jackson and his brother to Portland. And even then, he spent his first year sequestered in Milwaukie, never visiting the city proper, and using the Social Security checks from his mother's death to fly back to L.A. every weekend, "because that's just home," he says.

At that point, Jackson had already been rapping for a number of years. He started as a preteen, climbing into the DJ booth at local skating rinks and commandeering the microphone for spontaneous freestyle sessions. But it wasn't something he thought he could make his name doing until he finally ventured to St. Johns and fell in with the then-ascendant Lifesavas.

Onstage, Jackson's imposing presence stood out among his more convivial peers. "People seen I wasn't from here," he says. "I rapped different, but my swag was more gangsta. I was more gangbanging, because I was still kind of banging back then, but I was turned down because I wasn't in L.A."

After a few introductory singles, Ill-Oet arrived in late 2004, showcasing the black consciousness learned from his activist father and the street knowledge drawn from his own upbringing. Local media declared him Portland's potential next big thing.

And then, in 2008, he lost his nonprofit job.

In the intervening years, Jackson worked on several projects, only a handful of which have been released. Completed in quick-and-dirty fashion while Jackson transitioned back to freedom in a halfway house, Gangsta Jazz Vol. II—an album-length sequel to a previous EP put out through Portland's Liquid Beat Records—isn't the formal follow-up to Ill-Oet, but it's a poignant reintroduction regardless. Over crackling jazz samples, Jackson reflects on his past ("All That Jazz") and his imprisonment ("Black Codes") while accepting whatever's next with Zen-like calm. "Once I exited that prison complex/I suspect the streets won't embrace me," he raps on the dreamy closer, "So Good." "It's like I never left, so why stress?"

Now that he's out of prison, Jackson is trying to make up for lost time. He's hoping to find a home for some of the records he finished before going away, the most crucial being Captain Crook, his official sophomore LP many years (and a lot of money) in the making. As he edges up against 40, and with the state of the music industry being what it is, Jackson knows the clock is ticking: He doesn't expect to still be rapping three years from now. But as he says, he's not stressing. Because if prison taught him anything, it's to be satisfied with what he's got right now.

"You learn to be happy sitting in traffic with nothing," he says. "You've got freedom, you've got life. Everything else is secondary."

SEE IT: Libretto plays Mic Check at White Eagle Saloon, 836 N Russell St., with the Last Artful Dodgr, on Thursday, Sept. 29. 10 pm. $5 advance, $7 day of show. 21+.