Hopeful signs: Rob expects to double his freelance income this year; Shannon just landed a part-time nanny job that will leave plenty of time for Ryan.

The bottom line The Rothbergs are determined to pay back the money lent to them by family and friends. Next up: saving to buy a house. Income Rob's freelance jobs (estimated) $70,000 Shannon's income $4,400 TOTAL $74,400 Outgo 2005 taxes (estimated) $15,000 Rent $13,680 Health insurance $11,400 Transportation (car maintenance, gas, bus fare) $7,800 Food $5,200 Car payments $4,800 Utilities $4,800 Entertainment $2,600 Car insurance $2,400 Clothing $1,800 Roth IRA contributions $1,660 2004 back taxes $1,460 Gifts $1,200 Student loans $600 TOTAL $74,400 Assets Rob's 1991 Acura NSX $20,000 Roth IRA $5,660 TOTAL $25,660 Liabilities Debts to family and friends $36,000 Shannon's car loan (2002 Toyota RAV4) $16,000 Student loans $2,000 TOTAL $54,000 Net worth -$28,340

NEW YORK (MONEY Magazine) - Rob Rothberg had it made. At age 32, he was a fast-track high-tech manager leading a team of software developers at NEC Corp. and earning a solid $115,000 a year. He tooled around Boston in a sleek Acura NSX sports car and had just begun dating a pretty blonde named Shannon.

The good life turned out to be short-lived. On a cold February morning in 2000, as Rothberg and his girlfriend lay in bed, federal agents arrived at his townhouse with badges flashing, arrested him for software piracy and hauled him away in handcuffs.

No one was more shocked than Rothberg, a shy, soft-spoken computer wiz who, for fun, often swapped bootlegged copies of software with friends and colleagues but never sold the programs for a profit. In Rothberg's mind, his activities were no more criminal than the song swapping that millions of music fans engaged in on the old Napster.

The FBI didn't see it that way. The Justice Department held a press conference announcing the capture of Rob Rothberg, a.k.a. "Marlenus," ringleader of a nefarious online group called Pirates with Attitudes. The charge: conspiracy to commit copyright infringement, a felony punishable by up to five years in prison.

"What I did was wrong," Rothberg admits, "but I thought of it like speeding was wrong. I'd maybe get a slap on the wrist and pay a fine."

Rothberg wasn't the only one to believe the punishment he faced didn't fit his crime. Commenting on the case at the time, Marci Hamilton, a copyright scholar at the Benjamin N. Cardozo School of Law, said, "The penalty is completely disproportionate to harm caused."

Rothberg initially fought the charges, but after more than two years of legal wrangling and mounting bills, he decided to plead guilty, serving a 15-month sentence.

For every Martha Stewart, Dennis Kozlowski or other high-profile white-collar criminal whose wealth and fame cushion a fall from grace, there are countless more like Rothberg, who left prison in December 2003 broke, jobless and deeply in debt.

Since then he's managed to find freelance work and he has made $35,000 so far this year. But with his ex-con status hanging over him like a scarlet letter, a job close to his former status seems completely out of reach. He wakes up every day to a question he never dreamed he'd be facing back when he was a golden boy in the IT world: How does a man recover from a single colossal mistake that has turned his life into a nightmare?

The silky black hair that spills over his shoulders may have helped the prosecution paint Rob Rothberg as a dangerous outlaw. But sitting in the cramped four-room apartment he shares with Shannon, who married him two weeks before he began serving time, and their baby Ryan, seven months, he seems more like the naive computer geek who lived at home until he was 26 and used to stay up all night chatting online.

For Rothberg, the virtual world offered a kind of camaraderie that he rarely found offline, particularly when he was wowing online buddies with his skill at reverse engineering software he found on bulletin boards.

In 1994, Rothberg discovered Pirates with Attitudes, an online community of techies who maintained a vast library of software -- including programs for operating systems, data analysis and games -- that members could download and play around with.

Rothberg's technical skills enabled him to quickly move up the group's hierarchy. With access to thousands of programs, he reveled in being the go-to guy at the large bank in Boston where he was then working.

"I can't count how many times my boss or a co-worker said, 'You saved the day with that software,'" he recalls.

In 1997, Congress made it a criminal offense to download copyrighted software, even if the perpetrator didn't personally profit. But Rothberg continued to rationalize his activities. After all, his employer usually bought the programs after trying out the bootlegged version, so he was actually helping the software companies generate sales! Besides, what was the worst that could happen? A cease-and-desist letter? If so, he'd simply stop.

Bad call. Rothberg and 16 others were nailed in an FBI sting operation billed as the largest case of its kind at that time. He hired a top lawyer at $420 an hour, which his father, a minimum-wage worker at a golf course in Florida, helped pay by lending him his life savings of $11,000.

"It meant a lot to me that he did that," Rothberg says, "and it's very important to me that I pay him back."

His job situation was also unraveling. Rothberg, who had left the bank to work for NEC, was laid off after a corporate reshuffle shortly before his arrest; though he eventually found a new IT job, the legal bills grew so quickly that he was forced to liquidate his 401(k) and other investments to raise money, some $75,000.

"It was a very difficult, depressing time," he says. "I was lethargic at work, I put on weight, and I went to see a shrink."

The only bright spot was Shannon, now 38, who stuck with him the whole way. "I tried to keep my thoughts about what was happening legally separate from how I felt about Rob and just move forward with the relationship," she says. In November 2001, Rothberg asked her to marry him and she said yes.

Otherwise, though, reality was grim. His new employer went out of business, and a subsequent consulting gig dried up when it became clear that he was headed for jail. The case dragged on and the legal fees kept climbing, eventually reaching $250,000.

Rothberg decided enough was enough. He changed his plea to guilty and received 18 months in prison (although he was released after 15 for good behavior).

While Rothberg was locked up, Shannon made ends meet working as a nanny for $35,000 a year and trying to generate donations on a Web site, Freerobrothberg.com. But her efforts raised only $800 -- not nearly enough to cover their remaining $100,000 in legal bills and $25,000 in back taxes.

When Rothberg was finally released from prison, he found that he'd become a pariah in the technology industry.

A typical scenario, according to Rothberg: Dell flew him to Austin for an interview for a high-level tech job that went well until he told them of his conviction (as the terms of his probation require him to do). Soon after, he received a call saying he just wasn't a good fit.

All told, he's sent out well over a hundred resumes. But he's learned that competing successfully with hundreds of applicants is next to impossible with a felony on your resume.

Rothberg has gotten by with consulting work, earning about $33,000 last year. Shannon added another $18,000 as a nanny. But there was no money left after living expenses to pay off his debts. Last November, Rothberg filed for bankruptcy, erasing most debts to creditors, although he still owes $36,000 to friends and family.

The irony of his situation is not lost on him. Before his arrest, he made lots of money and had few responsibilities. Now it's the other way around.

"I want the same things everybody else wants," says Rothberg, now 38 and keenly aware that middle age is just over the horizon. "I want a house with a mortgage I can afford and money left over to save for the future."

Next: Our career rehabilitation experts' advice for Rothberg.

_____________________

Click here for our special report, "Your Job 2005."