Jack Rosga: Outlaws gang leader or ‘working stiff'?

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MCs in the News

Federal allegations clash with low-key image

By Ryan Haggerty This e-mail address is being protected from spambots. You need JavaScript enabled to view it and John Diedrich This e-mail address is being protected from spambots. You need JavaScript enabled to view it of the Journal Sentinel

Jack Rosga kept a low profile for a man who federal authorities say was the national leader of the Outlaws Motorcycle Club, ordering subordinates to attack rival gang members while living and working in Milwaukee.

Known as "Milwaukee Jack" within the club, Rosga, 53, has a relatively clean record. A lawyer representing him says Rosga is a "working stiff" who runs a small trucking company, doesn't smoke and has an occasional sip of Crown Royal.

But both Rosga and the Outlaws, a group that works to maintain a positive public image, are portrayed in a far different light in a 12-count indictment filed last week against Rosga and 26 other Outlaws from seven states.

The indictment includes accusations of attempted murder, kidnapping, assault, robbery, extortion, witness intimidation, drug dealing, illegal gambling and gun charges, much of which Rosga allegedly directed from Milwaukee.

Rosga told an undercover agent he expected to one day end up in jail, following the Outlaws' two previous national leaders, both of whom are in federal prison, the indictment says. Rosga also told undercover federal agents posing as Outlaws that they should shoot members of the rival Hells Angels gang, according to the indictment.

Rosga's arrest last week during a surprise raid at the Outlaws' clubhouse on Milwaukee's south side is the latest chapter of the club's history in the area, which stretches back decades and includes previous federal investigations, battles with rival gangs, bombings and at least seven unsolved homicides, according to court records, law enforcement officials and news accounts.
Milwaukee ties

The Outlaws trace their roots to 1935, to a bar on Route 66 near Chicago. Their motto: "God forgives, Outlaws don't."

In 1964, Milwaukee bikers formed an Outlaws chapter. It was the first outside Chicago, and Milwaukee has since remained a stronghold of the gang.

The Outlaws operate like a corporation, with local chapters, regional officers and a national leader, according to law enforcement officers who have investigated the club. Members pay monthly dues, and the gang exacts taxes from members for special expenses, such as funeral costs for members, according to court documents and experts.

The gang also funds itself through illicit operations, including drug dealing, fencing stolen cars and motorcycles, gambling and counterfeiting money, according to law enforcement officers who have investigated biker gangs.

The Outlaws are closely knit, and it takes months of vetting and testing before a prospect is allowed full membership as a "one-percenter." The term comes from a declaration by a motorcycle club in the 1940s that 99% of riders are law-abiding citizens. The Outlaws declare they are not among that group.

For years, the group passed with little notice in Milwaukee, but in the 1970s, law enforcement officers in Milwaukee pursued the Outlaws, mostly for stolen car rings and beatings of rival biker gang members.

Investigations took a more serious turn in 1974, when Milwaukee Sentinel carrier Larry Anstett, 15, was killed while delivering papers when he picked up a bomb disguised as a present. The bomb was on a car owned by a member of a rival motorcycle gang who had testified against the Outlaws.

It remains one of the most notorious homicides in Milwaukee history.

Six homicides in the Milwaukee area followed Anstett's murder. All the victims - both Outlaws and people outside the gang - may have had knowledge of who placed the bomb, according to local authorities.

Those killings include the 1987 murder of Michael Drobac, who along with his wife and son were found shot to death in their Washington County home.

None of the homicides, including Anstett's murder, has been solved.
'A violent group'

Federal authorities cracked down hard on Outlaws with ties to Milwaukee in 1997 and again in 2001. A total of 23 gang members were convicted and were sentenced to prison for a string of murders, bombings, arsons and drug dealing as a result of the two cases. Five of them got life terms.

The most shocking crime linked to Outlaws with ties to Milwaukee was the 1993 execution of an elderly couple, Ruth and Morrie Gauger, and the robbery of their motorcycle shop in McHenry County, Ill., according to court documents. There were also attacks on rival gangs, especially the Hells Angels, who were making incursions into Wisconsin, territory long held by the Outlaws.

"They were a violent group," said Assistant U.S. Attorney Carol Kraft, who handled the Outlaws cases and spoke about the group she prosecuted.

"Their whole goal and all their energy was directed toward maintaining control over areas. The evidence showed they were willing to go to any and all lengths to make that happen."

Nine members of the Outlaws went on trial in the first case, but authorities were able to get only one member of the gang to testify.

Jack Rosga didn't surface in either of the earlier Outlaw prosecutions, Kraft said. But authorities say he was on the rise in the group and became the club's leader in 2006.
Their best face forward

Public defender Chip Burke, who represented Rosga during his court hearing last week, said Rosga is a regular guy who has worked in the moving business for 30 years. Most recently, Rosga ran a company of his own with 14 trucks he leased to big moving companies, Burke said.

Rosga's company was called Rosga Trucking, according to online directories.

"He had been real successful in his work," Burke said, adding Rosga told him he made $100,000 last year. "A guy like that presents a good face for this group."

Burke said Rosga has a criminal conviction from the 1970s, but no court records for the case could be found. Rosga also was arrested in 1996 for violating a restraining order obtained by his wife, who accused him of taking her credit cards and hitting her, according to court and jail records.

Rosga's limited criminal history and his ownership of the trucking company probably helped him become the Outlaws' national leader, said Steve Cook, a police detective in suburban Kansas City who has been involved in investigations of motorcycle gangs for more than 16 years.

"I definitely think (a candidate's criminal record) is something that they take note of when they're doing their selection," Cook said of the Outlaws. "Who's got legitimate income? Who at least has the appearance of being a businessman? Who doesn't have a lot of criminal (convictions)?

"Obviously, it's not going to be real attractive for them to pick somebody who has several violent felony convictions or drug convictions or things like that, because that's going to give law enforcement something to (focus on) at the get-go."

Rosga was estranged from his wife, Lydia, when she died in 2003 after overdosing on prescription drugs, according to a Milwaukee County medical examiner's report.

Jack and Lydia Rosga had at least two children, Joseph and Jack Jr., according to court records.

Jack Rosga Jr., 31, was convicted of nine burglary counts in three separate cases in 2005 and 2006 and is in custody at a state prison in New Lisbon, according to court and prison records.

Rosga wrote a letter to a Milwaukee County judge before his son was sentenced, pleading for leniency.

"Jack spent years working with me, side by side," Rosga wrote. "I have been in the moving business all my life. He was one of the hardest workers of all my employees. He never quit before the job was finished."
Conflicting accounts

Rosga did not keep his Outlaws membership a secret. In fact, Rosga and other local Outlaws have filed lawsuits accusing Milwaukee police of harassing them.

In August 2003, three members of the club filed a civil rights suit against Milwaukee police and Summerfest, saying their rights were violated when they were booted from the festival for refusing to take off or cover their patches.

The Outlaws later dropped the case, but in 2007 they were back in federal court, filing another civil rights lawsuit against the city and Police Department.

One of the plaintiffs was Rosga.

On Sept. 25, 2006, Milwaukee police said officers spotted Rosga and two other men on the roof of the clubhouse with a long gun, according to Milwaukee Assistant City Attorney Sue Lappen. Officers were dispatched and were allowed in the clubhouse by a member, she said. They found a long gun but made no arrests, she said.

The Outlaws' lawsuit gave a different version.

It said Rosga and the others were on the roof checking for leaks. They said 19 officers rushed into the clubhouse without a warrant, shoving guns in their faces.

The suit contended police violated the Outlaws' rights and said police constantly harassed Outlaws members by pulling them over for minor violations.

Rosga and the others claimed "mental anguish, anxiety, emotional distress, loss of enjoyment of life and other financial losses."

Lappen said because they were claiming financial losses, though no amount was specified, she sought tax returns for Rosga and the others. They refused to turn over the documents, and that is where the case ended, she said. The city paid no money but agreed the clubhouse would be treated like any business - meaning officers would contact the owner if a non-emergency situation was reported, such as graffiti, Lappen said.

"It wasn't really a concession. We said we will treat you like any other small business owner, but if there are exigent circumstances, we are going to come in," Lappen said, adding if officers saw someone on the roof with a gun, she would expect officers to respond without calling the owner.

Todd Korb, who represented the Outlaws during their lawsuit about the clubhouse search, said the case came down to one person's word against another's on the search. He said the city's demand for tax returns wasn't the reason for the settlement.

"We amicably resolved it. We had an understanding that we would have better communication with police in the future," Korb said.

Several Outlaws declined to answer a reporter's questions Tuesday as they watched federal agents remove boxes of evidence from their clubhouse.

The only Outlaw to attend Rosga's court hearing later that day also declined to speak with a reporter, saying, "You know we don't talk."
Outlaws' territory

Although none of the attacks included in the indictment occurred in Milwaukee, authorities accuse Rosga of directing some of the violence from Milwaukee.

If convicted he faces up to 23 years in prison. He is expected to be tried in Virginia.

He gave the "green light" to retaliate after an Outlaws member was fatally shot outside a strip club in Georgia in 2007, according to the indictment. He also told a fellow Outlaw to clean his own house, meaning anyone suspected of helping law enforcement should be killed, the indictment says.

Last July, Rosga told undercover agents posing as Outlaws that they should shoot Hells Angels members, according to the indictment. And in October, Rosga demanded revenge on the Hells Angels after two Outlaws were attacked at a Florida gas station. Four days later, a Hells Angels member in Maine was shot by an Outlaw but survived.

Violence between biker gangs flares up when one club tries to move in on another. That might explain why there haven't been violent flare-ups in Milwaukee, according to experts. The city is solidly Outlaws' turf.

"In many ways, Milwaukee should be happy, not necessarily that they have the Outlaws, but that they have no rival gangs," said Terry Katz, a retired Maryland state trooper who has infiltrated biker gangs and is vice president of the International Outlaw Motorcycle Gang Investigators Association. "But if tomorrow the Hells Angels came in, you would within a very short period of time have violence."

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