(These are super rough, broad outlines. For a book on the Milwaukee Outlaws, see Michael Grogan’s “You Gotta Be Dirty.” I personally think another book or two could be written on the Milwaukee Outlaws in addition to Grogan’s work. I won’t do it, but if anyone wants a research assistant, let me know.)
1935: The McCook Outlaws are established at Matilda’s Bar on Route 66 in McCook, Illinois.
July 4, 1964: Milwaukee’s “Gipsy Outlaws” join the organization, establishing a stronghold in Wisconsin. Founders were brothers James, John and Joseph Bisenius of West Allis. They were involved in sexual assault and protested helmet laws.
March 1, 1970: A party in Sheboygan, to see if the Untouchables MC could join the Outlaws, devolved into a stabbing. 19-year-old John Werner was killed.
June 28, 1972: Victoria Horneck, wife of Untouchables president, was shot multiple times and quickly buried in rural Sheboygan.
In 1974, Larry Anstett, a 15-year-old paperboy, is killed in Milwaukee after picking up a bomb disguised as a Christmas gift. The device was intended for the president of the rival “Heaven’s Devils” gang. Throughout that year, shotgun blasts and other violence targeted the Devils, especially Michael Vermilyea.
On September 30, 1977, three members of the Outlaws – Michael “Sledge” Goodman, Roger “Rocker” Lyons and “Horrible” Harry Ross – were involved in a bar brawl with three men who were playing pool at the Bus Stop Tavern on Milwaukee’s northwest side. After police were called, twelve officers arrived and evicted five of the men from the premises. Lyons refused to leave until he was allowed to finish his drink, and he was restrained and handcuffed. Lyons was then beaten unconscious by police with batons and placed in a police van. He was first taken to District No. 7 station house and subsequently pronounced dead on arrival at Milwaukee County Hospital. A medical examiner’s inquest ruled that Lyons’ death was “the result of brain swelling and concussion due to multiple blunt trauma injuries” and concluded that the “manner of death was the unlawful homicide by reckless conduct caused by a person or persons undetermined”. A coroner’s inquest and a federal grand jury found no evidence to justify prosecution of the Milwaukee Police Department.
According to a 1980 DEA report, the Milwaukee chapter controlled the methamphetamine market in Wisconsin.
In the early morning hours of November 29, 1980, Milwaukee police officer Eugene Grabowski responded to a complaint at a Milwaukee tavern. The tavern owner told Grabowski that there had been a fight between two customers resulting in glass being thrown and shots being fired into the jukebox and ceiling. The owner recognized one of the suspects as a member of the Outlaws, who was later identified as Edward Anastas.
Later that day Grabowski was contacted by Sergeant Eric Slamka of the South Milwaukee Police Department. Slamka said Anastas was in another bar, this one in South Milwaukee, along with other members of the Outlaws. Grabowski and other Milwaukee police officers met with Slamka several blocks from the South Milwaukee bar to discuss plans for entering it to arrest Anastas. The group of officers entered the bar through its only two doors, some of them carrying shotguns. Douglas Paul Mattes was one of five patrons in the bar, and he was wearing a cap with an Outlaws emblem. Grabowski saw Mattes stand up, look away from Grabowski, and move his hand to the area near his waist. Grabowski ordered all the patrons to put their hands on the bar and they complied. All the patrons, including Mattes, were frisked. Mattes is 6’5″ tall and weighs 320 pounds. Grabowski found a loaded .38 caliber pistol in Mattes’s pocket. Mattes was indicted on January 27, 1981, was tried before a jury and was convicted on October 14, 1981. The court imposed a sentence of one year and one day in prison.
1987: Michael Drobac, along with his wife, are found shot to death in their Washington County home.
In 1992, around forty members of the Outlaws crashed a party being held by Milwaukee-based Sinners Motorcycle Club and began pressuring the Sinners to wear an “A.O.A.” patch on their vests to show allegiance to the Outlaws. The Sinners refused to capitulate to the Outlaws’ demands, leading to a confrontation at the Sinners’ clubhouse at which Sinner Charles “Peewee” Goldsmith was stabbed in the back with a screwdriver. The Sinners disbanded after only six of the club’s 26 members voted to go to war with the Outlaws, the other twenty handing in their patches. Goldsmith fled Milwaukee and joined the Hells Angels.
On August 24, 1992, Donald Wagner was killed by the Outlaws in Racine County.
1993: Ruth and Morris Gauger, an elderly couple, are executed during a robbery of their motorcycle shop in McHenry County, Illinois. Their killer was Outlaw “Madman” Miller.
Ahead of a Pro Stock Motorcycle drag race in Milwaukee in June 1993 at which Patrick Matter, the president of the Minneapolis Hells Angels, was expected to compete in full Hells Angels colors, Outlaws leader “Taco” Bowman led 25-30 Outlaws in confronting Matter. Bowman took offence to Hells Angels wearing their vests in Milwaukee, a city considered Outlaws territory and arrived at Matter’s motel with a MAC-10 submachine gun, leading to an armed standoff with a group of Angels who were on the second floor of the motel. The Outlaws warned Matter if he took part in the race while wearing his Hells Angels patch, he would “have a problem”. Matter refused to acquiesce to the Outlaws’ demands but later reconsidered on the advice of East Coast Hells Angels president Kevin Cleary.
In late 1993, Outlaws leaders suspected the Hells Angels were attempting to gain a presence in the Chicago area by “patching over” the Hell’s Henchmen, a biker gang with chapters in Chicago, Rockford, Calumet City, and South Bend, Indiana. Initially a small club consisting of approximately twenty members, the Hell’s Henchmen had co-existed with the Outlaws without violence as they showed no ambitions to expand. The Outlaws became alarmed, however, when the Hell’s Henchmen carried out a forced amalgamation of the Devil’s Ushers gang on the West Side of Chicago. When the Outlaws attempted to coerce the Hell’s Henchmen into “patching over”, the Henchmen held a meeting with the Hells Angels in Indiana and agreed to “prospect” for the Angels instead.
Pat Matter was the orchestrator of the Hells Angels’ expansion into Illinois and Indiana. Bowman ordered Matter’s assassination, and a hit squad consisting of James “Preacher” Schneider, Scott “Rhino” Hammond and Randall “Madman” Miller of the Outlaws’ Milwaukee and Janesville chapters traveled to Minnesota to carry out surveillance on Matter ahead of a planned execution after they were provided with money, a weapon, and surveillance notes by Milwaukee president Edward “Shock” Anastas. The Outlaws were unsuccessful in carrying out the killing, however, because the hit team never “got a shot at” Matter. Several months later, on December 15, 1993, Outlaws members attempted a car bomb attack on Matter outside his business, Minneapolis Custom Cycle. The attempt failed when the C-4 bomb detonated prematurely, destroying Matter’s truck and injuring the biker who planted the explosive.
At a meeting at Bowman’s residence in Detroit in September 1994, Bowman gave permission to Chicago Outlaw Carl “Jammin’ Jay” Warneke and Gary member Randy Yager to bomb the Hell’s Henchmen clubhouse. At 6 pm on November 7, 1994, Kevin O’Neill, the president of the chapter in Janesville, and Gary chapter president Raymond “Shemp” Morgan detonated a 100lb C-4 car bomb in a 1989 Ford Taurus sedan outside the building, located at 1734 West Grand Avenue. No casualties were reported, although a steel door to the clubhouse was damaged and windows on a number of buildings and parked cars in the area were shattered. The attack was the second-largest car bombing in United States history at the time, surpassed only by the 1993 World Trade Center bombing.
On June 10, 1997, U.S. Attorney Thomas Schneider announced the indictments of 17 Outlaws members on federal racketeering charges related to crimes committed by the gang between 1988 and 1997, including arsons, bombings, robberies, six murders and five attempted murders. Twelve of those indicted were members of the chapter in Janesville, two were members of the South Side, Chicago chapter, another two were members of the Gary, Indiana chapter, and the other was a member of the La Crosse chapter. The indictments primarily stemmed from the Outlaws’ war against the Hells Angels and followed a four-year investigation by the ATF. The ATF’s investigation of the Outlaws was aided by testimony from two former members, Mark “Crash” Quinn and Harry “Lord of Laziness” Raymond. Quinn had turned state’s evidence when his parole was revoked and he was returned to a Wisconsin state prison on a battery and intimidation conviction after being arrested by the Illinois State Police in March 1994.
Six Outlaws members from Wisconsin and Illinois were indicted in the Eastern District of Wisconsin on June 7, 2001 on federal racketeering and drug conspiracy charges. The indictments followed a two-year investigation by the federal ATF along with state and local law enforcement agencies. Five of the bikers – Edward Anastas, Ronald Talmadge, Thomas Sienkowski, Scott Hammond and Gregory Mayer – were arrested during a series of coordinated raids, while the other, Orville Cochran, remained at large. The indictment charged that the Outlaws were responsible for drug trafficking and numerous incidents related to the gang war with the Hells Angels, including bombings and the murders of Hells Angels members Michael Quale, in Lancaster, New York in September 1994, and Jack Castle, in Chicago in March 1995. Facing the possibility of life imprisonment, Talmadge, a member of the Joliet chapter and former regional president, turned state’s evidence.
2006: Jack “Milwaukee Jack” Rosga officially becomes the National President of the Outlaws.
October 2009: Following Rosga’s alleged “green light” for retaliation, Outlaw Thomas “Tomcat” Mayne shoots a Hells Angels member in Canaan, Maine; the victim survived.
On June 15, 2010, the ATF arrested 27 members and associates of the Outlaws during a series of raids carried out in seven U.S. states, including Wisconsin.[162][163] Outlaws international president “Milwaukee” Jack Rosga was among those taken into custody.
April 8, 2011: Jack Rosga is sentenced to 20 years in federal prison for racketeering and conspiracy to commit violence.
May 2026: Jack Rosga is released from a Florida halfway house and reportedly prepares to return to Wisconsin to reclaim leadership of the club.