The beginning of the end for dynamic Outlaws Motorcycle Club boss Harry (Taco) Bowman came 20 years ago this week, in August 1997, via a federal racketeering and murder indictment out of Tampa, Florida. Bowman, today 67 and serving a life prison sentence, went on the run from the law for the next 22 months, before being apprehended in a club safe house located near Detroit. Outside of Hells Angels MC founder Ralph (Sonny) Barger on the west coast, Taco Bowman is probably America’s most well-known biker boss of all-time, a legend in Midwest underworld circles who reigned as the Outlaws International President from the early 1980s until just before the dawning of the New Millennium. Finally brought into custody in the summer of 1999 on a tip to authorities provided from one of his girlfriends, Bowman built a reputation equally formidable in lethality, leadership and ingenuity. In the years prior to his indictment, he had amped up the Outlaws’ longstanding war with Barger’s Hells Angels and even issued a murder contract on the head of Barger himself. Born in Marysville, Michigan, Bowman moved to Detroit in the early 1970s and soon joined the fast-growing Outlaws Nation. By the end of the decade, he had risen to the post of International Vice President under his mentor, Harold (Stairway Harry) Henderson, based in Dayton, Ohio and the first Outlaws leader to plant a flag outside of the country for the club which now boasts chapters around the world. When Henderson stepped down from being the club’s president in 1984 to deal with his legal problems, Bowman took his place. Earning his nickname due to his dark complexion and resemblance to being of Latino heritage, Bowman was an underworld rarity – he was both loved and feared. Behind his hypnotic leadership ability, the Outlaws swelled to record numbers with a national roster of more than 1,500 full-patch members and over 200 total chapters across the globe. The chameleon-like Bowman has been credited by law enforcement as being the first “businessman biker boss,” a trendsetter in pioneering the Outlaws foray into more diverse rackets and more sophisticated business ventures than just owning bars, strip clubs and tattoo parlors. He expanded his powerbase by forging sturdy ties with other crime syndicates, like the Italian mafia, Eastern-European gangs and high-standing members of legitimate society, such as wealthy philanthropists, politicians. judges and policemen. Known to dress and act for whatever company he was in the presence off, Bowman could be seen in his club colors and cut, rousing it up with the boys in a dust-stained bar one hour and the next be clean shaven, neatly-coiffed and decked out in a $5,000 suit, looking like he was ready to attend a board of directors meeting. He lived in a large red-brick house in the upscale suburban neighborhood of Grosse Pointe Farms and enrolled his children in a pricey private school nearby. He could be often seen around town being driven to appointments in a custom-made, bullet-proofed Cadillac, always accompanied by a pair of bodyguards. Unlike most of his biker brethren, he seldom wore his hair extra long, nor sported a heavy beard or bared a body filled with tattoos. “Taco was interesting because he kind of went against the grain and kept one foot in the straight world and the other in the biker world, while most of those guys want to stay as far away from the two-car garage and picket fence thing as possible” said one retired ATF agent. “The guy used to drive his kids to school and was active in neighborhood type stuff. He might have wanted to blend in more than usual, but make no mistake about it, he was a pretty ruthless individual who definitely raised a lot of hell in his time.” Immediately stamping his personal imprint on the organization, Bowman moved the club’s international headquarters from Chicago to Detroit. Then he is alleged to have ordered the execution of a Chicago-based Outlaws member in the days following the move as a means of sending a message that his regime would be a hellish and bloody one. And boy was it. Using a fortified clubhouse on Warren Ave, a high mile east of the Southfield Freeway, as his command center, Bowman, made a big splash right off the bat conquering the hearts and minds of his minions with his garish and gung-ho leadership style. In his next major decision, he tapped Wayne (Joe Black) Hicks, a Toledo-based Outlaw and a man with a vicious reputation as a psychopathic killer, to be president of the club’s integral Ft. Lauderdale chapter. Having a stronghold in Florida is imperative for any biker club’s success on a nationwide-level, since the state acts as a hub for biker culture in the south and portions of the east coast in general. Hicks, a gruffer, more physically-imposing version of Bowman, became Bowman’s most-trusted lieutenant and quickly gained the reputation as the overlord of biker activity in Florida. With the aid of the state’s regional president, William (Wild Bill) Pilgrim and his own personal bodyguard and top lieutenant Stephen (DK) Lemunyon, Hicks ruled the Sunshine State with a heavy hand. The rest of the decade was relatively tame compared to what was on the horizon for the future. Taco Bowman’s diabolical reign hit its stride in the 1990s, when the strapping and handsome biker czar upped the ante in his battle with enemies both foreign and domestic. Taco was on the warpath and his bloodlust had few limits. During the early part of 1991, Bowman ordered the murder of Raymond (Bear) Chaffin, a former Outlaws member in Florida who had left the gang and re-affiliated with the Warlocks, a rival biker club backed by the Hell’s Angels. He gave the contract to Hicks, who in turn had club enforcers Houston (Part-Time Tex) Murphy and Alex (Dirt) Ankerich shoot Chafin to death on February 21. A little over a year later in March of 1992, Bowman oversaw and directed the physical beating of an Outlaws probate member named Irwin (Hitler) Nissen down at Biker Week in Daytona Beach. Nissen was being punished for getting into a physical altercation with Atlanta Outlaws chapter president, James (Moose) McClean the previous afternoon at a wet t-shirt contest held at an Outlaws-owned bar. Brought to Bowman’s hotel room, Nissen is beaten, threatened with a knife, and then thrown over the balcony by Bowman and fellow Outlaws members, Part Time Tex Murphy, Dennis (Dog) Hall and Christopher(Slasher) Maiele. Continuing his ruthless ways, in 1993, Bowman ordered the kidnapping, beating and torturing of Florida Outlaws member, Kevin (Turbo)Talley, who had signed a document with Canadian officials in Ontario admitting the Outlaws were a criminal enterprise. The betrayal led Bowman to make an example out of him for everybody in the club to learn from and Talley was ordered to report to Detroit immediately upon his release from custody in Toronto. He was picked-up at Metro Airport by two Bowman lieutenants and taken to an isolated room in the Outlaws Detroit clubhouse on Warren where he was kept detained for five days, being beaten, humiliated and sodomized. Put on a plane back out of town, Talley stripped of his colors and kicked out of the club. A decade into his reign of terror, Taco Bowman was as secure as ever in his post. He inspired a devout loyalty with his overly-aggressive antics and an intense charm and genuine affection for his troops. As a result, law enforcement had an incredibly difficult time finding a way to crack the shell of his operations and develop informants from anywhere in the proximity of his inner-circle. Being at the peak of his power after a decade in the post, Bowman had the ability to take the club in any direction he desired. Perfectly in sync with his brash persona, he chose to raise the stakes. On New Years’ Eve 1993, Bowman held a meeting of top Outlaws administrators in a Florida hotel suite and declared his intent to escalate the club’s war against the ever-hated Hells Angels. The decision was overwhelmingly well received and becomes an immediate priority. On a visit to Chicago in early 1994, Bowman ordered Chicago Outlaws president, Peter (Greased Lighting Pete”) Rogers, to begin plotting an attack on the Hell’s Henchmen, a Hell’s Angels backed biker gang based in Illinois. Upset with the untimely nature of his request, in September of that year, Bowman met with Indiana Outlaws member, Randall (Mad Dog Randy) Yager and Chicago Outlaw member, Carl (Jamming Jay) Warneke at his suburban Detroit residence and instructed them to bomb the Hell’s Henchmen’s clubhouse as soon as possible. Following two attacks on the clubhouse in the same week, the property was burned to the ground and condemned by the city. Before the year was out, Bowman had ordered more fire bombing attacks, two more targeting Midwest Hells Angels clubhouses and two clubhouses belonging to the Warlocks in the state of Florida. Not a man of an even temper, the smallest slight or sign of disrespect would send Bowman into hysterics. During the fall of 1994, he became enraged we he sees a newspaper photograph taken at the funeral of Hells Angel member, Michael (Mad Mike) Quale, killed in a gun battle with Outlaw member Walter (Buffalo Wally) Posnjak, who was also slain in the altercation. In the photo, Bowman saw a member of the Fifth Chapter motorcycle gang, an affiliate club of the Outlaws, hugging a mourning Hells Angel member. Since he was especially close friends with Posnjak, Bowman was incensed with the act of compassion that he interpreted as outright treason. In the days following the funeral, Bowman ordered the entire Fifth Chapter club, a small group of bikers based in the Southeast, to the Outlaws clubhouse in Tampa and led a mass beating of the gang’s members with chains and bats. When he was done, Bowman informed them that he was disbanding their club and they could never associate with any Outlaws ever again. Bowman ordered the murder of a Chicago-based Outlaws enforcer named Donald (Big Don) Fogg in late 1994. Fogg was a suspected informant who Wayne Hicks wound up killing on behalf of his boss. To celebrate Fogg’s execution, Bowman held another New Year’s Eve meeting, this one in Detroit, where he declared his intention to “take the war to them out west” and start attacking the Hells Angels on their own turf in California. In early 1995, he sent a group of lieutenants, headed by Hicks, out to Los Angeles to begin making arrangements for the assassination of Hells Angels Godfather Sonny Barger. While in the midst of scheming to kill Barger, Bowmen’s men blew up a number of Hells Angels-backed businesses in Southern California and began planning more attacks to take place in the coming year, including the murder of George Christy, one of Barger’s closest underlings. However, before the attempt on Barger’s or Christy’s life could be carried out, Bowman’s empire began to crack at its very foundation – Wayne Hicks aka Joe Black joined Team USA and would be the star witness against Bowman in court. Time finally ran out for Bowman in the months before the New Millennium. After almost two years as a fugitive, the FBI converged on a house in Sterling Heights, Michigan and arrested him on the afternoon of June 7, 1999 while he was socializing with Outlaws brass in the backyard. Bowman was convicted at trial in 2001.