In 1989, Nolan was convicted for numerous violations of the Racketeer Influenced and Corrupt Organizations Act, including ordering several murders, extortion, and narcotics and prostituting offenses, and sentenced to fifty years in federal prison.
[1][4] Nolan was described by the Sun Sentinel as "an intelligent and charismatic leader" who sported "long, wavy brown hair well below his shoulders and a full beard".
[1] The Outlaws were quickly implicated in prostitution, narcotics, car theft, stolen credit cards, grand larceny, assaults and other crimes, but it was an incident on November 14, 1967, in which five Outlaws members crucified an 18-year-old woman, Christine Deese, by nailing her to a tree in Jupiter after she failed to turn over $10 demanded by the bikers, that gained the chapter most of its notoriety and resulted in Florida Governor Claude R. Kirk Jr. vowing to drive the club out of the state.
The crime reporter Scott Burnstein described him as "the Outlaws overall patriarch in the Sunshine State and the South Florida chapter's revered Godfather".
[3] Nolan was instrumental in the Outlaws' rapid expansion throughout the state during the 1970s, as the club amalgamated various smaller motorcycle gangs, such as the Regents in Jacksonville and the Iron Cross in Orlando.
[9] The bikers maintained control over these women using various methods, including gathering information on and threatening the lives of their families, and would occasionally buy and sell their old ladies amongst themselves.
[7] Under Nolan's leadership, the Outlaws shifted their focus in the mid-1970s from sex rackets, due to a decline in prostitution income, to illegal gambling and narcotics trafficking at a time when the demand for party drugs was at an all-time high at the peak of the disco era.
[10] The Florida faction of the Outlaws gained power and influence within the club by forging links with Colombian and Cuban drug suppliers, sourcing cocaine being imported into the state from Colombia, which they then distributed to chapters in the Midwest and on the East Coast.
When Rogers returned to New York to attend a New Year's Eve party in Manhattan in 1973, he was severely beaten by Alexander after allegedly raping the Hells Angel's wife.
[7] Two of the bikers — "Whiskey" George Hartman and Edwin "Riverboat" Riley — were visiting the state to supervise the covering up of gang tattoos belonging to Albert "Oskie" Simmons, who had relocated to Orlando to operate a motorcycle shop after leaving the Lowell Hells Angels a year or two earlier.
[19] Nolan called a club meeting to discuss what course of action the Outlaws should take regarding the presence in their territory of the "maggots" who had beaten their "brother" Peter Rogers.
[20] When the Hells Angels arrived at the Outlaws' clubhouse, however, Nolan ordered several fellow club members to take the rival bikers to a deserted area and "make sure they don't come back"․ Four Outlaws — Henry "Funky Tim" Amis, William "Gatemouth Willie" Edson, Norman "Spider" Risinger, and Ralph "Lucifer" Yannotta — then forced the Hells Angels into the back of a van at gunpoint, bound them with pink clothesline and drove them to a quarry in the Everglades of southwest Broward County near Andytown, where Risinger killed each of them execution-style with a 12-gauge shotgun.
[20][25] In 1977, the Hells Angels attempted to resolve the feud between the clubs by sending Sandy Alexander, along with Oakland, California chapter members Sergey Walton and Gary Popkin, to meet with Nolan and other Outlaws leaders in Durham, North Carolina.
[26] Along with Amis, Edson, Risinger and Yannotta, Nolan was indicted by a grand jury in connection with the killings in April 1978, charged with three counts of first-degree murder.
[3][14] State prosecutor Thomas Kern characterized Nolan as "the undisputed leader of the Outlaws in South Florida" and asserted that he was responsible for ordering the three murders.
[6][7][20] In August 1974, a woman named Joyce Karleen was invited, on the offer of finding a job, from Daytona Beach to stay at a trailer home in Hollywood, Florida, which she later discovered was the Outlaws clubhouse.
[7][29] The Outlaws tied Karleen to a chair at the clubhouse and stripped her of her blouse before each took turns punching and kicking her and then using a hot spoon to sear her repeatedly on her arms and breasts.
After they had finished torturing Karleen, the bikers escorted other Outlaws old ladies into the room while she remained tied to a chair, and warned the other women that they would receive the same treatment if they misbehaved.
[7] Shortly after the incident, Naomi Sinoqub, the old lady of Outlaws member Donald "Gangrene" Sears and one of the women who was with Karleen the night she was beaten and tortured, ran away from the club.
[2] After he was paroled in September 1980, Nolan began dividing his time between Fort Lauderdale and Tucson, Arizona, a city he planned to bring under the Outlaws' sphere of influence.
[3] Nolan convinced the parole board that he was working for country musician and Outlaws member David Allan Coe, although he was actually making a living in Arizona from the prostitution of his old ladies and drug dealing.
[7] In March 1981, Nolan hit Geoghagen several times and called one of his other old ladies to take her home when she stumbled into a parked motorcycle at a biker bar after a night of partying.
[7] After Geoghagen returned to Florida in April 1981, Nolan arranged to purchase another woman from his long-time Outlaw friend, "Sad" Sam Nail, to make up for the lost prostitution income.
[34] The court took several steps to control prejudice at trial, including moving proceedings from Tucson to Phoenix, and excluding any references to Nolan's motorcycle gang connections as well as evidence derived from wiretaps of his telephone.
[2][6] On June 3, 1986, the majority of the Outlaws' South Florida chapter — including the already-imprisoned Nolan and his vice president, Fred "Yankee" Hegney — were indicted in a federal racketeering case, which covered a series of crimes in Broward County between 1970 and 1985.
[35] Federal prosecutors portrayed the Outlaws on trial as members of a criminal enterprise bound by a "code of silence" who profited from drug dealing and prostitution and who evaded arrest for fifteen years by intimidating and killing witnesses to their crimes.
"[10] Defense attorneys maintained that even if the defendants had committed each crime listed in the indictment, the acts were not carried out for the benefit of the Outlaws organization, and contended that some prosecution witnesses had been paid as much as $70,000 by the government and had charges against them dismissed in exchange for their testimony.
These acts included ordering the murders of George Hartman, Edwin Riley, Albert Simmons, and Naomi Sinoqub; the extortion of Joyce Karleen, Tina Wittenstein, Vaughn Foreman, and Iris Geoghagen; and narcotics and prostitution offenses.
The Reverend Daniel Burgoyne, who had a jailhouse ministry in Tucson, testified that he was convinced of Nolan's sincerity after observing the biker "sobbing and crying before God", and said: "He never missed a Bible study.
Sergeant Bob Faulkner of the Broward County Sheriff's Office concurred, saying: "I don’t think they’ll ever have a leader again with the charisma of Jim Nolan.