The Outlaws Motorcycle Club down in Florida lost a brother this week with the fatal stabbing of seasoned Jacksonville chapter lieutenant Christopher (Louie the Lip) Keating in a Daytona Beach bar fight, but recently gained two club elder statesmen with the release from prison of legendary South Florida biker lords, James (Big Jim) Nolan and Fred (Yankee) Hegney. Big Jim Nolan is the Outlaws overall patriarch in the Sunshine State and the South Florida chapter’s revered Godfather and has been behind bars for the majority of the last 40 years. Yankee Hegney was the South Florida chapter’s vice president when he got sent away in the late 1980s.

The 74-year old Nolan, who officially planted the Outlaws flag in Florida in 1960s and served as regional president for more than a decade, got out of the can back in the fall – he walked free in October 2016. Hegney, 76, was sent to a Miami halfway house last month and got his final walking papers Friday morning. They were convicted together of federal racketeering charges in 1989. At the time of their trial, Nolan had been locked up since 1981 on an unrelated gun case.

Nolan originally founded the Iron Cross Motorcycle Club in the early 1960s, eventually “patching over” the club under the Outlaws banner later in the decade. The Outlaws South Florida chapter, the first in the state, traces its roots to the summer of 1967 and Nolan getting the blessing from the club’s administrators in Chicago to open shop in the area (the patch over ceremony took place in Kitty’s Saloon in Juno Beach). American biker historians credit Big Jim Nolan with being the man who convinced the Midwest-based Outlaws leadership of the importance of the country’s southern region and the state of Florida specifically, which proved quite prophetic.

Yankee Hegney was born in Queens, New York and got to South Florida in 1973. He didn’t “patch-in” with the Outlaws until 1980, but was integral to the club’s drug-trafficking affairs during the 1970s. Under Nolan’s stewardship, the Outlaws in Florida shifted their main focus from prostitution and gambling to narcotics just as the nation’s disco era hit and demand for party drugs were on the way to reaching a fevered pitch.

Big Jim was first locked up in 1978 on state drug charges and for threatening to sick his dog (a 150-pound Great Dane) on a Hollywood, Florida police officer. He was released in September 1980 and began splitting his time between Ft. Lauderdale and Tucson, Arizona, where he was hoping to expand Outlaws operations to.

In August 1981, Nolan was arrested for illegal firearm possession connected to the July 11, 1981 shooting death of John McQuillen at a Tucson biker bar called the Bashful Bandit. He wouldn’t breathe the air of a free man again until just a few months ago (Big Jim was acquitted of the murder under a successful self-defense plea, but convicted of the weapons charge and slapped with a 10-year prison sentence).

Big Jim Nolan

On June 3, 1986, most of the South Florida Outlaws chapter was indicted in a giant federal racketeering case. Big Jim Nolan and Yankee Hegney were the two headlining defendants. The case covered chapter activity from 1970 through 1985, a spree of massive violence and thuggery rampaging through Broward County for the better part of two decades, and named a number of gangland murders as predicate acts of the indictment.

The trial of six South Florida Outlaws leaders was a marathon affair. It began in early December 1987 and lasted until 1989, becoming the longest trial in the history of the federal district court in Ft. Lauderdale. Both Nolan and Hegney were found guilty of racketeering and Hegney was nailed on drug charges. They received twin 25-year prison sentences.

During the landmark trial, Nolan was linked to the ordering of multiple slayings, the extortion of one girlfriend and her lover for $40,000 and the brutal beating of another girlfriend of his that he used as a deterrent to others that may decide to cross him. Hegney was tied to the massacre of four rivals at a Ft. Lauderdale residence.

Nolan allegedly ordered the triple murder of three rival Hells Angels biker gang members from Massachusetts in the spring of 1974 after the trio of Hells Angels attacked a South Florida Outlaw at a Manhattan New Year’s Eve party the year before. The three bikers were reportedly lured by Big Jim from a Ft. Lauderdale bar to their slaughter at a nearby gravel pit under the pretense of a peace conference. Instead, they were killed execution style. The following year, Nolan would be acquitted at trial of state murder charges.

According to trial testimony, two months after the hit on the east coast Hells Angels, Nolan instructed fellow South Florida Outlaw Don (Gangrene) Sears to murder his girlfriend Naomi Sinoqub for the belief that she intended on going to police to give them information on the chapter’s prostitution ring. Sears, a co-defendant of Nolan’s in the case, kidnapped Sinoqub with another lieutenant in the Outlaws, Richard (Dirty Dick) Brainard and the pair took her out on Brainard’s boat, shot her in the head, slit her throat and dumped her body in the Atlantic Ocean.

Nolan’s affairs of the heart also made it into testimony. When in July 1977, his girlfriend Tina Wittenstein left him for a customer of hers at the topless bar she worked at, Big Jim had them kidnapped, viciously beaten and held until her new boyfriend gave the Outlaws $40,000 of a demanded $100,000 ransom.

Big Jim beat another girlfriend of his so bad in 1981 that he put her in the hospital with broken ribs and a broken jaw from crushing her face with his bare hands as she screamed for help. Per witness accounts, Nolan paraded other woman in front of his hospitalized girlfriend as an example to them as to what happens if they get him angry.

One witness remembered being told: “You see what I did to her? And I’m in love with this bitch. I don’t even like you’re motherfucking ass. So go ahead and try to piss me off and see what happens.”

Nearly two years after Nolan got locked up on his weapons case, Yankee Heglen and Outlaws lieutenant and explosives expert Clarence (Big Smitty) Smith supposedly participated in a heinous mass murder. In February 1983, Smith was in a beef with Fernando Stefano, a non-Outlaws affiliated drug dealer, who had kidnapped and sexually assaulted Smith’s girlfriend in retaliation for a perceived previous slight, and recruited Hegney to help him get revenge.

Per police records, Smith and Hegney broke into Stefano’s home in the middle of the night, shot him at point-blank range in his bed and then did the same with three of his houseguests, Tommy Young, David Bostic and Wendy James. Stefano’s fiancé Penny Reid survived being shot in the face and identified Smith as one of the assailants. Bostic fingered Yankee Hegney to responding emergency medical technicians as the man who shot him just before he died. State charges were filed and dismissed prior to trial.

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