MIAMI (CBSMiami) – A chapter in South Florida’s cocaine-dominated history that came to defined the 80’s as the “Cocaine Cowboy” days played out in court Thursday.

The attorney for reputed Cocaine Cowboys hit man Jorge Ayala said in court Thursday that this was his client’s “last chance and otherwise he will die in prison.”

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Ayala who was convicted in three murders and suspected in 35 drug-related slayings has spent the past 26 years mostly in a prison in Northern Florida.

But now, the 48-year-old wants out. On Thursday, he sat wearing a red inmate jumpsuit before Miami-Dade Circuit Judge Migna Sanchez-Llorens saying nothing and allowing his attorney Jim Lewis to speak for him.

Lewis asked a judge for a chance to present evidence that he says would prove the State Attorney’s Office made a deal with the reputed killer 25 years ago in exchange for his cooperation.

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Circuit Judge Sanchez-Llorens shot down his request saying the motion that could have reduced his jail time was filed 20 years too late. She added that “it was not in her jurisdiction.”

Ayala agreed to cooperate against the head of Miami’s drug cartel back in the 80’s Griselda Blanco who served two decades in prison and later was deported back to Colombia where she was gunned down last year. In exchange for his cooperation, Ayala’s attorney said verbal agreements were made with prosecutors that would have allowed him to have his sentence reduced.

But Ayala’s ability to engage the secretaries in a phone sex scandal embarrassed the Miami-Dade State Attorney’s Office at the time and dealt a blow to Blanco’s prosecution.

Lewis said that incident continues to haunt his client’s ability to receive fair treatment.

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“Because supposedly he made some phone calls or had some phone sex conversations with some State Attorney’s secretaries now all of a sudden they can say, ‘ Well, you messed it up. You blew the agreement.’ You know everybody needs to get over that,” Lewis said after the hearing. “He put himself and his family at risk.”