On November 1, 1999, the penalty phase began.  The jury spent part of the first morning examining photographs of Conahan's handiwork.  Jurors looked at pictures of Richard Montgomery's corpse as it appeared at the crime scene and during the autopsy.  Wearing stern faces, the panel members examined the rope grooves on Montgomery's wrists and neck.  They were also shown photographs of Montgomery's back, which was scraped in a criss-cross pattern presumably caused from shifting back and forth against the tree while attempting escape.  One juror stared long and hard at the picture of Montgomery's groin, which was missing its genitals.

That afternoon jurors listened to Conahan’s 80-year-old aunt, Betty Wilson of Fort Lauderdale, describe him as "friendly, jovial and honest."  She testified that Conahan was dedicated to his parents, moving from Chicago to Punta Gorda to care for them.

"He helped his mother ... I saw him help her into bed," she said. "I think him being in jail hastened his mother's death."  She said his father died a few months later.

Prosecutors rested their case after Lee County medical examiner, Dr. Carol Huser, testified that Montgomery was likely conscious long enough to realize what was happening as Conahan strangled him.

Deputy State Attorney Marshall King Hall asked, "Dr. Huser, would that be a terrifying death?"

"It sure would terrify me," she responded.

During cross-examination of Huser, defense attorney Paul Sullivan asked questions about erotic asphyxiation -- cutting off breathing to heighten sexual arousal.  However, the implication that Montgomery died this way, begs the question of why Montgomery's genitals were missing, Hall was quick to point out.

"For his own twisted gratification, he strangled the victim to death," prosecutor Bob Lee told jurors in his closing statement.

At the end of Sullivan's arguments, Conahan stood and shouted to the jury, "I do not know Mr. Montgomery, nor did I ever!"

Blackwell had bailiffs rush the jury out of the courtroom and told Conahan that if he made one more outburst he would be gagged or removed from the courtroom.  He then gave Conahan a choice, he could behave himself, be bound and gagged or leave.  Conahan said he wanted to leave.  Defense attorney Mark Ahlbrand advised Conahan to reconsider his decision.

"This is going to look bad," Ahlbrand said.

"I'm not going to sit here while he tells them I'm a murderer," Conahan responded, "I did not kill this man."

"If you sit there, you have a fighting chance," Ahlbrand said. "If you leave the courtroom, they'll think you're arrogant and don't care."

 Conahan decided to stay, and kept quiet for the remainder of the proceedings.

On November 3, the jury began deliberations on whether Conahan should be executed or spend the rest of his life in prison.  After deliberating for just 22 minutes, the jury recommended that Judge Blackwell execute Daniel Conahan for the murder of Richard Montgomery.

It would now be up to Judge Blackwell to decide whether to follow the jury's recommendation to execute Conahan in Florida's electric chair or sentence him to life in prison.  Judges rarely deviate from a jury's advice when it comes to sentencing.

On December 10, 1999, Judge William Blackwell made his decision.

"It is obvious that during this ordeal, Montgomery was confined or imprisoned against his will," Blackwell read from a document. "Such confinement against his will was for the obvious purpose of inflicting bodily harm upon the victim or terrorizing him."

“The crime was especially heinous, atrocious and cruel”, Blackwell said. ‘Two medical examiners testified that many of Montgomery's wounds were inflicted before he died.”

"May God have mercy on his soul," said Judge Blackwell as he sentenced Daniel Owen Conahan Jr. to death.

Conahan gave little reaction as Judge Blackwell read the order that he be put to death in Florida's electric chair.

"We felt all along that the evidence clearly showed the defendant was guilty and that the death penalty was warranted," Assistant State Attorney Marshall Hall said.