How Dalia Dippolito is managing prison life and her legal team's hope for a new trial

Dalia Dippolito has been called many things over the course of her rollercoaster legal saga: a “monster,” an “evil” woman who wanted her husband dead, a “black widow.” But her longtime defense attorney argues she is something else entirely.

“Dalia is the most misunderstood woman in the United States,” Brian Claypool, her attorney, told “20/20” in a recent interview. “The perception that people have in the world about Dalia does not equate with the Dalia that I know.”

“20/20” has been following the wild twists and turns of Dippolito’s case for over a decade. She became one of Florida’s most notorious courthouse celebrities after she was accused of a murder-for-hire plot against her now ex-husband and later used a quest for reality TV fame as part of her defense.

After three trials and two convictions, the 37-year-old is currently being held at the Lowell Correctional Facility in Marion County, Florida. Claypool began representing Dippolito after her first trial, and her defense team said it hopes to succeed at one last shot at getting her a new trial.

“She was never a career criminal. In fact, Dalia Dippolito didn't even have a criminal record when this all went down,” Claypool said. “Dalia is resilient. She has not given up hope for getting a new trial.”

Dippolito was recorded on camera by Boynton Beach police in 2009 discussing plans to hire a hit man with a friend, and then meeting with an undercover police officer posing as a hit man to discuss killing her then-husband, Michael Dippolito.

The friend had reached out to police after Dalia Dippolito initially sought his help with her plan, and he then worked with Boynton Beach police in their sting operation against Dippolito.

Police cameras were again rolling on August 5, 2009, when Dalia Dippolito arrived home to find what she thought was a real crime scene of her then-husband’s murder. In fact, it was an elaborate fake crime scene, created by Boynton Beach police. It was there that they recorded her emotional reaction as officers told her he was dead. By then, officers had already removed Mike Dippolito, very much alive, from the home. They took Dalia Dippolito to the police station under the guise that they needed her to tell them whom she thought might be behind the killing.

Once she was in an interrogation room, police recorded her reaction as they revealed to her that not only was her husband still alive, but that they had taped her conversations with the friend and the supposed hit man, who was really an undercover Boynton Beach police officer.

She was immediately arrested for solicitation to commit first-degree murder.

Meanwhile, the reality TV show “COPS” had been filming alongside the Boynton Beach Police Department on the day officers set up the fake crime scene and arrested Dippolito.

At the time, the Dippolitos had been married for just six months. Prosecutors argued Dalia Dippolito wanted control of the couple’s Palm Beach County townhouse and her husband’s bank account. They also argued that she wanted him out of the way so that she could rekindle a relationship with an old boyfriend.

Dalia Dippolito has always denied that she wanted her then-husband dead. At her first trial, her attorney claimed that she knew she was being recorded by police and that her husband came up with the idea of creating a murder-for-hire video in hopes of posting it online and gaining reality TV fame. Her attorneys argued their hit man scenario was fake and that she and the friend were acting.

Both Michael Dippolito and the friend denied these claims.

In 2011, Dalia Dippolito went to trial for the first time and was found guilty of solicitation to commit first-degree murder. The judge, who called the murder-for-hire plot "pure evil," sentenced her to 20 years in prison.

"It makes you realize how serious what was really going on was," Michael Dippolito told “20/20” in a 2011 interview after the verdict. "It's just something you can't imagine anybody could really, really do. It was so senseless for a girl, my wife … to take those steps to do that. It was so unnecessary."

But an appeals court judge ruled in 2014 that the jury for her first trial was improperly selected and tossed out the conviction.

She faced a second trial in 2016, again charged with solicitation to commit first-degree murder.

At her second trial, Claypool abandoned the reality TV defense that had been argued at the first trial and instead took aim at the Boynton Beach Police Department, accusing it of misconduct by staging the fake crime scene for the TV show “COPS.” He alleged that the department made the fake scene “way more than it ever was” for the purposes of television.

“The presence of the 'COPS' TV show created a frenzy within the Boynton Beach Police Department to manufacture good television,” Claypool told “20/20” in a 2015 interview.

The Boynton Beach Police Department denied any wrongdoing and said they were gathering evidence against Dalia Dippolito.

“'COPS' filming with the Boynton Beach Police Department had nothing to do with this investigation," Boynton Beach Police Public Information Officer Stephanie Slater told "20/20" earlier this month. "It was just a coincidence as far as timing was concerned. The men and women of the Boynton Beach Police Department did an incredible job on this case, and Mike Dippolito is alive and well today because of it."

Dippolito's 2016 retrial ended with a hung jury, and a third trial date was set.

While awaiting her second trial after her conviction was overturned, Dippolito was under house arrest at her mother’s home. She became pregnant during that time and gave birth to a son.

At her third trial in 2017, a jury returned a verdict in just 90 minutes. Dippolito was again convicted of solicitation to commit first-degree murder. She was sentenced to 16 years in prison.

In September 2019, the Florida Supreme Court rejected without comment a request from Dippolito for the court to review her 2017 conviction. Her defense team had tried to put the case before the U.S. Supreme Court, but in February the court declined to hear it.

“We’re still fighting,” Claypool said. “We plan on filing a motion with a federal judge asking that judge to review the third trial for constitutional violations against Dalia Dippolito. So we have one last chance to get Dalia a new trial... we haven't given up hope.”

While serving out her prison sentence, Dippolito has been leading a bible study group behind bars, Claypool said.

“She's very well respected in jail for her faith,” he said.

He added that she still gets to see her young son, who is 4 years old, and that his grandmother is caring for him in the meantime.

“It's very painful for Dalia to be in jail and to not be around her son. It's breaking her heart," Claypool said. "Dalia truly misses the fact that she cannot be around her son more.”