The Case's Early Days
Timothy Dumas, a former Greenwich resident and the author of Greentown: Murder and Mystery in Greenwich, America's Wealthiest Community, tells A&E Crime + Investigation, “Steve Carroll, one of the original detectives on the case, suggested [the police] were ‘too nonchalant,’ perhaps because the Skakels appeared to be open and cooperative, and not as though they might be hiding something."
“I think it goes deeper. There seems to have been an upstairs-downstairs thing at work,” Dumas continues. “Several police had driven for the Skakels or done other work for them. The police were well aware of the Skakels’ money, power and influence, and surely dreaded going up against them.”
However, Connecticut's former chief state's attorney Richard J. Colangelo Jr. , who oversaw a review of the Moxley case from 2019 to 2020, disagrees. “I don't believe that the police acted in any way differently with this case than any other one during that time period," Colangelo, now a professor at the University of New Haven, tells A&E Crime + Investigation.
Investigation Reopened
In 1991, another Kennedy cousin, William Kennedy Smith, was accused of raping a woman in Palm Beach, Fla. (He was eventually acquitted at trial.) Amid coverage of this case, rumors spread that he’d been in Greenwich when Martha was murdered. The rumors weren’t true, but the interest they sparked led to an in-depth article by Leonard “Len” Levitt, which had been denied publication for years, finally appearing in Greenwich Time and The Stamford Advocate in June 1991. The story revealed the deference police had exhibited while investigating the Skakels.
Two months later, police reopened the investigation into Martha’s murder. This provided an opportunity for Dorthy Moxley, Martha’s mother. (Her father had died in 1988.)
“Dorthy began taking a public role in Martha’s case around 1991, when the case got an unlikely second wind,” Dumas says. “She told me that the last thing she could do for Martha was to seek justice.”
Dorthy’s advocacy, books like Greentown and Murder in Greenwich: Who Killed Martha Moxley? by former LAPD detective Mark Fuhrman and ongoing news coverage helped keep the case alive. In 1995, a story broke about a private investigation the Skakels participated in. Tommy had admitted to being with Martha until almost 10 p.m., later than he’d originally said. In addition, Michael had told investigators he’d masturbated in a tree on the Moxley property that night, though he’d previously told police he’d gone to bed after returning from a cousin’s house. Michael described the same behavior on tapes made for an autobiography that never got written.
A Conviction, Finally
A one-judge grand jury was convened in June 1998 and investigated for a year and a half. 
In January 2000, Michael was arrested and charged with Martha’s murder. His trial began in April 2002. The prosecution argued Michael had been in a jealous rage after Martha flirted with his brother, Tommy.
Several former classmates from Michael’s time at a residential school for troubled youth took the stand. One said Michael told him of Martha’s death, “I must have done it. I did it.” Two others said Michael admitted he’d been drunk that night and couldn’t remember his actions, with one also mentioning that Michael had expressed jealousy over Tommy “stealing” Martha from him.
In June 2002, a jury found Michael guilty. Dorthy and Martha’s brother, John, were present for the verdict. Michael received a sentence of 20 years to life that August.
Conviction Vacated
From behind bars, Michael spent years pursuing different appeals. In October 2013, a judge agreed that his lawyer had provided inadequate representation and ruled that he should receive a new trial. Michael was granted bail the next month.
It fell to Colangelo, then a state’s attorney, to determine if Michael could be prosecuted again. Along with Steve Jacobs, a police inspector at the state’s attorney’s office, he reexamined the case.
“It was so many years after the fact that there were witnesses that were no longer with us,” Colangelo says. “There were witnesses that, even though we had prior testimony from them, didn't remember anything that they had said or what had happened.”
Colangelo and his team tried to find new evidence. “We sent Martha's clothing and other pieces of evidence up to the lab to see if there's any touch DNA,” he says. “We were not able to recover any additional forensic evidence that would have helped with the prosecution.”
They also searched for new witnesses. “We looked to see if there was any information that came out in any of the civil proceedings that potentially could have been an additional witness, or anybody that wasn't involved in the initial trial,” Colangelo says. In the end, Colangelo says, “We were looking at the same case, the same evidence, through, realistically, the same lens, to see if we could replicate the conviction. And we just didn't believe that we could.” 
In October 2020, Colangelo announced the state would not retry the case.
Aftermath
“When [the case] first came back to me, I had a conversation with Mrs. Moxley,” Colangelo says. “I promised I would make sure that we didn't leave any stone unturned.”
Colangelo says Dorthy accepted the conclusion he came to: “She understood what it would take to prove the case, and understood that I didn’t believe that we could prove it beyond a reasonable doubt.”
“Yes, she was incredibly dismayed when the conviction was vacated,” Dumas says of Dorthy. “But she believed the truth had outed, and she was at peace.”