“Sweat seemed to be the mastermind, not only of the escape, but the leader, if you will, when he got out,” New York State Police Maj. Charles Guess told ABC News’ “20/20.”
Their bond formed inside the maximum security prison in Dannemora, New York, where Sweat, 34, and Matt, 48, were close buddies.
Sweat ended up at the prison in 2003 after pleading guilty to killing Broome County Sheriff’s Deputy Kevin Tarsia to avoid the death penalty, which was still in effect in New York at the time. A few years later, Matt, who had finally been brought to justice for killing 76-year-old William Rickerson, joined him.
The two murderers became friends and eventually had their request to become neighbors in Clinton Correctional Facility’s “honor block” approved.
“The inmate that was next to Matt at the time agreed to swap. And so the swap took place,” Clinton County District Attorney Andrew Wylie told “20/20.” “Who would have known that that may have been the start of this plan?”
Inmates on the honor block were allowed out of their cells for “the majority of the day,” Erik Jensen, a former inmate at Clinton Correctional Facility who served time with Matt and Sweat, told “20/20.”
“They have what you call rec time on the flats, which is on the lower level, where they can get out, watch TV ... they have cooking privileges,” former Clinton Correctional Facility guard Mark Drone told “20/20.”
As they walked the prison yard, Matt and Sweat passed over a sort of speed bump that authorities said they later realized was the very pipe they needed to crawl through to get underneath the prison’s massive walls.
“So every day, they had this, you know, layout of their, you know, potential escape route that they were looking at,” said Wylie.
Plotting an escape plan would not have been unusual for Matt, who broke out of Erie County Correctional Facility in June 1986 by reportedly scaling the jail’s barbed wire fence. And Sweat, who meticulously planned his past crimes by making lists and maps, may have contributed these very skills to their escape plot, authorities said.
Matt also had the art of persuasion, which authorities said he used to talk their supervisor at the prison tailor shop, Joyce Mitchell, into helping them.
After months of planning and sawing their way to freedom, authorities said, Matt told Mitchell on June 5 they were finally going to make their escape that night and to meet him and Sweat at the power plant at midnight.
But after making their way through the holes they had carved into the pipes and emerging at the manhole by the power plant, Mitchell didn’t meet them with the getaway car.
“They had total faith that she was going to pick them up at the manhole at midnight, and when she got cold feet and didn’t show up, they had to regroup, they had no plan,” New York State Police Superintendent Joseph A. D'Amico told “20/20.”
Mitchell, 51, has pleaded not guilty to promoting prison contraband and criminal facilitation. Prison officials had earlier investigated Mitchell for a suspected relationship with Sweat during the past year, but no action was taken against her at the time.
Mitchell’s lawyer said she consistently denied the allegations. She is expected to appear in front of a grand jury at the end of July.
Soon after Matt and Sweat escaped, people pulled up to a house on the block near the prison and asked them what they were doing on their yard. Matt started to freak out, but authorities said Sweat told them he stayed level-headed and convinced Matt to follow him into the woods.
Weeks after their escape, authorities found more evidence that Sweat was the more careful criminal while Matt was a dangerous and erratic one.
On June 20, just 20 miles outside of Dannemora near Owls Head, New York, cabin owner John Stockwell and his dog stopped by his unlocked hunting cabin and immediately saw signs of activity inside.
“He saw essentially a flash of what he presumed to be a human kind of step back out of view from this window pane,” Maj. Guess said. “Whoever was on the back deck fled down the back, and he could tell that because he could hear the crashing through the brush.”
Inside, Stockwell said he found more signs of activity, including a misplaced coffeepot, a missing shotgun and a map ripped off the wall, and alerted authorities.
Guess said Sweat later told them that Matt was prepared to take Stockwell hostage with the shotgun in the cabin, but Sweat was able to convince him to leave. However, in their rush to flee the scene, Matt left vital clues behind.
“Items of interest that we recovered fall out of Matt’s pack: toothpaste, toothbrush, razor, these kind of personal grooming items, which immediately were a hit on DNA within the next 24 hours,” said Guess. “It helped us sharpen our focus. And certainly boosted the morale of everyone involved.”
And authorities later learned that Sweat was getting fed up with the increasingly unstable Matt and decided to ditch him.
“Sweat knew that Matt was out of shape. Any of these cabins where he could find alcohol, he would drink and try to-- and get drunk,” Guess said. “As his frustration level grew, he talked increasingly about harming members of the public or law enforcement, and Sweat really apparently wanted no part of that. He wanted to continue his odyssey and escape.”
After Sweat abandoned him, Matt moved on, but on June 26 he found himself surrounded by police in Owls Head. Hunkered down, he lay down in the woods and took aim at agents on patrol from the woods with a 20-gauge shotgun. But as he prepared to shoot, he coughed and betrayed his position to the border patrol national tactical team. When he refused to comply with border patrol agents, authorities said, Matt was shot three times and killed.
Sweat, despite appearing to be the mastermind of the escape plot, also made a mistake that led to his capture. After ditching Matt, Sweat later told authorities that he traveled at night, avoided locals and even shaved his face. It was when the crafty con became anxious and decided to move in the daylight that he was spotted by Sgt. Jay Cook, a local trooper who was supervising a team in the Constable, New York, area for Guess’ team.
After chasing Sweat through an alfalfa field, Cook shot at Sweat twice, hitting him in the back and upper torso. Sweat kept running after being hit by the first bullet, but after the second bullet, he dropped on the ground and was quickly taken into police custody.
Sweat was brought to Albany for treatment for a collapsed lung. On his way back to prison, authorities said Sweat continued to brag about the escape.
“I think he boasted a bit, no doubt about it,” D’Amico said.