"In 24 years, that was my worst day," said Monroe Sheriff's Captain, John Kennedy.
March 31, 2011 will go down in Monroe County Jail history.
"You live through something like that, you want to make sure that it never happens again. "
When Captain Kennedy arrived for his overnight shift that night, inmates Eddy Palmer and Joseph Mitchell had already escaped from cell 207.
"You believe that you're ready for anything and than something like this happens and it's a shock to your system."
According to a state investigation, the men carefully crafted their escape for weeks.
"It was a frustrating day, obviously," explained Sheriff Patrick O'Flynn.
The men were able to saw at the base of a steel window bar to escape using blades smuggled in by attorney, Rudy LePore. It's something that Kennedy is still haunted by.
"If I could change one moment, it would have been stopping Rudy LePore from coming in with those blades."
Ali: "Sheriff, who's to blame for the break?"
Sheriff: "I don't think there's anybody directly to blame. Obviously, we've disciplined people and we've let people go."
Since then, they've made more than a dozen changes to jail operations. But, they started with replacing the windows. Each are now a five inch pane of glass surrounded by solid steel.
"We've got a state of the art camera system, we've got good lighting, we've got barrier fencing out around the perimeter where we always felt was a vulnerability," explained the sheriff.
"From the sheriff on down, we were notified to look at everything, look at it critically, and make changes where changes need to be made," added Kennedy.
After all, the blades weren't the only reason the men were able to break free.
A state report sited jail personnel for incomplete cell tours.
The report also says blind spots from the supervisor's post may have contributed to the incident.
The sheriff doesn't entirely agree with the report. Regardless, he says they've complied with all 19 state corrections recommendations.
"It's still in the forefront of most of our minds, if not everybody's mind. A lot of decisions are based on that and never wanting that to happen again," said Kennedy.
"We're really proud of where we are when it comes to some of the changes," O'Flynn explained. "No one is going to be getting out of here in any way like they got out of here."
Mitchell was supposed to be sentenced last month. But, the court hearing was postponed.
He faces up to seven years in prison for the escape.
Palmer is currently serving 3 1/2 to 7 years for the break.
Rudy Lepore pleaded guilty to his charges and was sentenced to five years probation and 200 hours community service.