​Amanda, Pete and Rob were new to the jailbreaking business. If Rob had not been wrongly convicted of assault, none of them would have ever thought of orchestrating one. College degrees and well-paying jobs did not a conspiracy to commit a felony make.

They were three months in the planning and a few hours from executing a plan to break Rob out of the Cheshire Correctional Facility, a medium-security prison in the middle of Connecticut. 

Amanda and Pete were sitting in a breakfast nook at their condo in Branford overlooking the Long Island Sound. Amanda had just poured them coffee and Pete was plucking grapes from a bowl while looking intently at a hand drawn map.

Amanda said, “Do you think we have estimated the blackout time properly? It makes me nervous that we only give Rob 15 seconds to get from the middle of the exercise yard to the fence.”

“Unfortunately,” replied Pete, “That is one of the many SWAGS we had to make. We had to guess the location of the guards on watch, etc. We are at the stage where we should focus on executing the plan, not second guessing our assumptions. There were a lot of assumptions in the ‘Brinks Job‘ too.

Amanda replied, “I know. It’s just this is finally sinking in. We’re breaking a felon from prison! It’s not a damn movie, we’re actually going to do this!”

Pete reached across the table and stroked his wife’s hand. “Thanks for the coffee,” he said, “We have to remind ourselves why this is necessary. Not the right thing to do, not a crusade, but something that must be done.”

Amanda nodded and looked at the map. Pete was pointing to the northwest corner of the prison yard. This was where they had been able to dig a two-foot tunnel under the fence a mere six hours ago. She recalled, “I remember when you first thought of this and I thought you were batshit crazy. Now, I can’t believe how easy it was to pull off. A few public records from the town hall and befriending one of the prison guards was all we needed to figure it out.”

“Don’t forget the tricky part of getting a two-way radio into Rob. The drone diversion you planned was brilliant!”

Grinning Amanda said, “Thanks, I guess being able to talk to Rob, was a critical part. I’m shocked that the inner fence is electrified but has no concrete foundation, while the outer fence has solid concrete under the perimeter but is not electrified.” 

“Yes,” said Pete, “When this is over, ‘they’ will certainly question the design. A gap cut through the outer fence and a ‘Great Escape’ tunnel dug under the inner. So simple a breach risk unnoticed for the 50-year history since the prison opened…just like ‘Escape from Alcatraz’.

“Love Steve McQueen,” crowed Amanda.

“That’s why I’m calling you ‘Bullitt’!” Pete laughed.

They went back to discussing the plan details. Pete gained confidence as they re-reviewed the plan. Amanda was slow to dispel doubts. “The assumption…”

Pete cut her off, “Assumption. That word is banned from conversation until this is over. Capiche?”

“Capiche,” she fake smiled.


Rob sat in his 10 x 10 cell and continued a running dialogue with himself. Skeptic Rob battled with Upbeat Rob:

Skeptic Rob:

God, I can’t believe I’m going through with this. So many things can go wrong with the plan.

Upbeat Rob:

Just think about all the detailed planning. Pete and Amanda are the best.


It’s not the confidence I have in my friends, it’s all the assumptions. Yes, I was able to give them paced off dimensions and yes, I gave the recreation routine and schedule, but blacking out the prison and getting under one fence and through another in 15 seconds, is a stretch and the timeframe is, well, a complete guess!


It’s a conservative estimate. If I were to call it a guess, I would use SWAG. Even without rehearsing you know it’s only 60 feet of ground to cover. Remember breaking 12 seconds in the 100-yard sprint in school? This is only 20 easy yards.

He laughed at himself as he took a pace and spun around to represent each side of the discussion. Prison may be getting to you, thought Real Rob. He realized now was the time to rehearse the plan in his mind yet again. 


Tonight, at rec break, do exactly as I have done for the last month.  I will have the contraband radio on my person, so don’t scratch my nuts. At the five-minute mark, I proceed to a spot in the northwest corner, ten paces from the fence facing inward. I hit the transmit button on the radio and hold it for five seconds. Pete and Amanda will know I’m ready. 

After the power goes out, I pivot 180 degrees and run like hell to the spot. Find the dirt covered plank of wood, slide it aside and slither under the de-electrified fence. Turn 45 degrees to the north and run to the exterior fence where Pete will be with the fence spread open; the same gap they used the previous night to access the inner fence. 


That’s enough! You can leave out the final steps of darting to the large oak tree where two Vespas are hiding under sticks and leaves. Traversing an open field to Rte 10 where you make a turn into the alley near the clock tower and ride the Vespas up the ramp to an idling moving truck with Amanda in the driver’s seat. Nothing could go wrong with this?


Dammit, I’m Andy Fucking Dufresne! I didn’t even get to the part when the lights come on.


You don’t have to. This should happen when Pete and I are almost to the Vespas. The search lights will come on automatically; protocol after an outage. The prison guards will assume the worst but will not know what, who or where. We’ll almost be to Rte 10 when they spot us. This is the part where Pete and I get shot from a sniper rifle.


It’s a medium security prison. Amanda told us they will not fire for any reason unless someone’s life is in danger. She was confident of this as her new guard friend had told her.


A lot of things I’ve been told about this is based on this friendship. I just hope he wasn’t bullshitting her. I’m tired of thinking about it. Eight hours until show time. Ready?

Real Rob:



Pete was huddled next to the substation that feeds the prison. He had unearthed the junction box housing a simple switch he had installed less than a week ago. Pete was an electrician and knew things. Things like how easy it is to disconnect a 13kV High Voltage supply from a substation to a prison with a remote activated fuse.  Pete had rigged the feed a few nights previous. Cheshire is a sleepy town, so a man with a hard hat poking around a substation at 3 am didn’t attract attention. Plus, the station was off the main road, in a field, 60 yards from the northwest corner of the Cheshire Correctional Facility.

Pete adjusted the frequency and pressed the transmit button, “Bullitt, this is Basher” said with a bad British accent, “Are you in position?” He half whispered like a cop in a surveillance scene. They had given each other “handles” ostensibly to avoid interception. They liked movies and used characters that fit the roles in their real-life production. ‘Banker’ was Rob’s character. 

Bullitt replied, “I’m in the parking lot, ready to move to the alley.”

Basher checked the time, 6:55 pm. “Proceed, Operation Monte Cristo starts in ten minutes. See you in the alley. Love my Bullitt!”

“Love you too Bash. See you in eleven minutes and 30 seconds. Oh, lose the bloody accent!”


Rob stood in the yard, ten-feet from the northwest corner, facing in. Don’t scratch your nuts! He depressed the transmit button through the front of his prison-issued jumpsuit and held it for five seconds.

The lights in the yard went out. Rob’s heart rate went up. The Banker turned around and ran. He didn’t notice the ensuing commotion. He got to the fence and found the board on the first try – holy shit! It slid across the ground as he slinked under the de-electrified fence. Andy Fuckin’ Dufresne! 

He veered 45 degrees to the north and continued. His eyes had adjusted and he saw Pete’s dark figure straight ahead with an open gap in the chain link fence.

Sirens came to life and the floodlights came on. The Banker was at the fence within touching distance of Basher when the voice bellowed “HALT!”

“CUT.” The Director shouted. He moved forward with the stage crew applauding. “Great job guys”

“Do it just like that at the opening tonight and we’ve got ourselves a Broadway hit!

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