Robert Maday was already a convicted bank robber when he escaped from custody while being driven to court by two Cook County state's attorney investigators in 2009.
Maday, 42, overpowered the agents, grabbed their guns and forced one of them to give up his pants before he escaped. Maday then went on a 27-hour crime spree in Chicago's suburbs while being hunted by authorities. He used the guns to commit two separate carjackings against two women before robbing a bank.
He was found guilty on Wednesday of all five escape, bank robbery and weapons counts.
Maday wrote a detailed letter to his girlfriend after he was re-captured about his "elaborate" escape plan that had been foiled before he made it out of the state.
"What does one say to the person you love most at the end of yet another failure?" he wrote in the letter to his girlfriend Lisa Barruzza. "I had a plan so thorough, so elaborate, so enticing, so...I won't tease you with it now."
He even referenced a bank that he robbed while on the lam.
"Got my getaway $ Friday (20 hours behind schedule) from a vault in Bloomingdale!" he wrote. "All I needed was a car that wasn't being looked for by an army."
Maday told the bank teller that he had a gun, but the gun is never seen in surveillance video. His attorneys hoped that the question of whether he had a gun might help him avoid a charge on the using a gun during a robbery count, but it did not.
"We thought there was a real question on whether he did have a gun when the bank was robbed," Maday's attorney Anthony Sassan told reporters after the verdict, according to . "We were confident as we could have been that they would come back with a non-guilty on that."
The manhunt resulted in a high-speed car chase, crash and his arrest.
"I only needed to step foot out of Illinois; got beyond the reach of the hunt that was underway," Maday wrote in the letter. "I tried darling. I gave it my best attempt."
Prosecutors said Maday's own written words helped convict him, according to WLS-TV.
"He was telling numerous people he came into contact with that he was the escapee on the run," assistant U.S. attorney Annie Kastanek told reporters after the verdict,"He seemed to think in his own mind that he was this legendary criminal."
In addition to the federal convictions, Maday already faces 43 years in state prison for previous crimes and the carjackings during his time on the run, according to WLS-TV.
Maday was aware in his letter that he would not be a free man for a long time, if ever.
"I'm sorry if you were humiliated by me Lisa," he wrote. "Forgive me please. For everything. For hurting you like I have. I will be an old man when I come home. 58, 60, 62, 70. I almost succeeded Lisa. Please remember that. I was really close."
In the margin of the letter, he asked Lisa to send him $100 to help him in jail.