The I-Team obtained a copy of the letter, which reads like a sob story from a solitary man.
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The kingpin and imprisoned ex-boss of the notorious Sinaloa Cartel hand addressed the envelope and affixed a pair of American Purple Heart stamps to ensure delivery from the supermax prison in Colorado to a federal court in New York.
By himself, in solitary confinement as he is required to spend most of every day, El Chapo has a lot of time to write letters including a recent one to Brian Cogan, University of Illinois graduate and senior judge now in the Eastern District of New York.
READ MORE: Emma Coronel, wife of drug lord El Chapo, faces exceptional new monitoring by feds
The ruthless and unforgiving narco-king begins the letter apologetically.
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"Sorry to bother you again," he writes to the judge after having penned previous letters asking for the same perks: to see his wife, Emma Coronel, the former beauty queen, now residing in California.
"I ask that you please authorize her to visit me and to bring my daughters to visit me, since my daughters can only visit me when they are on school break, since they are studying in Mexico," he writes.
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"He certainly thinks he has a shot. That's why he's trying-the attitude is when you're in that kind of circumstances he's in what's the harm in trying so he's trying and trying and trying again and again," said chief ABC7 Legal Analyst Gil Soffer.
The 67-year-old also wants something else while he's locked up: better phone privileges.
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"I also bother you to continue giving me the two 15-minute calls a month" that the druglord claims Judge Cogan previously afforded him. As in the past, the judge wasted no time reminding Chapo it's not a call for the court, it's a Bureau of Prisons decision.
"The court may say, as courts sometimes do with litigants who are constantly bringing lawsuits that are frivolous, may say I won't take any more letters. The Bureau of Prisons might also be able to say, you can't send any more letters. So the time will come when he simply can't," said Soffer.
Soffer added that federal prison officials and U.S. law enforcement will keep El Chapo under such extraordinary security measures until there is no longer a possibility that he will try to run the Sinaloa cartel from behind bars.
And there is another concern: escape. He's done it before, tunneling out of a Mexican prison and then escaping by motorcycles.
Nobody has escaped from the supermax.