B'ham, Ala.
Jefferson County Jail
July 18, 1936
Listen Anna
This is a matter of business no fun. Now listen you realize how long I have been cut off from my pleasure dont you? And you realize it had on me don't you? Especially me being a young man. An you or any one else should have sympathy and feeling for me. Now listen please dont get offended over what I am fixing to say in your present. I am almost crazy in this place. This is what I want to say its a new warden here at night and he will let me to a woman for all night for $5.00 which it is worth it. I know its worth $5.00 of mine. Because if I dont get to a woman it will soon run poor me crazy. I really have stood it long as I can. I just got to get to one. I have been in jail over five years. And its a shame. Now Anna please send me $5.00 and take your out of my eight. Now please send it rite away I am looking for it Friday. And I will appreciate that the very highwst. Now since I have explain the situation to you. I am sure you will feel my sympathy. Want you? Sure you will! I am looking for it Friday without a fail. Please give my regard to all.
Yours very truly
Olen Montgomery
Please answer soon
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B'ham, Ala
Jefferson County Jail
Oct. 2nd 1936
Dear Anna
I rec'd today my money which I accepted and highly appreciated. I also rec'd a letter from you Wensday telling me about the shoes. Listen Anna I dont want any one old clothes and shoes. And I really need soome shoes and I want them quick as I can get them.
Anna, I am honest and you know that I am always willing and glad to help my own self as much as I can. You already know that. i cant get me no shoes out of the money I got today. Because there is other things I need and must get. Take $5.00 out of my next allowance and get me a pair of Friendly Five Shoes size 7-1/2 real keen toes with a plain cap across the toe and color real light tan. And leather heels. Now Anna get them just like I have told you and I will be satisfied with them. Those are the kind shoes I usual wear. They are conforable wearing shoes. And just send me $3.00 when it falls due the 28th. Now send them just as soion as you get this letter. I need them. And I will appreciate it. I am well in health only my eye gives me a little trouble at time. When is the case comeing up? I would like to know I want to be tried. I had a letter from my mother today. She is all worried and upset about me. I feel so sorry for my poor mother she needs my help and I know it.
Oh well give my regard to all so I will close yours very truly.
Olen Montgomery