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


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