Jesse Bailey


There was a woman years ago that I was in love with. It was before prison. It was way back in the late 90’s when we met. We’ll call her “Pumpkin”.

Pumpkin had a boyfriend at the time and was living in an upstairs room in a rundown ratty old house with like 9 other people. She was barely getting by. I remember comming to hang out with her boyfriend and she would tag along. I’m glad because I thought see was cute.

We would go to pool halls, movies and sometimes go camping together. To continue to to hang out and not feel like a third wheel I started dating one of Pumpkins friends. I dated her friend for awhile.

It was a short lived relationship. I just couldn’t do that for to long. That wasn’t me. To string someone along like that under false pretenses. I mean, I didn’t even kiss her that often. I felt like a dick pretending like that. So I broke it off. They both didn’t like me much for dumping her like that. But I should have never started it to begin with. My bad.

Not long after that I got a Motor Cycle. It was assume. First Place I went was over to my buddy and Pumpkin’s place to show it off.

I took both for a ride on the back. He had a great time and told me my bike was so cool.

But Pumpkin, She flipped out the whole time. Screaming the whole ride. She couldn’t stop yelling at me to slow down. She thought she was going to die. I think she hated me more now than she did after I dumped her friend.

She stopped talking to me. When I came over she would give me the silent treatment and stay in the house. That kinda sucked so I just slowly stop showing up and going over there.

About a couple of years went by. I had forgotten all about her. I was still single, but in a lonely state In my life. I was still doing good. I was staying clean, had a job, still living at home with the parents, but was really close to getting my own apartment.

I was sitting shotgun in the car with my mother, leaving Walmart one day. As we were leaving the parking lot driving past the entrance. I caught a glimpse of someone I thought I knew comming out the front doors. But I’m wasn’t sure. she looked familiar, and she was with a little blonde girl about 2yrs old.

I relay all this to mom. I am not sure what to do. My mom pulls over to the curb and says to me, ” If you think its this girl pumpkin than why are you still sitting here in the car. Go see if it is!”

And with that little motherly push, off I went to see if it is really her.

We talk for about for just a 2 or 3 minutes. We say hi, exchange numbers and I am introduced to her beautiful little girl. (Little Pumpkin).

Mom pulls around and I get in. I have good news and bad news. I tell her. The good news is, it was Pumpkin and that was her little girl. The best part is I think I have a date for next weekend.

The bad news is, my bike isn’t going to cut it. She hates motor cycle’s. I don’t think she’ll get on it. So, can I barrow the car? It was kinda your idea to go see her.

Fast foreword now to 2003. We have been dating for several years and things have been going pretty good between us. We both had jobs, our own apartments and I finally got a car to take her places. We were in love. I believe our last step for our relationship was to move in together.

The only thing that was going wrong with me was my addiction. It was getting really bad. I had stopped going to NA meetings. I was using all the time. Work was suffering too.

The only time I was sober was when I was with Pumpkin and her daughter. Or just watching her daughter while Pumpkin was at work . As much as I loved both of them I couldn’t use or sell drugs around them. I didn’t want to corrupt their life with my bullshit.

They might not have realized it, but being with them, I didn’t need or want drugs. In a way they kept me clean even if they didn’t know it. Looking back on it now I probably should have spent more time with them than I did.

I screwed up big time when I started committing armed robberies. The drug world had a grasp on me, and it got out of control. But Pumpkin didn’t know anything about any of that. All that crime was my secret from her. The police didn’t even know it was me. But my time was comming.

I knew my time was running thin and I had to stop with the crime. I quit using drugs. Stopped selling drugs. The biggest thing of it all, was I stopped robbing and got rid of my gun.

I figured I should tell Pumpkin what was going on before she found out some other way.

I took her to a real nice casino. Whined and dined her and bought a few nice things. Played some BlackJack and at the end of the night broke it all down to her. I mean everything.

At first Pumpkin thought I was joking with her. Then she realized it was all real. I was the masked man she had seen on TV they called the “Shoreline Bandit”. It blew her mind.

I told her I loved her with all my heart and if she would marry me. Like any normal, sane person would do, she said “no”. It broke my heart in two, but I totally understood. I wasn’t mad at her decision at all. Just very sad.

Needless to say that’s where the night ended. I had something good going with her and blew it because I got involved with drugs. I told myself this would never happen again. I never wanted to be in this situation again. EVER!

Within the next 6 months, another woman I knew decided to call the cops on me and tell them what I did, and where I was. Within the hour that day I was arrested, at my parents house and taking to jail.

Pumpkin came to see me in county jail a few times. She told me she would wait for me till I got out. I knew it was going away for a long time. I didn’t want her to do that. I told her that she needs to move on with her life and find someone new. Someone that can love her like I do and hold her on a pedestal.

I would like to be her friend and get a letter from her every now and then if that’s what she wants. I would enjoy it too. But you must move on with your life Pumpkin. That would be best.

I think those word were harder to say than they were for her to hear. But in my heart something was telling me….

If you love her, let her go……

We still talk to this day. We are still good friends. She has remarried and had another kid. I am so happy she found love again. I can hardly wait till I am able to do the same thing.

Her daughter has gotten married too. Its hard to believe that little girl I once knew, who was just 7 yrs old and so tiny, is now a woman. I wish I could have been there to see her grow up. To see her walk down the isle. I had always looked at Little Pumpkin as the daughter I never had.

It seems like yesterday I was taking her for her first motorcycle ride when she was 5. Pumpkin hated me for doind that to. The smile, joy and laughter Little pumpkin had on our ride still ring in my ear.

I missed all that, because I decided to pick up that gun.

I am glad their all happy today and still my friends.

Jesse Bailey
DOC #879476

Categories: Jesse Bailey

4 replies »

      • thank you for kind reply. I am a fan. I am a stckler on grammar but I understand as I often have to transcribe Tommy’s mail and “changing it seems like an offense, right? I havent read welcome page.


    • Some story’s I put up like this one are just things that are on my mind. I feel like if share story’s like these people will get to know me better. what type of person I am I my heart and what kinda things I believe in. Just an understanding of what I’m about. -Jesse


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