Timely Tips to Help Trump Tackle Prison | HumorOutcasts

Timely Tips to Help Trump Tackle Prison

December 5, 2017
By

For the holiday season, I have decided to turn over a new leaf and be helpful to Trump. I know; it’s such a departure for me, but as this investigation drones on and his fate takes a bleak turn, I think I can help him make the transition from Leader of the Free World to Leader of Cell Block D. You might say, “What gives you the right to offer counsel on prison life?”  Let the jaws drop, but here it goes: I’ve been in prison—a men’s prison.

Okay, not as a resident or as a fiancé of a felon with conjugal rights, but the state prison was part of my beat as a reporter so I spent some time on the inside. And between you and me, it takes just one lockdown to make you appreciate life on the outside.

So, let’s get on with my Christmas charity before I change my mind. In the not-so-distant future Trump and his family might find themselves—how shall we say it—experiencing an unfortunate period of incarceration, I thought it would be a nice gesture to give them some practical tips on passing the time.

Don’t talk about your Ivy League educations, your mansions in Florida and NYC or your many buildings that required you to evict the elderly and poor so you can live in those mansions in Florida and NYC:  To be blunt, some of those people you evicted are probably sharing shower space with you now.  It’s best just to tell them you lived in a three-bedroom split level on Long Island and let them think you are one of the real people.

Color your hair or better yet, let it go gray:  Donald, that orange-yellow hue on your do, is not a good look for prison. It’s over the top and gets a lot of attention and the last thing you want in prison is to be the center of attention. Try to blend. In fact, that should be your new mantra.

Don’t say the words “Believe me.”  You say these words a lot, but you are a rank amateur in spouting this phrase next to the accomplished criminals you will see day in and day out. If you say “Believe me” and they do, and they find out you lied, you better pray that a few of the prison guards voted for you.

Get used to days with no golf.  While you might not be able to play 18 holes, prisons do have something called “the hole.” Okay, it’s not quite the same as Maralago, but, criminals can’t be choosy about their digs.

If by any chance you can room with Donald Jr. or Eric, you might want to bring up how your boys love to kill big game for the hell of it. Bragging rights on killing innocent animals might give your sons  some serious cred, and while this might not help you initially, it might help them get into the cool prison gang. And if they are in the cool gang, you might be safe by association.

Don’t talk about Billy Bush or anything associated with your womanizing and sexist ways.  Those who are in prison might want to try out your techniques for romantic conquests on you.

Don’t talk how you were the best at anything.  Boasting about your life on the outside will not sit well with the inmate leaders or their loyal followers. Fighting off congress is a piece of cake (which you will rarely eat by the way) next to fighting off a 6’5” convicted murderer who spends his day bench pressing 450 pounds.

Get used to prison food.  This is where the cake comes in. There is not a lot of fun food.  You might get something that looks like KFC, but you will only get one helping. Hey, tax dollars pay for your meals and since you cut prison budgets, you get what you get.

And finally,

It might be helpful to find God.  I heard he lives there.  From my experience talking with inmates, everyone finds him in prison. He might not be thrilled to see you. You have been a dick to the people he cares about most. But he might throw you a pittance of pity. Good luck! Maybe I’ll swing by and visit.

Donna Cavanagh

Donna Cavanagh is founder of HumorOutcasts.com (HO) and the partner publishing company, HumorOutcasts Press which now includes the labels Shorehouse Books and Corner Office Books (HOPress-Shorehousebooks.com). As “den mother” to the more than 100 aspiring and accomplished writers, producers, comics and authors, Cavanagh’s goal is to allow creativity to flow. She is a former journalist who made an unscheduled stop into humor more than 20 years ago. Her syndicated columns helped her gain a national audience when her work landed in the pages of First Magazine and USA Today. She teaches the how-to lessons of humor and publishing at conferences and workshops throughout the country including The Philadelphia Writers’ Conference and Erma Bombeck Writers Workshop. The author of four humor books, Cavanagh hopes her latest book, How to Write and Share Humor: Techniques to Tickle Funny Bones and Win Fans, will encourage writers not only to embrace their humor talents but show them off as well.

More Posts - Website - Twitter - Facebook - Google Plus

Share this Post:

Tags: , , , , , , , , , , , , , , ,

5 Responses to Timely Tips to Help Trump Tackle Prison

  1. Bill Y "The Legend" Ledden
    December 10, 2017 at 7:50 am

    When I was a younger than I am now, I called my boss and told her I couldn’t come in to work because I had manfu (it’s real Don Don’s). I hadn’t got manful but a few weeks later, I did catch it and it wasn’t fun. If karma is real (it’s real Don Don’s) Trump will get his comeuppance and prison sounds like a good place for him to get it.

  2. December 6, 2017 at 6:14 pm

    I think you should let him keep the orange hair. It will match his new outfits.

  3. December 6, 2017 at 9:19 am

    Good advice on the hair color. He’d be such an eyesore with his matching prison clothes. It’s funny, really. We had a black president and now we have an orange one. Sadly, orange really is the new black. Too bad we can’t go back to the dignity and intellect of the black in office instead of the orange imbecile who resides there now.

  4. Bill Spencer
    December 6, 2017 at 6:19 am

    from the White House to the Big House.

    Have you seen his tweets? He NEEDS Corrections.

    Maybe he’ll make a penal tape.

    • December 6, 2017 at 6:27 am

      I blocked him on twitter. I figure if we don’t respond to him only at him, he will eventually go away!



User Login

New Release
How to Write and Share Humor
By Donna Cavanagh Published by HumorOutcasts Press

Available in Paperback and Kindle


New Release
Boomer on the Ledge
By Molly Stevens and HumorOutcasts Press

Available in Paperback and Kindle



New Release
Heartly God?
By Wil 3. and Shorehouse Books

Available in Paperback and Kindle






Archives