“I remember once my father and I were walking down 5th Avenue, and there was a homeless person sitting right outside of Trump Tower. I think I was probably nine or ten…and I remember my father pointing to him and saying, ‘You know, that guy has eight billion dollars more than me,’ because he was in such extreme debt at that point.”

– Ivanka Trump, Born Rich


Dear President Trump,

You’re probably wondering how I’ve been doing all these years. On that long-ago afternoon outside Trump Tower, when you used me for a teachable moment with your young daughter, I’m sure neither of us could have predicted where we’d be today: you, the most powerful man in the world, and me, sitting in the same spot outside your building in my urine-soaked pants, expecting Secret Service agents to run me off at any moment.

I went from being $8 billion richer than you to being more than $30 billion poorer. What the hell happened?

I toss and turn on my bench in Central Park at night, asking myself how someone squanders $8 billion. I never took cabs, I took most of my meals at soup kitchens, and yet…it’s all gone, every last dime! My overhead was very low, which is no mean feat in Manhattan. Still, as I watched you pull yourself up by your bootstraps, regain your wealth and eventually surpass even your previous successes, I hemorrhaged billions each year at taxpayers’ expense until I ended up with nothing. Nothing!

Anyone else in my position would have at least $12 billion socked away by now, but I’m embarrassed to say that at the end of a long shift cleaning my clients’ windshields at a nearby intersection, I’m lucky to have enough cash left over after operating costs for a couple of cigarettes and a 7-11 frozen burrito. Look, I know I have no one to blame but myself. Plenty of third generation fetal alcohol syndrome/crack babies grow up to earn Ivy League business degrees and build real-estate empires — just not this guy.

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When things got really tough, I consoled myself with the knowledge that, after you’d hit bottom and started to get your life back together, that beautiful little girl of yours didn’t have to miss a single Aspen ski trip, or cross the threshold of a school with the letters P.S. in its name. If I was feeling a little sorry for myself because someone had stolen my shoes again, or that suppurating sore on my face was taking so long to heal, I imagined you opening your mail and finding nothing but letters from greedy creditors and I thought, “If he could come through that, then who am I to complain about my little problems?”

Don’t get me wrong — it hasn’t all been miserable. There was that time I spent five luxurious nights in a private room at Beth Israel after contracting a highly contagious strain of penicillin-resistant tuberculosis. Great views of the city, sponge baths twice a day, and the Mandarin orange jello wasn’t half bad! But I knew it couldn’t last.

And while I never received the accolades befitting a great man such as yourself, I was once singled out by the ER staff at Mt. Sinai for being the patient with the most near-death experiences in one month. They gave me a nice going-away goodie bag stuffed with toiletries that I was able to exchange for a single dose of street heroin that, just my luck, landed me back in the hospital as an OD victim the following night!

I may not always have had your good fortune, Sir, but I’ve had my share of $2 lottery ticket payouts, and I once won a gorgeous, lightly-worn Burberry in the Salvation Army overcoat drive. Unfortunately, my prize was removed from my body as I lay passed out in the Bowery a few nights later, but hey, easy come, easy go, right, Mr. Trump?

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When the stresses of outdoor living caused me to act out, screaming obscenities and flinging my feces at passersby, I was sometimes given a short respite in county jail where, after being sodomized by my cellmates, I was free to nurse my chilblains and enjoy “three hots and a cot.”

It was during one of these stays that I first learned you were running for President. Pointing at your image on the TV screen in the day room, much like you had pointed at me outside Trump Tower, I recounted how you had once expressed envy of my debt-free lifestyle. My fellow inmates didn’t believe me, calling me a crazy old bum and yelling at me to shut the fuck up, but you can bet I had the last laugh when Ivanka shared our story on national television at the Republican Convention for all the world to hear, as an example of your terrific parenting skills.

When you won your party’s nomination, no one could have been prouder than me. And as the election rolled around, I would have voted for you in a heartbeat if I’d had a permanent address and didn’t have those felony drug convictions on my record. I wanted so much to attend your inauguration, but unfortunately I had a delousing appointment that day.

Now that you have assumed office, I eagerly await the new job you have lined up for me — hopefully something that allows me to apply my exceptional panhandling skills — perhaps as an investment banker or hedge fund manager?  Please know that I am rooting for you every step of the way, Mr. President, as together we make America great again!

Respectfully yours,

Ronald “Brother, can you spare a billion?” Smith
Sidewalk, Trump Tower, NY, NY

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