By Jay Bullock Special to Published Dec 14, 2016 at 3:16 PM

The opinions expressed in this piece do not necessarily reflect the opinions of, its advertisers or editorial staff.

Through a surprise "reply all" error, we here at OnMilwaukee were accidentally emailed a trove of letters to Santa Claus. We have sorted through them, like WikiLeaks, and have selected several to publish. Consider it our present to you, readers!


Brooklyn, New York
Oct. 25, 2016

Dear Santa,

I know that next week is Halloween, so it seems awfully early to send this year's wish list. But you know me, Santa – I've always been a planner!

I have tried to be good this year, Santa; I truly have. It hasn't been easy; breaking barriers never is, and you know that I have broken many! I have been sorely tempted to say things and have things done in my name, but I resisted.

The night I clinched the nomination after such a long and bitter fight, I thought for sure there was nothing else I could wish for. Well, besides that one thing, but I hardly have to wish for that, huh? Thank you, Nate Silver!

So my list is pretty simple: Please bring me a Democratic U.S. Senate to confirm my appointments and block the Crazy Caucus in the House. Also, a lump of coal or two for Jason Chaffetz would be great.

I would also appreciate some clear, beautiful weather in Washington, DC, on January 20. I want the pictures in the history books to look as good as I have always imagined them to be.

Until next year, your best girl,
HR Clinton


Janesville, Wisconsin
Nov. 21, 2016

Dear Santa,

First, let me remind you that I have been a good boy. Just look at my blue eyes. How could these blue eyes do anything wrong?

Second, I am relieved. I had been worried that I would not have a good Christmas this year. Boy, was I wrong! In fact, my original wish list – which you may remember I submitted in July as a 700-page bullet-pointed document, "An American Christmas Wish: Restoring Hope While Making Hard Choices," with four thorough appendices and Ayn Rand epigraphs heading each section – may now be discarded.

Attached, please find my new Christmas 2016 wish list. It is entitled "A Conservative Christmas Carol: Rebuilding the Path to Prosperous Titans of American Wealth and Majesty." It is now nearly 1,200 pages, but given your propensity for reading and digesting hundreds of millions of Christmas letters and delivering to as many houses in just a matter of hours, I trust that you can handle such a "curve ball," as my "Be Relatable With Sports Metaphors" booklet (Christmas 1990 – I remember!) would say.

If the full list is impossible this year, you may hold the sections called "Bless the Poor with Bootstraps, not Food Stamps," "I'm Sorry to Hear About Justice Ginsberg" and "Every Womb an American Womb" for Christmas 2017.

God bless you, sir!
Paul Ryan


The Kremlin, Moscow, Russia
Nov. 16, 2016

Dearest Comrade Claus,

Much respect to you from the Motherland! You have granted last year's requests to the fullest degree. Your assistance has not gone unnoticed, my brother. Many town squares in conquered lands will be named in your honor!

Know that I and the whole of the Motherland have been very, very good, Comrade. When the West was ashamed to stand up to the terrorists in Syria, Mother Russia has fearlessly attacked! The bear has been re-awakened, my friend, and we will not sleep again!

This year, I ask for you to remind the world why, Comrade, you wear glorious red. I ask that you lift the Motherland to its rightful place atop the world. Grant me a reunification of the former Soviet glory and bend the will of the world to me. Give to my great American friends the wisdom to accede to any and all of my demands.

Also, bring to Jill Stein a major-label record contract; we in Russia, too, have grown weary of her political career and do not wish her to return to Moscow unless she is opening for that adorable Taylor Swift. Which reminds me – I would also like a Taylor Swift concert in Red Square.

Do svidaniya!
Vladi P


Brooklyn, New York
Oct. 30, 2016

Dear Santa,

Ha, ha. Very funny. You know I always get kind of twitchy around Halloween – too much talk of witched – so you have given James Comey his Christmas wish early as a way to test me! And by funny, I mean, not funny.

Is this because of the "basket of deplorables" thing? I assure you, it was a complete accident that I slipped and revealed the name of what was supposed to be the hot toy this year. I have already apologized to both Mattel and the Elfsters Local 1-North Pole, who took a hit from my spoiling the surprise. I didn't mean to hurt anyone.

In light of all of this, let me revise my previous wish list: A Democratic Senate would still be great, but I would trade it in a heartbeat for Anthony Weiner to be run over by your reindeer. And not in a cute, kitschy way, like in that song, but in a they-have-to-use-dental-records kind of a way.

Still love you, big guy. See you soon,
HR Clinton


Baltimore, Maryland
Nov. 24, 2016

Dear Mr. Claus,

That thing I said about not wanting a cabinet position? I lied. I know I shouldn't have, Santa, but I couldn't help it. I have an image as a quiet humble man to uphold. Other than that, I think I've been a good boy. No knives in belt buckles, no more lies about Mannatech.

So, Santa, if you could, please bring me a cabinet post for Christmas. Surgeon General seems like a great fit if you can swing that, but I would take anything.

Also, can you bring a new painting of Jesus that doesn't look like a Klingon? Thank you.

Ben C.


0230 Hours, Nov. 9, 2016
To: S. Claus
From: The White House
Re: Christmas List

I am writing somewhat early this year, as I have just learned some very dispiriting news. I was hoping my spotless record this year would be rewarded better than this, but here we are. I have some difficult days ahead.

I know that for the last eight years, my Christmas wish has been just one simple thing – world peace – and you always leave me a single cigarette and a note explaining how you cannot make everyone happy every year, it breaks your heart and you know I understand because of what I endured throughout the year. This despite the insanely good cookies from the White House kitchen every year! But I still believe, Santa, I really do.

So let's be clear: That wish is more urgent now than ever before. The world stage is set for a cataclysmic disaster. Political tensions are high, much of the world has not seen recovery from the Great Recession, dangerous madmen occupy leadership positions all over the world. Please, Santa, for the sake of humanity, keep the world safe for the next four years.

If it should happen that I wake Christmas morning to find a lone Marlboro Red and another note from you, I do not know what I will do. I have always found the strength before; this year, I am not so sure.

And no, Santa, I do not wish for some consolation prize like 2009-era approval ratings. My legacy is nothing if it is wiped out by an unqualified egomaniac and his enablers.

Also, Bo and Sunny say hello, and they would love some more of those liver treats.


Grand Rapids, Michigan
Dec. 9, 2016

Dearest Santa,

I do not believe in you, or in any other Godless creatures like the Easter Bunny, the tooth fairly or lesbians.

But I have been asked to write anyway, as I have been hired by a man-child who, though I have great respect for the purpose he has been Chosen for, nonetheless insists on many questionable practices, such as Twitter and something called "Taco Tuesday."

So, if you are real, please bring me the end of public education as we know it. Let Free Enterprise and the Marketplace rise and fulfill His divine purpose.

If you are not real, God forgive me this fiction.

Yours in Him,
Betsy DeVos


Chappaqua, New York
Dec. 11, 2016

Dear Santa,


Can I at least get another grandchild?


Jay Bullock Special to
Jay Bullock is a high school English teacher in Milwaukee, columnist for the Bay View Compass, singer-songwriter and occasional improv comedian.