Home Editorials Dear Arkansas…

Dear Arkansas…


Dear Arkansas,

It has recently come to my attention that an old friend is running for office in the Natural State. And I’d like to object.

Back in 2010, I was an active volunteer on a local gubernatorial campaign. Fresh off of Governor Palin’s bout of office-quitting, the opportunity for a change in the governor’s mansion seemed excitingly attainable. It ended up being anything but. However, that summer was filled with hope and enthusiasm. It was nice.

One of the many people my wife, Heather, and I met over that summer was an energetic, slightly awkward campaign manager with a great sense of humor and zero recognition of personal space. His name was Caleb Pritt. He had just been hired by Lieutenant Governor candidate Dianne Benson, who was a heavy favorite competing in a slightly contested primary for the spot on the Democratic ticket.

caleb chris john at bobs

I first met Pritt in May of 2010, on the flight from Anchorage to Sitka for the state Democratic Party convention. He really didn’t like to fly. I shared the disdain for being hurled through the air at 40,000 feet. We hit it off.

That summer, we grew close. He helped us move into our first home. We spent many nights in our backyard over a fire, enjoying drinks and laughing about the ridiculousness of Alaska politics. Sometimes he didn’t last too long into those nights.

Heather and Johns House 275

By the winter, that friendship ended coldly.

Things my wife and I had told Caleb in protected confidence started coming back to us. Nothing too damning – anyone who knows me can tell you I’m fairly outspoken and transparent. But when you tell someone something in confidence, you don’t expect to hear it from strangers the following day.

Friends of ours, including our roommate, let us know that Caleb had borrowed hundreds of dollars, and not bothered to repay a penny.

And then he wrote an editorial for the Anchorage Press about a good friend of mine, named Roger, who had passed away unexpectedly. Caleb barely knew him, and the capacity in which he did know him was primarily one in which he was compensated for, as a campaign manager.

He made up half of the article. He described someone who didn’t exist. I took issue.

When I objected to him, privately, he told me he was assigned the story. I was also writing for that paper at the time, and we shared an editor, so I asked if that was true.

The response: “Nope, he asked me if he could write that.”

When I pressed the issue with Caleb, he told me that my deceased friend would be ashamed of me.

I snowplowed my entire street that day. I’m still pissed off.

Caleb never settled the debts with my friends, who eventually gave up trying to collect. Last I talked to Caleb, he told me he wanted to repay them, but was “financially in a very precarious position[.]”

Apparently, that position got worse.

Six months later, Caleb threw a fundraiser for the son of his previous employer, Dianne Benson. Latseen Benson is a soft spoken Iraq War veteran who lost both his legs to a roadside bomb in 2005.

As Bent Alaska documented at the time:

A fundraiser comprising drag queens and LGBT youth at Mad Myrna’s in Anchorage on Saturday night netted over $3K+ for a severely wounded Alaska veteran to help build him a handi-capable/handi-accessible home.

Event organizer Caleb Pritt was pleased with the result.

A lot of really good people who I’m really proud to know worked tirelessly to make that fundraiser a wild success. But the money never made it to Latseen, and Caleb skipped town, returning to his home state of Arkansas.

Then, last night, I saw this news report:

[Someone] running for political office in central Arkansas has a past some folks from out of state want you to know about. Drew Pritt wants to be the next justice of the peace representing the 9th District of Pulaski County. But… there are some folks in Alaska questioning his integrity.

Excuse me?

And there he was, from this obscure news report from Arkansas, three years later, running for office? Drew Pritt (who also has gone by A. Caleb Pritt, Andrew Pritt, Diedra, Diedra Windsor Walker, Diedra Richards, Diedra Richards Ho Jenkins, Diedra Richards Harrison, and – as I knew him – Caleb) looked into the local reporter’s eyes and said: “I didn’t steal money from the veteran, didn’t pocket, didn’t abscond, didn’t take off.”

He says he has no idea what happened to the money. He also somehow forgot the name of Latseen, the son of the candidate he worked for; who was often on the campaign trail cheering his mother on. Pritt referred to him only as “the veteran.”

So, once again…

Dear Arkansas,

Please don’t afford this man one single damned vote. He is everything that is wrong with everything, only worse. And then some. Times ten. Turned up to eleven. If you see him, I would ask that you encourage him to come back up north. Police still have questions. I still want answers.


  1. Andrew Pritt is from Warren Arkansas, He never could get any votes here, we all know him and what he is. He cons people, but he will finely show his true colors.

  2. As a young man in high school, he worked for me with our tomoto harvest. He didnt want to work in the shed, where he was needed, he tried many times to get me to let him work in my office. When i refused he became highly upset. I always thought he was looking for a way to get into my banking business. After reading this, thank God i didnt allow him in my office. None of this surprises me.

  3. If I am not mistaken we was in some hot water before this for something kind of like this I before… I had a few political science courses with him and he is personally likeable but there is that vibe I got not to fully trust him.

  4. As a classmate of his for years at Hermitage High School in Hermitage, AR. I can assure you, the boy is “touched”.

  5. To this day I cannot believe that he had such a lack of integrity to steal from a Wounded Warrior. And just as much I cannot believe that he would be running for a publicoffice given the trail tht he has left behind. Some people do not seem to have much of a conscience.

  6. He invited himself to spend Thanksgiving with my family 10 plus years ago. Pushed his way into my family, that is always very giving. During the few days here he managed to steal my sweet grandmothers bank info and take hundreds of dollars, running away to Washington D.C. He tried to convince us it was all a misunderstanding!

  7. Dear Alaska: We don’t have to be told. We are all aware of “DREW”. Not to worry he never got any votes here anyway. We would be more then happy to send him back your way.

      • If he does come back though he will end up in jail. I am one of the people he ripped off; over $500.00 and my laptop with my school work for my graduate program on it. I will so press charges.

    • The reason we feel the need to say something is because we know how manipulative he is, especially to the youth who do not know the back story. He still hasn’t even filed for Justice of the Peace but according to his Rally.org site he has gotten over $700 in campaign contributions from 72 people. https://rally.org/DrewPrittJP6

  8. He’s been arrested here a few times for hot checks. I really wish the Feds would look into his case. I looked him up on Google by his drag name of Diedra and I’m still having nightmares about what I saw. He’s truly a P.O.S.

  9. He’s a typical liberal democrat…He is a scam artist,has never worked,always finding a way to scam people into buying into his gimmicks. Hope this lying,homosexual,cross dressing,weasel gets what’s coming to him.

      • Thank you John for setting William straight in a respectful manner (not sure I would have been as generous), which is always the best policy in these manners.

  10. Andrew is just bitter that he could not make it in Arkansas. Arkansans were too smart to fall for all his deception.

  11. Just thought you’d like to see what he says about your piece here. Notice he refers to you as “some blogger”. 🙂

    Drew Pritt shared a link.
    February 16 near Little Rock, AR
    This has been a hard week for me. I have coped with losing a lot but I realize everyday is a new day. Before I go to sleep, for my true friends who have helped me overcome a lot this week, I want to thank you. I have had someone dredge up something that was found to be untrue years ago and act like it’s news. And many of you probably saw the editorial some blogger wrote called Dear Arkansas. I have coped with death this week and also the end of a short lived relationship.

    BUT I am alive. I have my health somewhat. I have a new job I start in the morning. I have a roof over my head, food to eat, two wonderful pets, and lots of special people in my life. I can’t complain. Thank you for standing by me, checking up on me, calling some out on spreading gossip, or genuinely checking on me. I am blessed because of those of you who are true in my life.

    Mind you, I keep DREW PRITT on my Facebook friend list solely to keep an eye on him, and because he is like watching a train wreck. He has been making posts asking people for donations for his campaign. I keep checking the page tracking his donations and it hasn’t made it past $25 thank goodness. I planned on intervening if it looked like he was indeed going to receive substantial donations. I’m not sure why I ever thought that was a possibility.

    Also, I think it’s funny that he mentioned your blog because although I hadn’t seen it before, I HAVE NOW that he posted about it! Thanks, Drew!

  12. I should have formed my comment post better…the quote from his Facebook quote ends at “true in my life”. 🙂

  13. Oh, and this too:

    Drew Pritt
    February 16 near Wiederkehr Village, AR
    Recently some have shared an editorial with someone who is biased against me with an agenda to harm me. So they lied. And people have spread this thinking the Alaska Commons editorial is truth. It is not and I have been advised for three years to ignore it. No charges filed, no credible evidence, just a small group of ppl manipulating social media to settle a score or use me as a scape goat. If you truly are my friend as many you stand by me. If you want to gossip just imagine the pain and frustration if you were the one going through what I have. This is all the attention I will give this manufactured drama and attempt to bully me with a lie. No more explanation or comments.

  14. I’m not sure if this will help at all or not but when he skipped town he also took off with my $450 apartment deposit as well as $500 of my roommate’s rental deposit. My roommates $600 laptop, and sold ALL of his roommates at the times furniture for cash and dash, and took who knows what else of theirs for personal consumption and use!

    Caleb was supposed to be helping my roommate and I secure an apartment in the building he lived in with another of my friends and his boyfriend, and played mediator between us and the landlord. Thank God we hand delivered our first months rent, because he would have gotten that too! (Caleb was not my idea, by the way, NEVER liked the guy, I was subleasing from my roommate and gave her the cash.)

  15. Drew also stated on his Facebook page, at the time of the incident, that he was responsible for the missing cash as organizer of the event, though he denied culpability. He said he would repay it because he was the organizer and ultimately responsible for the money not making it to Latseen. Once he returned back here to Arkansas, however, he immediately began entering drag pageants as Diedra (as late as last year) spending hundreds of dollars for each pageant to compete for crowns he could NEVER win, when Latseen or “that Veteran,” goes without the $3,000 he stole. This is the kind of thief, conniving, horrible, sick, person that we Arkansans have to continue to deal with. Thank you for the warning, but it really wasn’t necessary. We know all too well who Drew is. He will waste his money for the rest of his life trying to seek public office, but he will NEVER succeed in this state. There are far too many of us that will NOT allow him to succeed. I’m a proud gay man and I’m deeply ashamed of Drew. He does NOT represent our community. He should be in prison as I think this crime deserves justice.

  16. I am shocked at the many, many lies that are told here. I guess it’s true what they say, that when people get behind a computer screen they can say whatever they like and act like it’s the truth. No, I never invited myself into someone’s Thanksgiving and stole money. No, I have not skipped out or lived with a “boyfriend”. No have I not done all the things here said about me. Mr. Walsh I do not know you nor do I care to know. I never worked or tried to work in an office in tomatoes.

    FOR THE RECORD, John Arrono you bastardize the First Amendment to spread lies.

    There is no evidence of the lies you spread. There’s no conviction, not even a lawsuit and court case. So keep on lying. At the end of time all of us will stand before God. I have a clear conscience. You all need to get right with God.

    But in the meantime, leave my name out of your mouths and get a life. Because the only life you possess is of liars and gossips.

    • If you have done nothing wrong as you state why not return to Alaska and answer the many who have questions about the missing money that you have publicly admitted you were responsible for. Would you like the Facebook screenshots where you promised to pay Latseen back? Another Drew Pritt lie. You stole the money stop playing games. Oh, and you’re the one hiding behind a computer except when you’re stomping squirrels to death.