WHINE WEDNESDAY PRESENTS: THE WHINIES
Welcome to the final edition of Whine Wednesday with Derrick Van Orden, America’s fiercest keyboard warrior. We comb through the hundreds of tweets DVO posts during a week so you don’t have to. Grab a glass and join us one last time for Whine Wednesday!
MADISON, Wis. — Unfortunately, all good things must come to an end, and Whine Wednesday is no different. This cycle, our editorial team has sorted through over 12,000 Tweets from Derrick Van Orden—and that is just our rough estimate, we seriously lost track after at least that many Tweets.
Election day is next Tuesday and to close out the cycle we wanted to reminisce on all of the fun we’ve had with Van Orden’s online activity, so welcome to the Whinies! We have combed through Van Orden’s Tweets for what we can only hope is the last time, and are presenting the most out-of-pocket, head-turning, and just flat out bizarre Tweets from Van Orden over the past two years. So for one last time, grab a glass and join us for the Whinies!
DVO’S DADDY OF THE YEAR
And the Whinie goes to….DONALD TRUMP
If you are a frequent Whine Wednesday reader, it should come as no surprise that Donald Trump has been crowned Derrick Van Orden’s Daddy of the Year by our editorial team. Truly, how is Trump going to replace Van Orden? No one else sucks up to him the way Van Orden does. Here is our favorite Trump/Van Orden moment of the cycle:
We can’t believe we are writing this, but we truly understand President Trump here. We also find Van Orden incredibly annoying and try our best to ignore him. We’ve got some good news for the President: Hopefully by this time next week, we’ll have a new representative in the Third Congressional District and we can all move on and heal from Van Orden’s tenure.
We’d also like to take a moment to recognize our other nominees:
Pete Hegseth: At least when Van Orden loses, him and Hegseth will have more time to talk about alpha males and testosterone together <3 (but also, gross).
Elon Musk: For funding Van Orden’s reelection campaign and perhaps being the only person who needs to touch grass more than Van Orden.
Misc. Trump Officials: Seriously, how many more b-string officials do they have? We swear they invent a new one every time Van Orden’s campaign needs a little boost.
FAV AI SLOP MOMENT
And the Whinie goes to….Van Orden fantasizing about himself on the beach with buff men
Unfortunately for literally everyone, this cycle Van Orden has discovered how to use AI. There were so many AI slop moments from this year, it was hard to pick our favorite from Van Orden, but nonetheless, a decision has been made. Our favorite AI slop moment goes to Derrick Van Orden generating an image of him picking weeds on the beach with a bunch of buff men working out behind him.
There is an age where yard work becomes workout.
I am now that age. pic.twitter.com/vC5iDkb6ww
— Derrick Van Orden (@derrickvanorden) May 10, 2026
Yeah, and we are still unsure as to why he is picking weeds on the beach.
MOST OUT-OF-POCKET MOMENT
And the Whinie goes to… “Vollenteer”-ing for a firing squad
Listen, it’s really hard to pick just one out-of-pocket moment from Van Orden this cycle, but volunteering to be a part of a firing squad late at night with a typo-riddled tweet is a perfect summary of the way he has operated in office. Reckless, sloppy, and absurd.
.Vollenteer https://t.co/l8tVx5daWc
— Derrick Van Orden (@derrickvanorden) October 6, 2026
UNDERRATED MOMENT OF THE YEAR
And the Whinie goes to … Van Orden gets caught interacting with OnlyFans model on main!
Something these Whine Wednesday editors feel didn’t get enough attention was earlier this year when Van Orden tweeted at an OnlyFans model, recommending she try Culver’s.
Listen, we get it, Culver’s is great! Quick question though, why is an OnlyFans model popping up on Van Orden’s feed and why does he feel the need to respond to her about Culver’s when he won’t even show up for his own constituents?
BEST TYPO
And the Whinie goes to … Long wanks in the woods
Perhaps the fan favorite of our Whine Wednesday editor’s picks for the Whinies is when Van Orden told WisDems Chair Devin Remiker that he enjoys “long wanks in the woods.”
Van Orden brushed this off as a typo, which we find a little hard to believe. Never has this Whine Wednesday editor ever had the word “walk” autocorrect to “wank” while typing. Perhaps this reveals a little bit more about Van Orden’s online activity.
IN MEMORIUM
The infamous deleted “YES!” Tweet
No award ceremony would be complete without acknowledging those who are no longer with us, and the Whinies are no different. This cycle, we are honoring perhaps the defining Tweet of Van Orden’s career: the deleted “YES!” Tweet.
Are we allowed to say thank you to Derrick for posting? We don’t know if anyone has ever said the quiet part outloud quite like this before.
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