This Week’s Keith Olbermann Award for Cranky Pathetic Unemployed Whiner Wuss Boy

Certain people can be so predictably tiresome.

In honor of that weary trait, I am presenting an award named for the always tedious, needfully ‘look at me,’ perpetually unhinged, eternally disgruntled, and forever outraged Keith Olbermann, who has never once missed an obvious chance to keep his fat trap snapped shut and pretend he was an adult.

Now, this wasn’t an easy choice by any means – the competition was stiff and as thick as Sherwood Forest. But one enterprising whiner rose above it to shine beyond all the other contenders in a packed field of true professionals and days full of missteps, gaffes, and stumbles.

This week, one tiny, non-binary statuette of pre-tariff Chinese origin with a big bald head goes to?

MATTHEW DOWD

Congratulations, dweeb. My goodness – you earned this.

Let me tell you all about the selection process.

Now, you’re probably thinking I’m giving it to the former political consultant and MSNBC regular for his comments as the Charlie Kirk assassination tragedy was unfolding.

Nah. Ed and David both covered that beautifully, as you’d expect and as it happened – both Dowd fatefully running his jibs and MSNBC first tepidly apologizing, then realizing it wasn’t going to fly, so they canned him.

MSNBC President: Sorry About Slagging Charlie Kirk After His Murder, or Something

Good enough? Not hardly. 

David wrote earlier about MSNBC’s coverage of the assassination of our Salem colleague Charlie Kirk, who had just begun engaging a large college crowd about politics and values when he was shot to death. Matthew Dowd in particular didn’t even wait for the evidence to emerge before castigating Kirk as a “divisive” figure, implying that he got what was coming to him…

Ah. It’s the aftermath of the firing that’s been so sad.

Dowd went on a pity party tour of old friends who would still open the door to him and wound up on [INSERT: barf emoji] Katie Couric’s podcast to wax and whine about getting the hook, over-explaining, rehashing, and parsing that last fatal few moments of his career before he blew it up.

You know – how you relive an argument hours later and always win because all the lines you wish you’d said come into your head like magic?

Yeah. Like that.

 

Couric looks riveted (I jest, I jest), but she’s certainly more impressed with Dowd’s reworked tale of woe that Bill Maher was discussing it on his show later.

Maher wasn’t having ANY of the new, improved version of ‘what I said/meant/wished had come out my mouth/WAAH.’

[NSFW Maher language warning.]

Bill Maher issues a blunt response to the MSNBC pundit who blamed Charlie Kirk’s death on himself.

MATTHEW DOWD: “You can’t be saying these awful words and then not expect awful actions to take place.”

MAHER: “Yes, you can! I do not expect awful actions to take place. I think… pic.twitter.com/rYtNjJHyBZ

— Vigilant Fox 🦊 (@VigilantFox) September 20, 2025

…MAHER: “Yes, you can! I do not expect awful actions to take place. I think this is awful. When you open this window, like, ‘I didn’t like what he said, and what he said was vile, and this and that.’ Irrelevant! Irrelevant. We don’t shoot people in this country, and we don’t defend it, and we don’t mock their death.”

WOOF

So that was bad. Mortifying, I would normally say, but what happened next was, I believe, even worse if someone had any self-respect at all.

During that same excruciating podcast, Matthew Dowd began whining about the Jimmy Kimmel fuss.

Not because of the First Amendment. Not because Kimmel was a friend and Dowd wanted to take a stand.

Matthew Dowd was bitching about Jimmy Kimmel because no one was paying any attention to him.

WHAT ABOUT ME, WAAAAH?!!!!

…“All the shows are talking about how this is awful for America that Jimmy Kimmel was indefinitely suspended,” Dowd said. “And isn’t this awful for America and it’s a chilling thing for the First Amendment? They’re saying that on every platform. Not one person has said anything about me.”

“They’ve all gone out of their way to say, ‘Isn’t this horrible what happened to Jimmy Kimmel?’ — even including Morning Joe [Scarborough] and Mika [Brzezinski], who went after me after the show, basically saying they were glad I was terminated,” he continued. “And now today they’re talking about how awful it is for our country that somebody like Jimmy Kimmel can’t say what he said and he is indefinitely suspended. And not an iota about what their employer just did to another employee.”

NOBODY LOVES ME

“For the last 24 hours, all the shows are talking about how this is awful for America, that Jimmy Kimmel was indefinitely suspended,” Dowd said. “Not one person has said anything about me!”

Find more details and links to related items – https://t.co/I6z5KGDPDP

— RCP Video (@rcpvideo) September 19, 2025

This is an Olbermann moment – a moment when Dowd should have just sucked it up like a man, perhaps said ‘yeah, you know, sympathize with Kimmel,’ whatever. 

But kept it zipped. And he couldn’t do it.

He’s taking the martyr routine even further, selling t-shirts for ‘Holocaust victims’ (whut) with his immortal words emblazoned on them.

BREAKING: Matthew Dowd is not profiting off his firing from @MSNBC with a new line of t-shirts containing his odious, now-famous slogan.

Only $32! pic.twitter.com/izI3kxsU0y

— Douglass Mackey (@DougMackeyCase) September 20, 2025

And making sure to pipe up with his most probably now trademarked slogan at every inopportune moment, regardless of the circumstances.

Matthew Dowd learned no lessons. pic.twitter.com/xzbbbS6Qx4

— Bluesky Libs (@BlueskyLibs) September 24, 2025

GIVE IT A REST WITH THE DIMESTORE PHILOSOPHICALS, KHALIL GIBRAN

This pathetic, basement-dwelling, WHAT ABOUT ME wussie little rage monkey has earned himself this week’s coveted, bald, non-binary, likely radioactive Chinese statuette.

I am on the hunt for a new nominee.

Oddly, I don’t think I’ll have any trouble.

How sad is that?

Pathetic.

THE NEW YORK POST: Keith Olbermann needs ‘serious help’ as ex-colleagues warn threat-issuing broadcaster is ‘losing it’ – https://t.co/kW4sv3bVDZ

— MIKE LEACH (@michaelaleach) September 25, 2025

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