Doug Emhoff: Second Gentleman, White House Gumshoe

Olly Blackburn
The Washington Boast
5 min readJul 21, 2023
The White House

It was one of those DC nights when the air’s so thick you can pour it on a waffle with a side of cream. Even the reptiles were dripping sweat, but enough with the Federalist Society.

Kamala’s on the road at a Rural Broadband junket in San Antonio, I’m in the Observatory kitchen nook nursing a Pamplemousse LaCroix — straight, slice — licking my wounds from the classified documents rumpus. Tell the FBI you found the 2012 inaugural ball seating plan under the president’s barcalounger, next thing you get Dead-Eye Jack Smith busting your chops and the First Lady ghosting you on the real housewives of the West Wing WhatsApp group.

There’s a local anchor on TV saying the White House marching powder case has just been closed, no perp: they found bupkes. I smell a rat. I may have spent the last two years hosting the Whitehouse creche and emceeing Middle School Science Fair luncheons, but this legal dog still has a few tricks — never write off the Hoff!

First stop: the second born, the burnout. Guy whose hard drive leaks strippers and cocaine so hard it has its own pole-dancing permit. I pop Hunter’s door, come in strong, catch the punk off guard in the middle of an om shanti with the circadian rhythms going. “What the fuck’re you doing, Doug!?” kid yells as I tear his duplex apart. That’s when I hear a voice from his Zoom window, “This is highly inappropriate in the middle of a healing session.” I leave the kid to his guru in Sedona, swiping a matchbook from his kimono on the way out.

Matchbook’s from the Senate Dining Club, number scribbled in the corner in red lipstick. Could be a Sharpie. Maybe, biro? I’m pretty sure it’s lipstick. Breathy voice at the end of the line. “Meet me in the Peninsular in 30.” I roll into a cheap room packed with sharks, floozies, two-bit hustlers and delegates from the Ethanol Buyback Recovery conference (meeting on mezzanine level) to find a dame in a Nordstrom pantsuit and a stare that could split glaciers:

“Yellen! What are you doing here?”

“I’m advising the second son on ethical economic policy initiatives.”

From the corner of my eye a sketchy dude eyeing me from the taco station, I chase him out the exit door and across the plaza, into the Capitol right to the Raeburn room…where it’s the Congressional Freedom Caucus bingo night.

It was Gaetz eyeballing me like an Orca scoping a superyacht! He’s with the whole crew. Boebert! Greene! Biggs! Gosar! Maxine Waters..? What’s she doing here? Oh, she wants to borrow their Nespresso machine. I take Gaetz aside, Boebert follows. Gaetz is whining about how measly his congressional salary is, how he has to take his staffers to hotel conventions with free all-you-can-eat taco, pizza and build-your-own-salad stations when Greene tells him to stop being a bitch and eat paleo with the big boys. Boebert hits back, Gosar gets stuck in. A brawl breaks out. Greene has Boebert in a necklock with one arm, Biggs in the other, and Gosar clamped between her thighs squeezing his head like a neo-Nazi walnut while Gaetz cowers in the corner using a staffer’s toddler as a human shield. I split. I’ve a hunch Waters’ presence is no coincidence, but just as I’m about to collar her two lunks pop my nut like a carnival hammer.

Now I find myself in Jack Smith’s corner office. Dead-Eye stares at me squeezing a stress ball with a concertina-ed titanium shell and microbead fill. His flunky, who looks like he just swallowed a wasp and shat a lemon simultaneously, does the talking:

“Back off Hoff, this case is too hot. You don’t want to go where it’s taking you. Trust me.”

Well, that was the subtext. He’s actually rabbiting on about me having too much time on my hands, maybe I want to support my wife on her travels a bit more, Special Counsel Smith is quite capable of handling things himself and will ask for my help if he needs it, yada yada. It’s all blarney, I’m getting too close. I can smell the truth like the backstage odor in the fifth round of a sumo final. Smith, silent as a mortuary slab, doesn’t take his eyes off me. Even when he transfers the stress ball from his left hand to his right then in-between his chin and neck in a kind of nodding duck motion, except the duck has a titanium ball under his chin. Which is disconcerting.

The flunky releases me. Now I’m walking across the Capitol green, crunching leads: Hunter, Yellen, Gaetz, Waters, Smith, all-you-can-eat taco stations….? I’m missing something. Something big. Been there from the start.

The match book!

Midnight in the Senate. I enter a shotgun office on the second floor where the queasy neon shines like month-old velveeta. A wizened old man, face dessicated by decades of rage and corruption looks up at me.

“Grassley!”

Chuck Grassley, senior senator from Iowa. 90-year-old prince of timeless evil.

“You’re the speed-hopper who left an eightball in the West Wing: we both know it!”

“I’m not sure if the senator knows what an eightball is”. So, okay, his small agriculture business adviser was there too.

“Don’t yam me, pencilneck. I know the skinny. State of the Union dinner ’21, you ask Kamala where they sell crack in downtown DC, we figured it was just another racist micro-aggression from a geriatric burnout, but I know you’re a hop-head now. Look at you: 90, jumping steeples. There’s only one way you ain’t no Feinstein: you’re king-pinning a coke racket that funnels product straight from the streets to halls of Congress. Smart. Tight. No one realized. Till now.”

Silence.

“Perhaps the Senator was being kind of mildly racist back there. He was born in a different time, you know.” Grassley’s comms guy. He’s in the room too.

“I wish the 50s never ended, is that racist? Will someone fix me a root beer float.” That’s Grassley.

“Either way, Senator Grassley does not deal in flake cocaine.” Comms guy.

“Just cos he looks like Elmer Fudd in wire-rims and sits on the Judiciary Committee you think you can flim-flam me? I’m the Second Gentleman! I chaired law firms! I teach part-time at Georgetown, motherfucker!” I leap from my seat, grab Grassley, and start popping that freeze-dried Iowan russet off the cowhide walls till he tells the truth.

Which is when the tazer struck my glutes.

A week later now. Here I am, in the Green Room of an Oklahoma Fox Affiliate while Kamala’s interviewed about reproductive rights in native American communities. They said it’s best I don’t stay in DC unattended. I say powerful people are darn scared. The truth is out there. A headline on my Twitter feed: half a trillion’s missing from the upcoming budget negotiations. “Missing..?”

Sounds like a fresh case for Doug Emhoff, Second Gentleman, White House gumshoe. Guardian angel in the town where the deep state swims breast stroke and corruption never sleeps.

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