
Kentucky politics occupies a unique place on the national stage, with Thomas Massie, Rand Paul, and Andy Beshear having varying degrees of fame for bucking trends and norms. We wrote about Rand Paul as a potential longshot Republican nominee for President and Beshear as a possible Democratic darkhorse already, in our short (but storied) existence.
Here we find ourselves again.
On Tuesday, Kentucky Republicans will get to pick their nominee for the 4th Congressional District between the incumbent, Massie, and his challenger, Ed Gallrein. It is, by almost all accounts, completely unprecedented. The record money spent, President Trump’s push against Massie — even Pete Hegseth campaigned for Gallrein on Monday, which the New York Times called “an extraordinary breach of military decorum.”
Last week, Bill Cassidy lost his primary in Louisiana; Trump claimed victory (he had full-throatedly endorsed Cassidy’s main opponent, Julia Letlow). And after the results were announced, the KY-04 primary markets immediately flipped. Gallrein is the green line in the image below, Massie is the blue. They criss-cross on May 16th at about 10 p.m.:

The same thing happened on Polymarket:

And for as much sense as this makes on the surface, we may be seeing too much of a knee-jerk reaction.
The market is starting to correct itself a little, as Massie went back up slightly, from 39% to 42% between 6:30 pm ET and 8:30 pm ET Monday night. As of right now, Massie is up to 44%. But still — should it have swung that wildly? Or even at all? Cassidy and Massie aren’t even in the same universe, really. Sure, Trump pushed against both of them and they’re Republicans, but that’s where it ends.
Cassidy’s primary, for instance, was for a Senate seat and open to the entire state; Massie represents a much smaller district. And Cassidy had a little bit of the opposite problem as Massie — he flip-flopped his Trump sycophancy, voting to impeach him and later catching flak for confirming RFK Jr. (among other things). Cassidy was accused by his constituents of revisionist pandering; the full state of Louisiana — capturing a wide swath of Republicans — had a chance to bury him, and they did.

And really, this “Cassidy Lost!” storyline is insulting to Letlow, who is charismatic, camera-ready, has a fantastic backstory, won her first (tragedy-marred) election in a landslide, and was already a state rep with legislative chops. Cassidy finished third. He could have just been an unlikable politician, and Letlow a much better candidate for senator, period — Trump or no Trump.

Massie, meanwhile, has been pretty open in his convictions, and has reliably stuck to them, repeating the mantra that he’s representing his district. People in Massie’s district seem to actually like and trust him. This is not an unpopular senator; this is a relatable local-centric representative (he invented a roving chicken coop, for instance) who connects with his constituents. And while the numbers are trending in the wrong direction for Massie on the markets, my question for buying his win in the primary isn’t “should I?” but “when?” The most opportune moment at 39¢ has passed, but I’m still in at 42¢. Massie’s district is full of commuters to Cincinnati living in Kentucky because it’s supposed to be more affordable. High gas prices for the commute are going to have more of an effect than the polls and markets give them credit for. And that’s just the tip of the iceberg.
Yes, the recent spate of Trump-backed wins in Indiana and Louisiana is a little worrisome for the Massie cause, but this particular case in this particular area with this particular politician is unique enough for a confident buy on Massie.
A Second Massive Massie Market Makes Things Interesting
Just to throw another curveball, there’s currently a $1 million-plus market on the expected margin of victory for Massie/Gallrein — and Massie at 0-5% is in the lead:

My hunch is this is Gallrein believers splitting the vote between the 0-5% and 5-10% range. But here’s the thing… if I start with “Massie is going to win,” I can choose between three likely outcomes:
31¢ on a 0-5% win for Massie
10¢ on a 5-10% win for Massie
42¢ to cover any Massie scenario in the original market
$20 on an outright Massie win gets me $48. But I can put $10 on 0-5% and it gets me $33, while another $10 on 5-10% gets me $109. Is it worth splitting up my $20 for a shot at $109 (with a downside of $33)? Massie’s district isn’t full of backwoods Kentuckians that buyers may be picturing — you can see Cincinnati’s skyline from a lot of his district. There are fancy horse tracks. Distilleries. Massie may be contrarian, but he’s dependably contrarian — and most of his contrarian stances are popular: releasing the Epstein files and getting out of Iran, for instance.
So…all of this leads me to the plays of the day. I’m going for the big swing. And I might be wrong, but there’s no fun is going with a 60% front-runner, right? I know Massie’s area! I’ve been there several times!
We’re splitting our money. $10 on a 0-5% Massie win and $10 on a 5-10% Massie win. if we only get $33? It’s still a W.
