Flint Dille
7 min readMay 10, 2020

FLINT DILLE’S GAME THEORY: The Long Game.

This is going to be about political strategy in 2020, but we’ll start with an old Avalon Hill game called Stalingrad. In this game, the Russians had little chance of wiping out the Germans, but they could stop the Germans from meeting their victory conditions by cleverly using the Russian winter. Winning by not losing. And given that victory is a murky question in real history, it is also one in politics. The Democratic Establishment has won twice in a row over the ‘Progressive’ wing of the party, but the end result probably wasn’t a winning candidate. So, what’s the point?

Point is, not all games are winnable. Sometimes you have to drive the hardest bargain with reality that you can and go for a draw or maybe even a ‘Marginal Victory’ (or Marginal Defeat) leading to victory in the long game. If you are living in a deep blue district and you are red, there is near zero chance that a red candidate is going to win.

You might love your red candidate, but there’s little point in voting for him in a primary, or voting Red for that matter. If you have an open primary state, you’re better off voting for the least offensive Blue option, that is, you may not have the power to tip the election, but you can end up with a better result on election day.

I know many will find this distasteful, but this column about game theory, it’s not about ideological purity.

As a pure game theory proposition, you’re better off tipping the election slightly your way than voting for somebody who is a certain loser in your district.

And let’s look at what else has changed. Not only do you not have a the candidate you didn’t want (notice the double negatives), but your ‘lesser of two evils’ (LOTE) candidate realizes that you are part of their narrow margin for being in office. They will want to keep that margin because they want to stay in office. That means LOTE has to keep you. Margins are the tail that can wag the dog.

If this doesn’t sound real to you, just think about the concept of what right-leaning Republicans call RINO’s (Republican in Name Only). RINOs are disparaged by their own party because they literally don’t go with the Party Line. Why not? Because they come from purple states and rely on ‘crossover’ voters who they fear will discard them if they go too far right.

Democrats have the same issue at this exact moment. Control of the House of Representatives rests on a small percentage of seats in ‘swing’ districts. Whichever party wins enough ‘swing’ districts controls the house. The problem is that every seat that has ‘flipped’ is a district that voted the other way last time and can vote the other way next time. Therefore, the representative from that district usually has to remain ‘moderate’ to keep their seat long enough to gain the real value of incumbency.

If you don’t believe this, ask yourself why parties have ‘whips’. The definition of a ‘whip’ is “the official of a political party whose job is to ensure party cohesion in a legislature. This means ensuring that members of the party vote along party lines, rather than according to their own personal ideology or the will of their constituents.” In other words, the ‘whip’ pressures or bribes a wavering member of their party to follow the party even at the risk of their own political future. It’s also the Whip’s job to count votes and let some members vote the other way in order to preserve their own seat.

Sometimes a whip whips too hard and bad things happen. Whipped too hard over ‘impeachment’, Jeff Van Drew, a Blue Dog Democrat from a ‘swing’ district in Southern New Jersey changed parties, giving Donald Trump bragging rights. And there’s a future problem. Now, the party has to either cede the seat or spend resources trying to get rid of what used to be their own guy. If the turncoat isn’t punished, future whips will have less power.

But back, to Game Theory in districts that are a lock for one of the two parties. Even if your ‘compromise’ candidate loses, future challengers will know that there is a pocket of votes that are up for grabs and will factor this in in upcoming primaries. That is playing the ‘long game’ or ‘looking a few moves down the game.’

Game Theory advice. Play the long game. It might feel good to be a noble loser, but at some point, the noble falls off and you’re just a loser.

Now lets switch sides and apply the long game theory to Progressives (Bernie, et.al followers in the 2020 election). Donald Trump might have a point. Imagine that Elizabeth Warren had dropped out and thrown her support to Bernie Sanders. A couple of states that went Biden might have gone Bernie and he might have been in the race. It might have led to a brokered convention, but Bernie might have won that. Any outcome would have been better for Progressives than a sorry slink off after a Wisconsin Primary.

So Trump saying that had Warren gone ‘Progressive’, the outcome might have been better for Bernie. It couldn’t have been worse. And blame Elizabeth Warren all you want, the real bad gamers are the people who voted for her. It might have given her voters a warm and fuzzy at the time, but it crippled the Progressive movement for 2020.

So, applying game theory, not emotion, what do you do if you’re a Progressive in 2020?

Barring a shocking and unforeseen turn of events, there isn’t going to be a Progressive in the White House inaugurated in January of 2021. A win for Trump is status quo, a Win for Biden is a win for the Democratic Establishment. There’s no other way to look at it. You do not get more establishment than Joe Biden, no matter how much he tries to change the past.

If the Establishment wins in 2020, they go into 2022 and 2024 in a commanding position. The only caveat here is that if Biden selects a progressive V.P., in which case they would be the likely heir-apparent if Biden wanders off. However, that’s dangerous politics and jeopardizes his chances in the general. The real hope for the Progressives is a 2024 ‘Change’ candidate after 8 years of Trump/Pence.

So yeah. As pure Game Theory, Progressives should vote for Trump in 2020 to kill off the Establishment wing of the party.

And here’s where we head back to the lessons of Avalon Hill’s ‘Stalingrad.’ The whole Russian strategy is to buy time, because time was on their side. As happened to Napoleon, Russia’s greatest military asset is their vast terrain and brutal weather. Hence they developed ‘scorched earth’ strategy, sacrificing their own farms to burdon the Nazi supply lines. It takes a lot less food to wait in place than it does to invade. Russia won at a terrible cost, but from a strategic position, their crops and population would would come back, the Germans wouldn’t.

From the ‘Progressive’ point of view, time is their ally. They are young and the ‘establishment’ is old.

At first glance, time seems to be on the Progressive side. But the clock is ticking. We will not emerge from COVID-19 the same culture we were. Just like in Stalingrad, seasons matter. The Spring of Quarantine will turn into Summer, both metaphorically and in reality. Why do progressive forces want the social distancing to go on forever?

Will news media be New York centric when the virus clears? Will New York still be The Big Apple? Will San Francisco progressives continue to dominate California politics? Pelosi and Finstein aren’t the young fresh faces they were in ‘the year of the woman.’ Can the Bay Area hold on to tech forever? Will Tech matter as much when people can touch each other again. Will Google and Apple be cultural forces in a decade? Will an Illinois governor repressing religious gatherings face blowback? Will it fuel a revival?

Millennials are aging. Zoomers are rising. Is a moment passing? Don’t know, but it gut instinct feels like 2024 is do or die for coastal progressives. 2020 is too soon, given the Bernie Sanders implosion. 2028 may be too late.

Game Theoryu suggests that if they sacrifice 2020 to a probable winning incumbent the establishment will have faced two straight losses, the party isn’t likely to go ‘Establishment’ again and will default to a Progressive and, in 2024 the country might have moved far enough that it will elect a Progressive.

You don’t need to look far for examples of this. After McCain and Romney splattered, the Republicans went for an insurgent and a few short years later, the Republican Party looks nothing like it did in 2012. Witness Mitt Romney. He was the party’s candidate in in 2012, now he’s a vanquished outlier in his own party.

So yeah. For the exact same reason that the ‘Red Voter in a Blue District should vote for the lesser of the Blue Evils than the Red Loser, it is a better bet for Progressives to swallow the pill in 2020 to clear the path to the future.

When you can’t win, drive the hardest bargain you can for reality. Lose as gracefully as you can. Use time and terrain to your advantage. There’

When the short game is doomed, it’s best to play the Long Game.