Voting Libertarian… Kinda… In November.

I am voting Libertarian in the November election. The decision was not easy, and it involves more calculated thinking that I would care to admit.  At the same time, watching the Libertarian nominee for president kick off the early stages of her campaign makes me wonder what I have chosen to support. Consequently, I am not sure whether I am voting based on principle or on rebellion.

Let’s start with the decision to vote Libertarian. President Trump has accomplished a lot that I agree with during his term. He also has, at times, engaged in the same decisions for political convenience that made me support him in the 2016 Republican primary. He led the effort to grant one of the biggest welfare handouts in the country’s history in a futile effort to prop up the economy and his poll numbers. His conduct in response to the Russian investigation was less than stellar despite the fact that it appears to be a set-up. In other words, his principles have become flexible just like the Republicans who drove me to support Trump due to their linguine spines.

At the same time, my wallet won’t allow me to support Joe Biden’s 2.0 version of Barack Obama’s presidency. I also cannot tolerate the rabid attack on my identity that is disguised as a pseudo-moral appeal to engage in a battle between “good” and “evil.”

Consequently, my options were holding my nose and voting for President Trump, not voting at all, or voting for a third party candidate. I have not missed an election in my life so the second option was not all that appealing. I chose third party.

I intended to vote Libertarian long before Justin Amash brought ultra-conservatives with him when he joined the Libertarian Party. My rationale was more defensive than it was principled. Under the current electoral college system, my vote does not matter in Connecticut if I vote for Trump. Because I am fed up with the two national parties, a Libertarian vote represents an act of rebellion – a statement against entrenched and complacent political parties whose principles shift like water.

Wake up and get a spine.

That brings me to why my Libertarian vote is a kinda vote. I know Libertarians that range from the very intelligent and grounded (i.e., friends at the Cato Institute) to the looney and off-the-wall. The political tent is big enough for all of them. It’s just a very disorganized and intellectually frustrating tent at times.

I have been acquainted with the party and its doings since I was 16. It relies heavily on grassroots support to assemble a political base, which often means that the people with the biggest bullhorn control its message. The results have not been jaw-dropping. It also breeds a certain political complacency, which leads to repeats of history and failure. Einstein would call it insanity.

Political realities like funding and realistic expectations dictate strategy, and a cautious strategy undoubtedly weighs in favor of tried and true methods to deliver respectable performances. Respectable performances are not necessarily winning performances though, and cautious strategies are almost always reactionary. Politics, unfortunately, kill the reactionary and reward the proactive.

Since college, I have been a student and a fan of Colonel John Boyd’s OODA loop theory. Originally intended to provide a methodological decision-making framework in dogfights, many fields have adapted it to strategic decision-making (I was exposed to it in business school as a secondary reading, and I have used it in my legal career). A rudimentary principle of Boyd’s theory is to control the operative conditions to shorten your opponent’s time to make a decision or to make your opponent’s decision overly complex. In other words, being proactive and unpredictable wins.

Libertarians are frustrating because they don’t play the political game proactively as a party. Facing a deeply divided country that dislikes both Trump and Biden, they have yet to take the unpredictable and proactive risks that will place them in the national eye and force Biden and Trump to confront them as a true political threat.

It’s a shame because they have a lot to offer a deeply dissatisfied country right now. They just don’t know how to offer it, and it doesn’t look like they will any time soon.

Consequently, I will be voting for the Libertarian nominee for president, Jo Jorgensen, but I won’t be voting in confidence for her political skills or the political skills of the Libertarian Party.

P.S. I am happy and egotistical enough to offer the Libertarians my strategic advice.