This is the 146th installment of The Labyrinthian, a series dedicated to exploring random fields of knowledge in order to give you unordinary theoretical, philosophical, strategic, and/or often rambling guidance on daily fantasy sports. Consult the introductory piece to the series for further explanation.

I’ve written before about the role of luck and the role of reading in DFS success. Now, I’m randomly going to talk about luck based on some stuff I just read.

You’re welcome.

Two Books

One of my New Year’s resolutions was to read more. True to form, this year I’ve done a remarkable job of starting books. I’ve finished few of them — but almost no one in the world starts books with my flourish. Like Steve Trevor, I’m “above average.”

My understanding is that if I refer to a book in a piece then I can write it off as a tax expense. Granted, my legal expertise extends only so far — but this sounds right. With that in mind, I’d randomly like to mention two books I’m currently reading (and amazingly might finish):

  • Cave Canem: A Miscellany of Latin Words and Phrases, by Lorna Robinson
  • One Bloody Thing After Another: The World’s Gruesome History, by Jacob F. Field

Given that my brain is probably the only one weird enough to filter through the information in these books and think, “This definitely applies to DFS,” I don’t recommend you read either of these books, but . . .

  1. Some stuff I read in them made me think of DFS.
  2. I can now write these books off as an expense.


Also, I can’t stress this enough: When it comes to the tax code, I’m not a legal expert. Or any kind of expert. About anything.

Julius Caesar and the Rubicon River

The Rubicon is a river in northeastern Italy (according to the two books on my desk and also Wikipedia; mainly Wikipedia). It separates Italy on the south and the province of Gaul on the north. In the Roman Republic, it was treasonous for a commander to cross the Rubicon and enter into Italy proper with his army if he wasn’t specifically permitted to do so by the Senate.

In 50 BCE, Caesar’s second five-year term as the governor of Cisalpine Gaul ended, and he was thus ordered to disband his army and return to Rome by the Senate, which feared that Caesar was gaining too much power. Proving that fear begets fear, Caesar worried that if he returned to Rome without magisterial immunity, he would be captured and tried as a traitor. As a result, Caesar’s former Triumvir and former son-in-law Pompey — the Roman consul — accused Caesar of insubordination, which unsurprisingly encouraged Caesar to act insubordinate.

Not unlike Robb Stark, Caesar decided to travel south to the capital, “but not alone.” On January 10, 49 BCE, Caesar crossed the Rubicon, bringing with him the famed Legio XIII Gemina (the 13th Twin Legion) — not his entire army. With the reduced number of soldiers, Caesar advanced on Rome at an unbelievable pace. According to one historian, Caesar and his men moved so quickly that the messengers who traveled to Rome to warn the Senate of Caesar’s approach barely beat him there. Even though Pompey had more soldiers, he and the Senate fled the capital.

After a series of battles — some of which he nearly lost — Caesar defeated Pompey, who in 48 BCE fled one final time to Egypt, where he was assassinated by Ptolemy XIII’s bodyguards. When Caesar arrived to Egypt and was presented with Pompey’s head and ring, he insisted that Pompey be given a proper Roman burial. Distrusting Ptolemy, Caesar did what most people in his position would’ve done: He took Cleopatra — Ptolemy’s wife, sister, and political rival — as his mistress. Shortly after impregnating Cleopatra and solidifying her position on the throne, Caesar defeated Ptolemy at the Battle of the Nile, soon after which Ptolemy drowned in the river while trying to flee.

Sometimes history can be wonderfully metaphorical.

“The Die Has Been Cast”

When Caesar crossed the Rubicon with his soldiers, he’s reported by Plutarch and other ancient writers to have said “Alea iacta est” (or something similar to that in Latin or maybe even Greek), which translates into English as “The die has been cast.” (Some scholars think, depending on what he actually said, the translation should be “Let the die be cast.” Either way.) Like Freedman quoting a bad ’90s movie — “suck me, beautiful” — Caesar was quoting the Greek comedic playwright Menander.

Here’s what I find intriguing: Caesar is considered a great military commander, maybe one of the best generals in history. Students still read his accounts of the Gallic Wars. He conquered the Germanic tribes, the Britons, and his political enemies — often with fewer soldiers — and even when he lost battles he still somehow seemed to gain strategic edges in defeat, like a chessmaster sacrificing pieces. Caesar was basically the Bill Belichick or Gregg Popovich of classical conflict. He was an Art of War-caliber tactician.

And, yet, at his moment of destiny — the moment that would define the rest of his life — despite all the skill he possessed, he thought of the future not as a process within his control but as a game of luck: “The die has been cast.”

Being comfortable with luck is probably a skill.

Daily Fantasy Caesar

In everything we do — playing poker, investing in various markets, making movies, finding life partners, pulling out of a long, narrow driveway in reverse at night, shooting arrows, etc. — a degree of luck is always involved, no matter how skilled we are. My sense is that many people attempt to deny the role luck plays in life. They don’t wish to think of themselves as existing in a universe (or maybe just a world) where they cannot control their future. This perspective is remarkably fragile and flawed.

The long-term perspective knows that uncertainty is the only certainty. Those who walk the long road know that luck is endemic to being alive. They don’t ignore randomness. Rather, they seeks to leverage it in a skillful way. They look for Black Swans.

It’s not as if I want to say that DFS and gambling are the same, because they aren’t . . . except they are, because everything is similar to gambling — especially to people who appreciate the degree to which luck dominates life.

Embrace the extent to which every (daily fantasy) event is a cast of the die.

Inconclusive Conclusion

Here are some final random thoughts:

  • Caesar didn’t take his entire army with him when he crossed the Rubicon. Sometimes speed and efficiency matter more than size and volume. Also, when you’re making the defining gamble of your life, don’t invest all your resources.
  • When Caesar metaphorically cast the die, his life was at stake. If he didn’t win, he would die. He had the ultimate skin in the game.
  • Lord Grantham from Downton Abbey is the only person in regular conversation I’ve ever heard say, “Cross the Rubicon” — but he’s a character in a TV show and a relatively useless person. If you ever want to say that your daughter who married the chauffeur is now past the point of no return because she’s pregnant, don’t say that she’s crossed the Rubicon. Just say that she’s past the point of no return. Also, be less of a sh*thead.
  • If you want to be someone with an awesome life in ancient Rome, know that at some point you’re probably going to die uncomfortably. Of course, that applies to almost everyone anyway, so what the f*ck do you have to lose? Build that hot tub time machine.

Also, I probably shouldn’t end this piece without mentioning that we have the best suite of DFS Tools ever.

Rubicon crossed.


The Labyrinthian: 2017.51, 146

Previous installments can be accessed via my author page or the series archive.