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History’s Worst Decisions and Daily Fantasy Sports

“Those who cannot remember the past are condemned to repeat it.”
— George Santayana

While most people have no idea who he is — some Texans might confuse him with the guy who laid siege to the Alamo — Santayana is one the most quotable writers of the last 200 years. As far as philosophical one-liners go, the essayist and novelist from Madrid is probably surpassed by only Mark Twain and Oscar Wilde — and there’s no shame in that. Everyone is surpassed by Twain and Wilde.

Santayana spit words the way Chris Paul drops dimes. Here are some quotations for which he’s responsible:

  • “Beauty as we feel it is something indescribable: what it is or what it means can never be said.”
  • “Happiness is the only sanction of life: where happiness fails, existence remains a mad and lamentable experiment.”
  • “The highest form of vanity is love and fame.”
  • “To call war the soil of courage and virtue is like calling debauchery the soil of love.”
  • “It is not society’s fault that most men seem to miss their vocation. Most men have no vocation.”
  • “Fashion is something barbarous, for it produces innovation without reason and imitation without benefit.”
  • “Art like life should be free, since both are experimental.”
  • “Eternal vigilance is the price of knowledge.”
  • “There is no cure for birth and death save to enjoy the interval.”
  • “Skepticism is the chastity of the intellect.”
  • “Only the dead have seen the end of war.”

That last one is famously misattributed to Plato, but it belongs to Santayana. That he once wrote a sentence good enough to make people think it was Plato’s is an accomplishment.

Anyway, this piece isn’t about Santayana. It’s about remembering the past so as not to repeat it — sort of.

History’s Worst Decisions

One of my New Year’s resolutions was to read more, and I’m slaying books the way that Drew Brees dominates the Superdome. After finishing The Little Book of Answers (mentioned in my piece on the gambler’s fallacy), I’ve turned my attention to a delightful (nay, delicious) read called History’s Worst Decisions by Stephen Weir. The book’s about . . . history’s worst decisions . . . and the people who made them.

Recently I published a Labyrinthian about how to be a positive expected value FantasyLabs subscriber. With that EV perspective in mind, you might wonder how Weir decided which decisions to include and the criteria he used to sort through the decisions?

  • Are these decisions ‘bad’ only because their outcomes are bad?
  • Does Weir take into account the odds of the various outcomes associated with the decisions?
  • Could the negative consequences of these decisions actually be anticipated at the time and by the decision-makers?

Here’s (an excerpt of) what Weir has to say in his introduction:

This book takes a journey through the sheer idiocy of humanity. These are not honest blunders but really, really dumb ones; not just poor choices but choices with very nasty implications for the rest of us. Inclusion in History’s Worst Decisions and the People Who Made Them demands idiocy that exacted a very high price, in lives or livelihoods, or sometimes even the end of countries and dynasties.

A book such as this needs operating principles. It’s too easy to blame sheer stupidity. No one that dumb really gets much chance to make dumb decisions that truly matter (royal families and heirs or heiresses excluded). Many are impelled by emotions outside their control to lose whatever sense they may once have had, and Pope Gregory the Great, in the late sixth century, kindly categorized these types of emotions as the Seven Deadly Sins. But it would be foolish to believe that only the wicked are stupid. So you will also find examples of each of the Cardinal Virtues, impelling their followers to utmost folly.

Naturally, after I first read that passage I had some thoughts about daily fantasy sports.

Often, Negativity is a Virtue

I’m not a fan of the phrase “constructive criticism.” Regardless of how criticism is intended, it can always be constructive if the person receiving the criticism has the right mindset. Criticism doesn’t need to be destructive. For people always seeking to improve, almost anything can constitute advice, which is what criticism is or at least should be.

This is especially true for (non-clinical) self-criticism. People who fashion themselves into better DFS players, better entrepreneurs, better athletes, etc., tend to understand that form follows failure. They don’t ignore their strengths, but they often focus on their weaknesses and dedicate time and energy (and sometimes money) to erasing that deficiency.

Just as scientific advancement is often based on the negative perspective of strong inference, personal attainment is often rooted in the strength to acknowledge one’s weaknesses and then will oneself to overcome them. In this regard, negativity can be a virtue.

As DFS players, we increase the odds that we won’t repeat our stupid mistakes if we review our lineups with a critical perspective. Specifically, we should spend the majority of our lineup review time studying losing lineups. It’s nice to review winning lineups, but (arguably) the best part of the reviews by Labs Co-Founder Peter Jennings (CSURAM88) is hearing what he has to say about his lineups that suck.

Sometimes, he’ll study a lineup and say, “I didn’t get the result I wanted, but the process was still good, so I feel good about the lineup.” Other times he’ll say, “I was a total donkey, I didn’t really think this through, and that’s something I need to keep in mind and work on in the future.” Listening to Peter talk about ways in which he fails and can improve is a +EV use of time. (By the way, CSURAM88’s lineup reviews are accessible via our Premium Content Portal. While those and our podcasts are available to anyone, the rest of the content on the portal is reserved for Pro subscribers.)

The person who plays DFS but doesn’t review performance with a negative perspective probably won’t play DFS successfully or for long. To clarify: By “performance,” I don’t mean “how much money was won or lost in a slate.” I’m not talking about results. I’m talking about process — the way decisions are made and enacted — regardless of outcome.

It’s not enough to look at the account balance on DraftKings or FanDuel and say, “I made money on that slate so it’s all good.” It’s possible to make money in isolated slates through -EV tactics. Ultimately, though, people lose money if they don’t routinely look for mistakes to correct.

In the Extreme, a Virtue Can Be a Sin

I appreciate Weir’s point that Cardinal Virtues (just like Deadly Sins) can lead to horrible decisions. There are many ways to do something right — and usually even more ways to do it wrong.

DFS success is not the result of any particular style, but CSURAM88 is so good in part because he’s learned how to leverage his individual perspective and abilities. CSURAM88 is chalkier than a 1950s college chemistry professor — but that works for him. In much the same way, Labs Co-Founder Jonathan Bales is a cobra of contrarianism — but that works for him. Successful players learn how to succeed with their different skill sets.

At the same time, it’s possible that what is ordinarily a DFS virtue for a given player can lead to horrible decisions. In any contest it’s possible for CSURAM88 to be too chalky and for Bales to be too contrarian. As George Weasley reminds us, sometimes feeling saintlike means being holey.

By the way, writing that last sentence was a bad decision: It’s possible to have too many Harry Potter references.

Another Bad Decision

It’s also possible to have too much corniness. I’d know. I live in Iowa.

The Labyrinthian: 2017.25, 120

This is the 120th 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. Previous installments of The Labyrinthian can be accessed via my author page.

“Those who cannot remember the past are condemned to repeat it.”
— George Santayana

While most people have no idea who he is — some Texans might confuse him with the guy who laid siege to the Alamo — Santayana is one the most quotable writers of the last 200 years. As far as philosophical one-liners go, the essayist and novelist from Madrid is probably surpassed by only Mark Twain and Oscar Wilde — and there’s no shame in that. Everyone is surpassed by Twain and Wilde.

Santayana spit words the way Chris Paul drops dimes. Here are some quotations for which he’s responsible:

  • “Beauty as we feel it is something indescribable: what it is or what it means can never be said.”
  • “Happiness is the only sanction of life: where happiness fails, existence remains a mad and lamentable experiment.”
  • “The highest form of vanity is love and fame.”
  • “To call war the soil of courage and virtue is like calling debauchery the soil of love.”
  • “It is not society’s fault that most men seem to miss their vocation. Most men have no vocation.”
  • “Fashion is something barbarous, for it produces innovation without reason and imitation without benefit.”
  • “Art like life should be free, since both are experimental.”
  • “Eternal vigilance is the price of knowledge.”
  • “There is no cure for birth and death save to enjoy the interval.”
  • “Skepticism is the chastity of the intellect.”
  • “Only the dead have seen the end of war.”

That last one is famously misattributed to Plato, but it belongs to Santayana. That he once wrote a sentence good enough to make people think it was Plato’s is an accomplishment.

Anyway, this piece isn’t about Santayana. It’s about remembering the past so as not to repeat it — sort of.

History’s Worst Decisions

One of my New Year’s resolutions was to read more, and I’m slaying books the way that Drew Brees dominates the Superdome. After finishing The Little Book of Answers (mentioned in my piece on the gambler’s fallacy), I’ve turned my attention to a delightful (nay, delicious) read called History’s Worst Decisions by Stephen Weir. The book’s about . . . history’s worst decisions . . . and the people who made them.

Recently I published a Labyrinthian about how to be a positive expected value FantasyLabs subscriber. With that EV perspective in mind, you might wonder how Weir decided which decisions to include and the criteria he used to sort through the decisions?

  • Are these decisions ‘bad’ only because their outcomes are bad?
  • Does Weir take into account the odds of the various outcomes associated with the decisions?
  • Could the negative consequences of these decisions actually be anticipated at the time and by the decision-makers?

Here’s (an excerpt of) what Weir has to say in his introduction:

This book takes a journey through the sheer idiocy of humanity. These are not honest blunders but really, really dumb ones; not just poor choices but choices with very nasty implications for the rest of us. Inclusion in History’s Worst Decisions and the People Who Made Them demands idiocy that exacted a very high price, in lives or livelihoods, or sometimes even the end of countries and dynasties.

A book such as this needs operating principles. It’s too easy to blame sheer stupidity. No one that dumb really gets much chance to make dumb decisions that truly matter (royal families and heirs or heiresses excluded). Many are impelled by emotions outside their control to lose whatever sense they may once have had, and Pope Gregory the Great, in the late sixth century, kindly categorized these types of emotions as the Seven Deadly Sins. But it would be foolish to believe that only the wicked are stupid. So you will also find examples of each of the Cardinal Virtues, impelling their followers to utmost folly.

Naturally, after I first read that passage I had some thoughts about daily fantasy sports.

Often, Negativity is a Virtue

I’m not a fan of the phrase “constructive criticism.” Regardless of how criticism is intended, it can always be constructive if the person receiving the criticism has the right mindset. Criticism doesn’t need to be destructive. For people always seeking to improve, almost anything can constitute advice, which is what criticism is or at least should be.

This is especially true for (non-clinical) self-criticism. People who fashion themselves into better DFS players, better entrepreneurs, better athletes, etc., tend to understand that form follows failure. They don’t ignore their strengths, but they often focus on their weaknesses and dedicate time and energy (and sometimes money) to erasing that deficiency.

Just as scientific advancement is often based on the negative perspective of strong inference, personal attainment is often rooted in the strength to acknowledge one’s weaknesses and then will oneself to overcome them. In this regard, negativity can be a virtue.

As DFS players, we increase the odds that we won’t repeat our stupid mistakes if we review our lineups with a critical perspective. Specifically, we should spend the majority of our lineup review time studying losing lineups. It’s nice to review winning lineups, but (arguably) the best part of the reviews by Labs Co-Founder Peter Jennings (CSURAM88) is hearing what he has to say about his lineups that suck.

Sometimes, he’ll study a lineup and say, “I didn’t get the result I wanted, but the process was still good, so I feel good about the lineup.” Other times he’ll say, “I was a total donkey, I didn’t really think this through, and that’s something I need to keep in mind and work on in the future.” Listening to Peter talk about ways in which he fails and can improve is a +EV use of time. (By the way, CSURAM88’s lineup reviews are accessible via our Premium Content Portal. While those and our podcasts are available to anyone, the rest of the content on the portal is reserved for Pro subscribers.)

The person who plays DFS but doesn’t review performance with a negative perspective probably won’t play DFS successfully or for long. To clarify: By “performance,” I don’t mean “how much money was won or lost in a slate.” I’m not talking about results. I’m talking about process — the way decisions are made and enacted — regardless of outcome.

It’s not enough to look at the account balance on DraftKings or FanDuel and say, “I made money on that slate so it’s all good.” It’s possible to make money in isolated slates through -EV tactics. Ultimately, though, people lose money if they don’t routinely look for mistakes to correct.

In the Extreme, a Virtue Can Be a Sin

I appreciate Weir’s point that Cardinal Virtues (just like Deadly Sins) can lead to horrible decisions. There are many ways to do something right — and usually even more ways to do it wrong.

DFS success is not the result of any particular style, but CSURAM88 is so good in part because he’s learned how to leverage his individual perspective and abilities. CSURAM88 is chalkier than a 1950s college chemistry professor — but that works for him. In much the same way, Labs Co-Founder Jonathan Bales is a cobra of contrarianism — but that works for him. Successful players learn how to succeed with their different skill sets.

At the same time, it’s possible that what is ordinarily a DFS virtue for a given player can lead to horrible decisions. In any contest it’s possible for CSURAM88 to be too chalky and for Bales to be too contrarian. As George Weasley reminds us, sometimes feeling saintlike means being holey.

By the way, writing that last sentence was a bad decision: It’s possible to have too many Harry Potter references.

Another Bad Decision

It’s also possible to have too much corniness. I’d know. I live in Iowa.

The Labyrinthian: 2017.25, 120

This is the 120th 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. Previous installments of The Labyrinthian can be accessed via my author page.

About the Author

Matthew Freedman is the Editor-in-Chief of FantasyLabs. The only edge he has in anything is his knowledge of '90s music.