"The race is often to the swift, and the battle to the strong, but the way to bet is on those with miscalibrated odds."
If the odds are well calibrated, the expected return is zero; we might as well not bet. The same goes for speculating on well-priced assets.
If we have reason to believe that the odds/prices are miscalibrated, we can expect a positive return by going long/short (depending on which direction they're off).
Interacting with a bookie is a whole different context than interacting with reality.
I think the point of the article was that interacting with the stock market (and potentially other areas of many businesses) is more like interacting with a bookie than interacting with reality.
I can think of a few reasons not to follow this strategy:
- If our uncertainty is too high, we might want to avoid the risk; e.g. even if Georgia wins, we might not get anything out of it.
- If the commitment is too high, e.g. a Martingale.
- If setting up one outcome puts another at risk; e.g. if we fund Georgia's war effort, such that Russia would retaliate if they win; or the other way around; or both!
"Again I saw that under the sun the race is not to the swift, nor the battle to the strong, nor bread to the wise, nor riches to the intelligent, nor favor to those with knowledge, but time and chance happen to them all." —Ecclesiastes 9:11
To understand where Ecclesiastes is coming from:
In the wisdom literature, books like Proverbs will typically state the common case and it's Ecclesiastes that will state the exception. This keeps the wisdom literature balanced as a set of principles, not rules.
The Hugh Keough quote is a great summary then of the main point, which I won't restate.
> you want to bet on the mispriced horse, not the horse most likely to win