I have warned many times about the guaranteed dangers of betting with your heart instead of your head - big darkness, soon come - but every once in a while you get a fair chance to have it both ways, and the annual NCAA basketball Tournament is one of them.

The quote by Hunter S. Thompson highlights the tension between emotion and rationality in decision-making, particularly when it comes to betting. Thompson warns about the dangers of betting with your heart—making decisions based on emotion or personal bias—rather than with your head, which represents logic and analysis. He suggests that when you bet emotionally, you're likely to face negative consequences ("big darkness, soon come"). However, he acknowledges that occasionally, there are rare opportunities where one can have both the emotional and rational sides aligned, like during the annual NCAA basketball Tournament.

Thompson’s statement reflects the excitement and unpredictability of the NCAA Tournament, a time when many people, even those who aren't usually inclined to bet, take part in bracket challenges and make predictions about the outcomes. His reference to the tournament is an acknowledgment of the fact that, during this event, the combination of upsets, underdog victories, and unexpected outcomes creates a unique situation where both logic and emotion can guide successful bets. In other words, the tournament presents a rare occasion when following one's heart might not lead to disaster.

The origin of this quote lies in Hunter S. Thompson’s style of writing, which often involved sharp, irreverent commentary on various aspects of American life, including sports. As a journalist and writer, Thompson was known for his unique perspective on popular culture and often took an unconventional approach to issues like gambling and sports fandom. This quote exemplifies his blend of humor, cynicism, and insight into the contradictions of human behavior.

In essence, Thompson’s quote underscores the inherent risks of relying on emotion in decision-making, particularly in the high-stakes world of betting, while also celebrating the rare occasions where intuition and logic can come together to create an exciting and rewarding experience. His words serve as both a cautionary tale and a playful nod to the unpredictability and thrill of events like the NCAA Tournament, where the line between reason and emotion can blur in fascinating ways.