My latest book, A Hacker’s Mind, has a lot of sports stories. Sports are filled with hacks, as players look for every possible advantage that doesn’t explicitly break the rules. Here’s an example from pickleball, which nicely explains the dilemma between hacking as a subversion and hacking as innovation:

Some might consider these actions cheating, while the acting player would argue that there was no rule that said the action couldn’t be performed. So, how do we address these situations, and close those loopholes? We make new rules that specifically address the loophole action. And the rules book gets longer, and the cycle continues with new loopholes identified, and new rules to prohibit that particular action in the future.

Alternatively, sometimes an action taken as a result of an identified loophole which is not deemed as harmful to the integrity of the game or sportsmanship, becomes part of the game. Ernie Perry found a loophole, and his shot, appropriately named the “Ernie shot,” became part of the game. He realized that by jumping completely over the corner of the NVZ, without breaking any of the NVZ rules, he could volley the ball, making contact closer to the net, usually surprising the opponent, and often winning the rally with an un-returnable shot. He found a loophole, and in this case, it became a very popular and exciting shot to execute and to watch!

I don’t understand pickleball at all, so that explanation doesn’t make a lot of sense to me. (I watched a video explaining the shot; that helped somewhat.) But it looks like an excellent example.

The blog post also links to a 2010 paper that I wish I’d known about when I was writing my book: “Loophole ethics in sports,” by Øyvind Kvalnes and Liv Birgitte Hemmestad:

Abstract: Ethical challenges in sports occur when the practitioners are caught between the will to win and the overall task of staying within the realm of acceptable values and virtues. One way to prepare for these challenges is to formulate comprehensive and specific rules of acceptable conduct. In this paper we will draw attention to one serious problem with such a rule-based approach. It may inadvertently encourage what we will call loophole ethics, an attitude where every action that is not explicitly defined as wrong, will be seen as a viable option. Detailed codes of conduct leave little room for personal judgement, and instead promote a loophole mentality. We argue that loophole ethics can be avoided by operating with only a limited set of general principles, thus leaving more space for personal judgement and wisdom.