This is actually my third attempt (in seven years) at a thread discussing the application of Game Theory to Pokemon battling. Despite good intentions, my first thread was compromised by a very basic understanding of key concepts, and I had trouble articulating my thoughts second time around. I hope that now I can finally offer something coherent, educational, and perhaps even interesting, to the average reader.
The Case for Jolly
During ancient times (the first and second generations), it was accepted that a perfect speed DV (a hexadecimal "deter value" for the uninitiated!) was absolutely necessary for competitive battling. Yet, this need for speed was forgotten during the early days of the third generation, as early innovators took awhile to understand the new IV/EV mechanics. However, everybody would once again fall in love with speed, this time manifesting as the dominance in usage of Jolly and Timid natures over Adamant and Modest.
Fast forward to the sixth generation, and we remain infatuated with speed, and rightly so. To illustrate, consider the following scenario:
1. We have Mega Charizard X, base 100 speed, 299 Adamant, 328 Jolly.
2. Our opponent (villain) has a Lucario (that can Mega Evolve this turn), base 90 speed, 279 Adamant, 306 Jolly.
3. Assume that half of all Mega Charizard X are Adamant, and the other half are Jolly. Assume also that half of all Lucario are Adamant, and the other half are Jolly. According to October statistics, Adamant Charizard X and Jolly Lucario are more common, but this assumption is fine for our purposes.
4. Neither player knows the opposing Pokemon's nature.
5. Assume that villain is competent. Therefore, he knows that switching out risks giving us a free Dragon Dance, potentially costing the battle. He uses a Jolly Lucario.
Exhibit A: The Adamant Pay-Off Matrix
Villain will certainly switch sometimes, and possibly the majority of the time, but he is actually making a significant mistake if that percentage is much higher than 50%, because of our assumption that 50% of Charizard X are Adamant (and therefore slower than Jolly Lucario).
Villain should play a mixed strategy where he sometimes Mega Evolves and uses Close Combat:
252+ Atk Adaptability Mega Lucario Close Combat vs. 0 HP / 4 Def Mega Charizard X: 284-336 (95.62 - 113.13%)
Not only is this a dominant strategy when Charizard is Adamant (meaning that the pay-off is superior regardless of our decision), but we sometimes uses Dragon Dance, and Mega Lucario can KO next turn with Bullet Punch. If Charizard uses Flare Blitz, it faints to recoil anyway.
If we are using Adamant Charizard, and we know that 50% of Lucario are Jolly, and that villain does not always switch, then we must sometimes switch as well, unless we can afford to lose Charizard.
Exhibit B: The Jolly Pay-Off Matrix
The game changes with a Jolly Mega Charizard X. Flare Blitz is now a dominant strategy, and we benefit regardless of villain's decision.
In short, being faster than the opposing Pokemon means that we use fewer mixed strategies, and therefore have fewer opportunities to make mistakes. This is because we are more often in a position where a dominating strategy exists.
The Illusion of Choice
Choice items are the embodiment of risk/reward in competitive battling, but the word "choice" is a misnomer. Sometimes, one (or more) attacks are never an option. The best illustration of this idea is Earthquake. Consider the following scenario:
1. We have a Choice Scarf Garchomp.
2. Our opponent has a Heatran. Villain also has a 100% healthy Dragonite. Stealth Rocks is not in play.
Unless we can deal with +1 Dragonite, Earthquake is never an option in this situation. A good opponent will know this.
Turn Zero
On Pokemon Showdown, the battle begins before the first turn. You can view your opponent's Pokemon, and can therefore tailor your lead to gain an advantage. For example, against a team of physical threats, I lead with Gyarados for an immediate Intimidate. I otherwise never lead with Gyarados.
You should also identify your most valuable Pokemon based on likely favourable match ups. For example, if I see a Gliscor, Gengar is automatically my MVP (unless I have even more compelling options), because I can switch in with impunity, and use Substitute as Gliscor switches out. From turn one onwards, it is a sequential game to engineer this precise match up.
Additional content to come when I'm more inspired and less lazy.
Related: Pokemon Breeding: A Lesson in Economics
The Case for Jolly
During ancient times (the first and second generations), it was accepted that a perfect speed DV (a hexadecimal "deter value" for the uninitiated!) was absolutely necessary for competitive battling. Yet, this need for speed was forgotten during the early days of the third generation, as early innovators took awhile to understand the new IV/EV mechanics. However, everybody would once again fall in love with speed, this time manifesting as the dominance in usage of Jolly and Timid natures over Adamant and Modest.
Fast forward to the sixth generation, and we remain infatuated with speed, and rightly so. To illustrate, consider the following scenario:
1. We have Mega Charizard X, base 100 speed, 299 Adamant, 328 Jolly.
2. Our opponent (villain) has a Lucario (that can Mega Evolve this turn), base 90 speed, 279 Adamant, 306 Jolly.
3. Assume that half of all Mega Charizard X are Adamant, and the other half are Jolly. Assume also that half of all Lucario are Adamant, and the other half are Jolly. According to October statistics, Adamant Charizard X and Jolly Lucario are more common, but this assumption is fine for our purposes.
4. Neither player knows the opposing Pokemon's nature.
5. Assume that villain is competent. Therefore, he knows that switching out risks giving us a free Dragon Dance, potentially costing the battle. He uses a Jolly Lucario.
Exhibit A: The Adamant Pay-Off Matrix

Villain will certainly switch sometimes, and possibly the majority of the time, but he is actually making a significant mistake if that percentage is much higher than 50%, because of our assumption that 50% of Charizard X are Adamant (and therefore slower than Jolly Lucario).
Villain should play a mixed strategy where he sometimes Mega Evolves and uses Close Combat:
252+ Atk Adaptability Mega Lucario Close Combat vs. 0 HP / 4 Def Mega Charizard X: 284-336 (95.62 - 113.13%)
Not only is this a dominant strategy when Charizard is Adamant (meaning that the pay-off is superior regardless of our decision), but we sometimes uses Dragon Dance, and Mega Lucario can KO next turn with Bullet Punch. If Charizard uses Flare Blitz, it faints to recoil anyway.
If we are using Adamant Charizard, and we know that 50% of Lucario are Jolly, and that villain does not always switch, then we must sometimes switch as well, unless we can afford to lose Charizard.
Exhibit B: The Jolly Pay-Off Matrix

The game changes with a Jolly Mega Charizard X. Flare Blitz is now a dominant strategy, and we benefit regardless of villain's decision.
In short, being faster than the opposing Pokemon means that we use fewer mixed strategies, and therefore have fewer opportunities to make mistakes. This is because we are more often in a position where a dominating strategy exists.
The Illusion of Choice
Choice items are the embodiment of risk/reward in competitive battling, but the word "choice" is a misnomer. Sometimes, one (or more) attacks are never an option. The best illustration of this idea is Earthquake. Consider the following scenario:
1. We have a Choice Scarf Garchomp.
2. Our opponent has a Heatran. Villain also has a 100% healthy Dragonite. Stealth Rocks is not in play.
Unless we can deal with +1 Dragonite, Earthquake is never an option in this situation. A good opponent will know this.
Turn Zero
On Pokemon Showdown, the battle begins before the first turn. You can view your opponent's Pokemon, and can therefore tailor your lead to gain an advantage. For example, against a team of physical threats, I lead with Gyarados for an immediate Intimidate. I otherwise never lead with Gyarados.
You should also identify your most valuable Pokemon based on likely favourable match ups. For example, if I see a Gliscor, Gengar is automatically my MVP (unless I have even more compelling options), because I can switch in with impunity, and use Substitute as Gliscor switches out. From turn one onwards, it is a sequential game to engineer this precise match up.
Additional content to come when I'm more inspired and less lazy.
Related: Pokemon Breeding: A Lesson in Economics
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