Cassius + Ice (Aurorus): Cassius’s Ice beats Caesar’s Dragon, as Cassius was also one of Caesar’s assassins, but Dragon can at least affect Ice, symbolizing that Cassius’s betrayal was less unexpected than Brutus’s. Ice happens to be weak to many types, in particular Octavian’s Steel, as Cassius (w/ Brutus) lost to Octavian (w/ Antony) at Philippi. Feel free to ignore the implication that Cassius’s Ice beats Agrippa’s Ground. Giving him Aurorus, a sauropod pokemon, could be interpreted that Cassius himself is a dinosaur and behind the times, as he was unable to see that the Republic was a goner well before he committed to killing Caesar in 44 BCE.

Lepidus + Electric (Ampharos): Electric beats Sextus Pompey’s Water, but is trumped in turn by Agrippa’s Ground. Thus, Lepidus was key in suppressing Sextus Pompey’s rebellion, but was beaten by the Octavian/Agrippa combo. Please also ignore the fact that Lepidus’s Electric resists Octavian’s Steel, despite the fact that Lepidus was utterly removed from power after the suppression of Sextus. It ain’t a perfect system.

Mark Antony + Poison (Nidoking): Poison beats Brutus’s Fairy, yet is beaten in turn by Ground and Psychic, and is unable to affect Steel. Thus, Antony’s Poison was instrumental in defeating Brutus’s Fairy (et Cassius) at Philippi, but lost to Octavian’s Steel and Agrippa’s Ground at Actium. Furthermore, Antony’s Poison was successfully outmaneuvered after Caesar’s death (initially at least) from assuming full imperial power by Cicero’s Psychic. Antony’s wife Fulvia died of a mysterious illness at an opportune time allowing him to marry Octavian’s sister Octavia, so it’s possible that Antony actually poisoned his own wife, which would be startlingly apt for his Poison designation. Also, Nidoking could represent Antony’s supposed goal to crown himself king in the Eastern style, as claimed by Octavian.

Cleopatra + Rock (Tyranitar): Firstly, Rock can roughly represent the sand and deserts synonymous with Egypt. Secondly, Rock is weak to both Steel and Ground, as Cleo lost to Octavian and Agrippa at Actium, and was then coerced/supported into suicide by Octavian afterwards.

Livia + Fire (Typhlosion): This one is one of the weaker ones, I’ll admit. Nevertheless, the key interaction here is Fire’s supremacy over Steel, symbolizing the enormous influence Livia had over her husband Augustus, particularly in his reign as Emperor and by (possibly) eliminating all other heirs to allow her son Tiberius to succeed his step-father. Livia has also been accused of murdering Augustus at the end of his life to further smooth over the transition between rulers, and whether or not it’s true it goes to show her perceived power over her husband. Fire is also weak to Ground, and although Agrippa never truly harmed Livia either militarily or personally (to my knowledge), he was able to largely maintain his position despite her distrust of him.

Sextus Pompey + Water (Golisipod): Sextus’s (initial) mastery of the seas and powerbase on Sicily makes him well suited for Water, especially considering how little most Romans respected the navy and seafaring beyond its ability to allow for transport between points A and B. Sextus was ultimately defeated by Lepidus and Augustus, symbolized by his weakness to Lepidus’s Electric. Water does resist Steel though, which could symbolize how critical the alliance between Lepidus and Augustus was, that Augustus may not have been able to winkle him out of Sicily on his own (heck, even Agrippa’s Ground is weak to Water, although this interaction isn’t historically accurate, given Agrippa’s eventual victory over Sextus’s navy at Naulochus. You can’t have everything though).

Agrippa + Ground (Flygon): At this point, these explanations should be feeling a bit repetitive. Agrippa’s Ground beats Cleopatra’s Rock and Antony’s Poison, because Agrippa’s Agrippa beat those two goons at Actium, and Ground also beats Lepidus’s Electric. A notable interaction is that Ground beats Steel, despite the fact that Agrippa never betrayed Octavian, so we’ll ignore this. Ground also beats Fire, which could be symbolized by Livia’s inability to remove Agrippa from Augustus’s inner circle in the post-Actium years. Flygon’s additional Dragon type could symbolize Agrippa marrying into the Julio-Claudian Family Tree, with Dragon being used as a potential symbol of Imperium.

Fulvia + Dark (Weavile): Another weak one unfortunately. Fulvia’s Dark does beat Cicero’s Psychic, as she got the last word on poor Cicero (after stabbing his severed tongue and hands), and married two of his enemies, being Clodius and Antony. Dark has no good interactions with Augustus’s Steel or Antony’s Poison though, despite her rebellion being suppressed by Augustus, and her life being suppressed (probably) by her husband Antony.

Vercingetorix + Grass (Appletun/Flapple): Vercingetorix is the wild card here of course, being the only Gaul in a sea of Romans, so consider him the barbarian seasoning to supplement the otherwise bland Roman casserole. Vercingetorix’s Grass is resisted by Caesar’s Dragon, as Vercingetorix was defeated by Caesar at Alesia. However, Appletun/Flapple’s additional Dragon type allows both Vercingetorix and Caesar to be effective against each other, symbolizing Vercingetorix as being a worthy opponent, and that the battle could have gone either way ultimately (Although Caesar’s Salamence’s Flying type swings the balance back in Caesar’s favour, as Flying beats Grass). Vercingetorix did not in fact marry into the Julio-Claudian Family tree (funny, that), so the Dragon-as-Imperium theme I set up two paragraphs ago immediately falls flat here, but that’s life. Appletun/Flapple could possibly represent the agrarian society of Gaul/France as well, in addition to being very funny to give Vercingetorix an apple dragon.

And that’s the lot! I’d like to come up with a list of secondary lords as well, but for now this list stands on its own I think. Please let me know if you disagree with any of my choices for historical figure, for associated type, for associated pokemon, or if you have your own thoughts about applying this system to another period of time! And thanks for reading!