It may be common in war to betray one side, but it's quite the achievement to betray every side. This is the unique claim to fame of the Athenian Alkibiades, of the wealthy and influential Alkmaionid clan, who began to make his presence felt in Athenian politics around 420 BC.

As a persuasive speaker and audacious leader, Alkibiades soon became a prominent figure, and was elected one of the generals to command the Athenian expedition to Sicily in 415 - the campaign he had himself advocated to the Assembly. However, while the fleet was on its way, Alkibiades was indicted in an escalating scandal revolving around the serial mutilation of herms (statues that marked boundaries and warded off evil) and the profanation of the Eleusinian mysteries. A message was sent after the fleet summoning Alkibiades back to Athens to face trial. Alkibiades didn't fancy his chances, and fled to Sparta instead. Betrayal number one.

According to Thucydides, he proceeded to tell the Spartans exactly how they could win the war that they would soon resume fighting against Athens. He became tight pals with high-ranking Spartans and allegedly even had an affair with the wife of one of the kings.

The Spartans realised that they would need a lot of money to fund a fleet to defeat Athens, and Alkibiades promised to get it for them. He went off to the Persian satrap to persuade him to fund the Spartan fleet. However, what he actually did at the satrapal court was advise the Persians on exactly how they might play divide and rule with the Greeks, keeping both Athens and Sparta weak in order to further their own aims. Betrayal number two.

At the same time, he started sending messages to Athens to imply that he would be able to secure Persian funding for their fleet - exactly what he had promised the Spartans - if they would only drop the charges against him and invite him home. Oh, and also that the Persians would probably prefer if Athens were not a democracy anymore, so could that be arranged? This was one of the main causes of the coup that led to the short-lived oligarchy of the Four Hundred. The other main cause was that the Athenian countryside was being continuously ravaged by the Spartans, who had set up a permanent fortress in Athenian territory, as Alkibiades had told them to do.

Now, Alkibiades obviously wouldn't be Alkibiades if he would just support this new regime that had been created more or less for his sake. Instead of returning home in triumph, he seems to have realised that the oligarchy wouldn't last, and sided with the Athenian fleet instead, which had already renounced the government at home. Betrayal number three. Amazingly, the Athenians still wanted him back.

Of course, being invited back to Athens and given a position as one of the main commanders of the Athenian fleet meant that Alkibiades went directly against the Persian policy to keep the Greeks divided and weak. Instead, he began actively fighting against the Spartan fleet that was now beginning to receive substantial Persian funding. Betrayal number four.

Some time after his return to Athens, the Athenians finally decided they were fed up with him, and threw him out a second time. He spent his final years living in his estate at the Hellespont, until the Spartans (allegedly) or the Persians (probably) had him murdered in his sleep.

I mean, I study Sengoku. Betrayal is everywhere.

So instead of the two well known ones (Akechi Mitsuhide killing Oda Nobunaga and Kobayakawa Hideyaki betraying Ishida Mitsunari at Sekigahara) let me mention someone less well known outside Japan. Also because last year's Taiga Drama touched on his story.

In 1582, Oda Nobunaga destroyed the famous Takeda clan of Kai province. One of the surviving Takeda vassal was the Sanada family located in Chiisagata area of Shinano province. Sanada Masayuki, the leader of the clan, decided to submit to Oda Nobunaga. Nobunaga, being Nobunga, accepted but took away one of Masayuki's three major castles, Numata Castle.

And then Nobunaga died of betrayal a month later, throwing his newly conquered realms of Kai and Shinano (old Takeda realms) into chaos. Taking advantage of this, Masayuki gathered under him as many local ex-Takeda vassals as he could. At the same time, the Hōjō decided to take this chance to move into west into Kai and north into Kōsuke (east of Shinano, which btw is just north of Kai). Masayuki waited for the Hōjō to beat up the remaining Oda forces in the region, before taking back Numata castle. Betrayal maybe? (the Oda kind of abandoned it as they pulled out, so you can argue it wasn't a betrayal)

The Uesugi then decided to take the opportunity to move south into Shinano. Masayuki immediately sided with the Uesugi. Betrayal? (I mean the Oda has abandoned Shinano)

Less than a month later as the Hōjō forces moved into Shinano to confront the Uesugi, Masayuki suddenly declared for the Hōjō. Betrayal.

The Hōjō then agreed with the Uesugi to divide up Shinano. Satisfied, they began to move south into Kai, and Masayuki was left behind to watch the Uesugi, who had to leave to deal with an internal rebellion.

In Kai, Tokugawa Ieyasu, who had moved in amidst the chaos, was now hard-pressed, being attacked by the Hōjō from the east and the north. So what did Masayuki do? He sided with Tokugawa Ieyasu, and ran amok in the Hōjō rear in Shinano. Betrayal.

As the tides turned against the Hōjō, they decided to negotiate a peace with the Tokugawa. Included in the settlement was for Numata Castle to be given ("back") to the Hōjō. Masayuki's answer was "I was not given Numata by the Tokugawa, I took it. Want me to give it up? Give me something in return." But to buy some preparation and time, Masayuki told Tokugawa Ieyasu "Hey, the Uesugi might be preparing to move south again". Tokugawa Ieyasu meanwhile had turned his attention west to the aftermath of Nobunaga's death, and had no choice but to temporarily let Masayuki hold onto Numata. Not only that, Masayuki convinced him that they need a new castle at Ueda, and since the Sanada was too pure to build a big, strong castle by itself, the Tokugawa's going to help.

And while all this was going on (and Hōjō was busy with the Uesugi again-good timing no?-and the Satake) Masayuki busied himself conquering a couple of neighbouring districts, including inviting one of the district's lord to play Go, and then assassinating him.

And after Tokugawa Ieyasu made peace with Toyotomi Hideyoshi at Komaki, the Hōjō went to Ieyasu and demanded he hand over Numata. Ieyasu now went to Masayuki again to give up Numata under threat of force. Masayuki's response was to declare independence and ally himself with the Uesugi -again, oh and did I mention he saw this coming and had sent his second son to the Uesugi as hostage half a year ago?-. Betrayal (so long and thanks for the castle).

Royally pissed off, Ieyasu sent his army to conquer the Sanada, facing off at the newly built Ueda castle, with the Hōjō moving to take back Numata by force. And both the Tokugawa and the Hōjō got their ass kicked.

And before the war could drag longer, Masayuki declared for Toyotomi Hideyoshi (the Uesugi did too so not a betrayal), forcing Ieyasu and the Hōjō to stop attacking him.

By betraying pretty much anyone and everyone, and played the big powers against each other, Sanada Masayuki managed to carve out an independent realm for himself and secure his place as an independent daimyō under Hideyoshi. He also defeated the Tokugawa forces at Ueda so badly that Ieyasu decided to make up with the Sanada by having the daughter of one of his most important generals marry Masayuki's heir Nobuyuki.

Masayuki would betray Ieyasu one last time in 1600. Having declared for the Tokugawa during the expedition on the Uesugi, on news that Ishida Mitsunari had rose up and formed an anti-Tokugawa alliance, he switched sides to Mitsunari (his heir Nobuyuki remained with the Tokugawa to ensure no matter which side won, the Sanada would survive, another common tactic). And as a large Tokugawa force of 38,000 under Ieyasu's son Hidetada (who's going to be the second Shogun a few years later) passed by Ueda Castle, Masayuki holed up in the castle with 7,000 men, baited the Tokugawa forces to attack, and then kicked their ass -again-. Not only was Ueda Castle unconquered, this (and the weather) forced Hidetada's forces to be late for Sekigahara.

This should have given Mitsunari the advantage in numbers at Sekigahara. Unfortunately due to the betrayal of Kyōgoku Takatsugu, Mitsunari was only able to have numerical parity at Sekigahara (he in fact was outnumbered). And then because of the betrayal of Kikkawa Hiroie and famously Kobayakawa Hideaki, he lost the battle. So many betrayals...

In the aftermath, Ieyasu's punishment for Masayuki was to exile him to a little village, where he spent the rest of his days.

While this is a theme probably best for proper single instances of treason and betrayal, what first came to mind was rather: what the hell was wrong with Charles of Navarre? I wish I had a paper explaining him to me, but seriously. I mean this was the 14th century, switching allegiances was easier than putting a new shirt on, but he managed to stand out for deceit, treachery, double dealings, poisoning attempts and so forth even for the period. I feel like I'd like to read a psychology, rather than a history paper about this, the somewhat underwhelmingly named Charles the Bad.