Historically, the Siege of Osaka in 1615 marked the conclusion of Japan's Sengoku (Warring States) period by re-affirming the dominance of the Tokugawa clan over the entire country. The Toyotomi clan which preceded the Tokugawa, established by the peasant-turned-warlord Toyotomi Hideyoshi, was wiped out when their seat of Osaka Castle finally fell - Hideyoshi's son Hideyori, whose authority had been usurped by the Tokugawa shogun Ieyasu while he was still a child, committed suicide with his mother Yodo-dono as the Tokugawa forces overran their fortress after a seven month siege, while Hideyori's eight-year-old son Kunimatsu was captured and ruthlessly beheaded by the Tokugawa soon afterwards.
However, things did not have to end that way. The first half of the siege (November 1614-January 1615) concluded with a negotiated peace settlement, where the Toyotomi swore allegiance to the Tokugawa and destroyed Osaka's outer defenses, most notably filling in their own moat. Historically, this just made it easier for the Tokugawa to finish them off when they broke the peace agreement three months later. Even then, Ieyasu was badly wounded by a spear thrust in a desperate Toyotomi sally late in the second half of the siege.
But what if...these two events proceed in the Toyotomi's favor? Say, if Toyotomi Hideyori were to correctly see that Tokugawa Ieyasu's peace offering would just make it easier to finish his clan off in the next round, and spurns him - perhaps Ieyasu's powerful Western-style cannons kill Hideyori's mother, as opposed to just a few of her handmaids as happened historically, and this well and truly pisses off the normally timid and mild-mannered Hideyori. Instead of the first half of the Siege of Osaka ending in a three-month ceasefire where the Toyotomi's defenses are weakened, the siege continues and the Toyotomi accelerate their plans for a glorious last stand. Led by Hideyori himself and brave, competent commanders such as Sanada Yukimura and Gotou Motosugu, the Toyotomi forces sally forth in the dead of winter, catch the Tokugawa by surprise, and inflict significant casualties - including Ieyasu himself, felled by a lucky spear thrust. Though the Tokugawa army still greatly outnumbers the Toyotomi, they retreat in disorder from Osaka's environs, demoralized by their heavy casualties and the shock of their wizened leader's death.
So what happens? The Tokugawa clan is now led in more than just name by Ieyasu's oldest surviving son (and coincidentally, Hideyori's father-in-law) Hidetada, a mediocre leader who lacked his father's political savvy and military talent. Ieyasu had officially abdicated the office of Shogun to Hidetada in 1605, but still reigned as the power behind his son's throne until his historical death in 1616; here, Hidetada is suddenly forced to stand on his own without his father's guidance, in a time of renewed turmoil. Hidetada's position is further threatened by his younger half-brother Matsudaira Tadateru, Ieyasu's favorite son, who is popular with the eastern daimyo (feudal lords) and may well capitalize on the opportunity to challenge Hidetada for their father's legacy in this moment of vulnerability.
On the flipside, the Toyotomi faction will have gone from being dead men walking to the accidental masters of western and central Japan. Many of the western daimyo - the Mori, Shimazu and Chosokabe being among their most prominent members - had previously supported the Toyotomi against Ieyasu in the earlier Sekigahara Campaign of 1600 and were marginalized under the new Tokugawa order for it; presented with the opportunity to overthrow the Tokugawa entirely and regain what they lost under Ieyasu, there is little chance that they won't help Toyotomi. (indeed, the Chosokabe clan which dominated Shikoku had already sided with the Toyotomi at Osaka historically, and were destroyed for it) Thus Japan will likely regress into a sort of condensed Sengoku period pitting Toyotomi Hideyori in the west, Matsudaira Tadateru in the east and north, and Tokugawa Hidetada caught between them both in the middle against one another.
Foreigners, too, will have a role to play. The Catholic Spanish and Portuguese would see an opportunity to regain influence in Japan with Toyotomi, who historically enjoyed broad support from the Christian (in feudal Japan, universally Catholic) daimyo during the Sekigahara Campaign: at a minimum, they can expect him to lift the restrictions his father Hideyoshi had imposed on Catholics and to give them exclusive trade privileges at the expense of their Protestant, generally pro-Tokugawa Dutch and English rivals. Said Protestant powers, and particularly the Dutch who cared far more about trade than proselytizing, would naturally find it in their interest to side with Hidetada or Matsudaira. Firearms have become ubiquitous throughout Japan by this point in time, but not cannons: the Tokugawa famously fielded batteries of powerful Western-styled and built cannons at Osaka Castle, and so all sides' backers will likely furnish them with artillery at the minimum.
Thank you for reading all the way to the conclusion! If you like what you've just read, then by all means, please leave a comment. For that matter, if you don't like what you read, leave a comment anyway. I would be happy to receive any questions, suggestions or (civil) criticism you might have.
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